# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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
#  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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Fe N3 O3'
_chemical_formula_weight         357.19

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.8538(3)
_cell_length_b                   12.9015(4)
_cell_length_c                   12.7365(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.033(3)
_cell_angle_gamma                90.00
_cell_volume                     1606.99(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_T_max  0.9104
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            16438
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3153
_reflns_number_gt                2690
_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)+(0.0375P)²+0.9692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3153
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.23257(3) 0.48776(2) 0.88575(2) 0.03329(12) Uani 1 1 d . . .
N2 N 0.24406(19) 0.33087(14) 0.40847(14) 0.0399(4) Uani 1 1 d . . .
C1 C 0.2175(2) 0.41878(17) 0.74232(18) 0.0385(5) Uani 1 1 d . . .
C3 C 0.1538(3) 0.34078(19) 0.8899(2) 0.0490(6) Uani 1 1 d . . .
H3 H 0.0982 0.3142 0.9427 0.059 Uiso 1 1 calc R . .
N1 N 0.1967(2) 0.41041(15) 0.54741(15) 0.0436(5) Uani 1 1 d . . .
C4 C 0.2970(3) 0.33697(18) 0.89686(19) 0.0477(6) Uani 1 1 d . . .
H4 H 0.3585 0.3071 0.9554 0.057 Uiso 1 1 calc R . .
C2 C 0.1040(2) 0.39100(18) 0.79477(19) 0.0444(6) Uani 1 1 d . . .
H2 H 0.0077 0.4046 0.7694 0.053 Uiso 1 1 calc R . .
C14 C 0.2960(2) 0.38417(18) 0.49245(18) 0.0431(5) Uani 1 1 d . . .
H14 H 0.3879 0.4005 0.5099 0.052 Uiso 1 1 calc R . .
C5 C 0.3376(2) 0.38417(18) 0.8061(2) 0.0440(5) Uani 1 1 d . . .
H5 H 0.4318 0.3920 0.7899 0.053 Uiso 1 1 calc R . .
C13 C 0.1065(3) 0.32240(19) 0.41122(19) 0.0464(6) Uani 1 1 d . . .
H13 H 0.0445 0.2886 0.3618 0.056 Uiso 1 1 calc R . .
C12 C 0.0771(3) 0.37171(19) 0.4982(2) 0.0486(6) Uani 1 1 d . . .
H12 H -0.0088 0.3782 0.5207 0.058 Uiso 1 1 calc R . .
C11 C 0.2136(4) 0.4773(2) 0.6420(2) 0.0629(8) Uani 1 1 d . . .
H11A H 0.1385 0.5264 0.6374 0.075 Uiso 1 1 calc R . .
H11B H 0.2977 0.5165 0.6428 0.075 Uiso 1 1 calc R . .
C7 C 0.1282(3) 0.6185(2) 0.9147(3) 0.0712(9) Uani 1 1 d . . .
H7 H 0.0324 0.6334 0.8886 0.085 Uiso 1 1 calc R . .
C9 C 0.3161(3) 0.5648(2) 1.0177(2) 0.0624(8) Uani 1 1 d . . .
H9 H 0.3762 0.5344 1.0768 0.075 Uiso 1 1 calc R . .
C8 C 0.1753(3) 0.5698(2) 1.0097(2) 0.0642(8) Uani 1 1 d . . .
H8 H 0.1185 0.5440 1.0621 0.077 Uiso 1 1 calc R . .
C10 C 0.3581(3) 0.6089(2) 0.9283(3) 0.0676(9) Uani 1 1 d . . .
H10 H 0.4530 0.6159 0.9135 0.081 Uiso 1 1 calc R . .
C6 C 0.2420(4) 0.6430(2) 0.8630(2) 0.0733(10) Uani 1 1 d . . .
H6 H 0.2407 0.6787 0.7949 0.088 Uiso 1 1 calc R . .
N3 N 0.3220(2) 0.61595(18) 0.3935(2) 0.0585(6) Uani 1 1 d . . .
O1 O 0.3751(3) 0.6162(2) 0.4862(2) 0.0965(8) Uani 1 1 d . . .
O2 O 0.2003(2) 0.6049(2) 0.3743(2) 0.1068(10) Uani 1 1 d . . .
C15 C 0.3214(3) 0.2922(2) 0.3251(2) 0.0633(8) Uani 1 1 d . . .
H15A H 0.2917 0.2222 0.3061 0.076 Uiso 1 1 calc R . .
H15B H 0.4178 0.2895 0.3520 0.076 Uiso 1 1 calc R . .
C16 C 0.3027(5) 0.3583(3) 0.2295(3) 0.1120(16) Uani 1 1 d . . .
H16A H 0.2070 0.3642 0.2049 0.168 Uiso 1 1 calc R . .
H16B H 0.3492 0.3277 0.1752 0.168 Uiso 1 1 calc R . .
H16C H 0.3398 0.4259 0.2465 0.168 Uiso 1 1 calc R . .
O3 O 0.3973(3) 0.6259(4) 0.3278(3) 0.1517(15) Uani 1 1 d . . .


_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 C1 2.021(2) . ?
Fe1 C10 2.025(3) . ?
Fe1 C6 2.027(3) . ?
Fe1 C7 2.033(3) . ?
Fe1 C5 2.036(2) . ?
Fe1 C2 2.036(2) . ?
Fe1 C8 2.037(3) . ?
Fe1 C9 2.038(3) . ?
Fe1 C4 2.046(2) . ?
Fe1 C3 2.052(2) . ?
N2 C14 1.321(3) . ?
N2 C13 1.365(3) . ?
N2 C15 1.469(3) . ?
C1 C2 1.417(3) . ?
C1 C5 1.423(3) . ?
C1 C11 1.481(3) . ?
C3 C4 1.404(4) . ?
C3 C2 1.408(4) . ?
C3 H3 0.9800 . ?
N1 C14 1.315(3) . ?
N1 C12 1.360(3) . ?
N1 C11 1.474(3) . ?
C4 C5 1.407(3) . ?
C4 H4 0.9800 . ?
C2 H2 0.9800 . ?
C14 H14 0.9300 . ?
C5 H5 0.9800 . ?
C13 C12 1.339(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 C8 1.392(4) . ?
C7 C6 1.405(5) . ?
C7 H7 0.9800 . ?
C9 C8 1.380(4) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9800 . ?
C8 H8 0.9800 . ?
C10 C6 1.400(5) . ?
C10 H10 0.9800 . ?
C6 H6 0.9800 . ?
N3 O3 1.192(3) . ?
N3 O2 1.203(3) . ?
N3 O1 1.231(3) . ?
C15 C16 1.480(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C1 Fe1 C10 123.80(12) . . ?
C1 Fe1 C6 107.78(11) . . ?
C10 Fe1 C6 40.43(13) . . ?
C1 Fe1 C7 123.13(12) . . ?
C10 Fe1 C7 67.50(13) . . ?
C6 Fe1 C7 40.48(14) . . ?
C1 Fe1 C5 41.08(9) . . ?
C10 Fe1 C5 107.96(11) . . ?
C6 Fe1 C5 122.83(12) . . ?
C7 Fe1 C5 159.18(14) . . ?
C1 Fe1 C2 40.89(9) . . ?
C10 Fe1 C2 160.44(13) . . ?
C6 Fe1 C2 124.10(13) . . ?
C7 Fe1 C2 108.59(11) . . ?
C5 Fe1 C2 68.47(9) . . ?
C1 Fe1 C8 158.87(12) . . ?
C10 Fe1 C8 67.04(12) . . ?
C6 Fe1 C8 67.64(12) . . ?
C7 Fe1 C8 40.01(13) . . ?
C5 Fe1 C8 158.94(12) . . ?
C2 Fe1 C8 123.21(11) . . ?
C1 Fe1 C9 159.71(12) . . ?
C10 Fe1 C9 39.76(13) . . ?
C6 Fe1 C9 67.37(13) . . ?
C7 Fe1 C9 66.91(12) . . ?
C5 Fe1 C9 123.54(11) . . ?
C2 Fe1 C9 158.24(12) . . ?
C8 Fe1 C9 39.58(12) . . ?
C1 Fe1 C4 68.39(9) . . ?
C10 Fe1 C4 122.73(12) . . ?
C6 Fe1 C4 158.40(14) . . ?
C7 Fe1 C4 159.42(14) . . ?
C5 Fe1 C4 40.33(10) . . ?
C2 Fe1 C4 67.83(10) . . ?
C8 Fe1 C4 123.60(12) . . ?
C9 Fe1 C4 108.42(11) . . ?
C1 Fe1 C3 68.31(9) . . ?
C10 Fe1 C3 157.92(13) . . ?
C6 Fe1 C3 160.17(14) . . ?
C7 Fe1 C3 124.10(13) . . ?
C5 Fe1 C3 67.88(10) . . ?
C2 Fe1 C3 40.30(10) . . ?
C8 Fe1 C3 108.57(11) . . ?
C9 Fe1 C3 123.03(12) . . ?
C4 Fe1 C3 40.08(11) . . ?
C14 N2 C13 108.0(2) . . ?
C14 N2 C15 125.4(2) . . ?
C13 N2 C15 126.6(2) . . ?
C2 C1 C5 107.5(2) . . ?
C2 C1 C11 126.6(2) . . ?
C5 C1 C11 125.8(2) . . ?
C2 C1 Fe1 70.13(13) . . ?
C5 C1 Fe1 70.01(13) . . ?
C11 C1 Fe1 123.15(16) . . ?
C4 C3 C2 108.2(2) . . ?
C4 C3 Fe1 69.72(14) . . ?
C2 C3 Fe1 69.24(13) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C14 N1 C12 108.6(2) . . ?
C14 N1 C11 124.7(2) . . ?
C12 N1 C11 126.6(2) . . ?
C3 C4 C5 108.5(2) . . ?
C3 C4 Fe1 70.20(14) . . ?
C5 C4 Fe1 69.44(13) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe1 C4 H4 125.7 . . ?
C3 C2 C1 108.1(2) . . ?
C3 C2 Fe1 70.46(13) . . ?
C1 C2 Fe1 68.98(12) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.0 . . ?
N1 C14 N2 109.0(2) . . ?
N1 C14 H14 125.5 . . ?
N2 C14 H14 125.5 . . ?
C4 C5 C1 107.7(2) . . ?
C4 C5 Fe1 70.23(13) . . ?
C1 C5 Fe1 68.91(12) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 126.1 . . ?
Fe1 C5 H5 126.1 . . ?
C12 C13 N2 107.4(2) . . ?
C12 C13 H13 126.3 . . ?
N2 C13 H13 126.3 . . ?
C13 C12 N1 107.0(2) . . ?
C13 C12 H12 126.5 . . ?
N1 C12 H12 126.5 . . ?
N1 C11 C1 113.3(2) . . ?
N1 C11 H11A 108.9 . . ?
C1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C8 C7 C6 107.9(3) . . ?
C8 C7 Fe1 70.14(16) . . ?
C6 C7 Fe1 69.53(16) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe1 C7 H7 126.0 . . ?
C8 C9 C10 108.7(3) . . ?
C8 C9 Fe1 70.17(16) . . ?
C10 C9 Fe1 69.63(16) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 H9 125.7 . . ?
Fe1 C9 H9 125.7 . . ?
C9 C8 C7 108.1(3) . . ?
C9 C8 Fe1 70.25(15) . . ?
C7 C8 Fe1 69.86(16) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Fe1 C8 H8 125.9 . . ?
C9 C10 C6 108.3(3) . . ?
C9 C10 Fe1 70.61(16) . . ?
C6 C10 Fe1 69.85(16) . . ?
C9 C10 H10 125.9 . . ?
C6 C10 H10 125.9 . . ?
Fe1 C10 H10 125.9 . . ?
C10 C6 C7 107.0(3) . . ?
C10 C6 Fe1 69.72(16) . . ?
C7 C6 Fe1 69.99(17) . . ?
C10 C6 H6 126.5 . . ?
C7 C6 H6 126.5 . . ?
Fe1 C6 H6 126.5 . . ?
O3 N3 O2 124.1(3) . . ?
O3 N3 O1 116.5(3) . . ?
O2 N3 O1 119.4(3) . . ?
N2 C15 C16 112.0(3) . . ?
N2 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 992962'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 Fe N3 O3'
_chemical_formula_weight         371.22

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           monoclinic
_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                   12.5421(7)
_cell_length_b                   14.1112(8)
_cell_length_c                   9.8489(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.506(5)
_cell_angle_gamma                90.00
_cell_volume                     1741.43(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8786
_exptl_absorpt_correction_T_max  0.9167
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            17552
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3414
_reflns_number_gt                2770
_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)+(0.1718P)²+3.1699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     217
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0840
_refine_ls_wR_factor_ref         0.2652
_refine_ls_wR_factor_gt          0.2461
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.085
_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 0.06897(6) 0.07787(5) 0.25639(7) 0.0455(3) Uani 1 1 d . . .
C1 C 0.2243(5) 0.0733(4) 0.3149(8) 0.0655(18) Uani 1 1 d . . .
C2 C 0.2042(4) 0.0086(4) 0.2072(6) 0.0552(13) Uani 1 1 d . . .
H2 H 0.2369 0.0094 0.1186 0.066 Uiso 1 1 calc R . .
C3 C 0.1291(4) -0.0571(4) 0.2505(6) 0.0495(12) Uani 1 1 d . . .
H3 H 0.0988 -0.1095 0.1960 0.059 Uiso 1 1 calc R . .
C4 C 0.1016(4) -0.0336(4) 0.3842(6) 0.0563(13) Uani 1 1 d . . .
H4 H 0.0500 -0.0671 0.4386 0.068 Uiso 1 1 calc R . .
C5 C 0.1602(6) 0.0454(5) 0.4243(6) 0.0693(18) Uani 1 1 d . . .
H5 H 0.1578 0.0771 0.5126 0.083 Uiso 1 1 calc R . .
C6 C 0.0346(7) 0.2136(5) 0.2047(9) 0.083(2) Uani 1 1 d . . .
H6 H 0.0831 0.2679 0.2131 0.100 Uiso 1 1 calc R . .
C7 C 0.0205(6) 0.1508(6) 0.0874(7) 0.081(2) Uani 1 1 d . . .
H7 H 0.0577 0.1549 0.0021 0.097 Uiso 1 1 calc R . .
C8 C -0.0562(6) 0.0852(5) 0.1191(7) 0.0703(19) Uani 1 1 d . . .
H8 H -0.0822 0.0333 0.0603 0.084 Uiso 1 1 calc R . .
C9 C -0.0910(5) 0.1052(5) 0.2504(7) 0.0648(16) Uani 1 1 d . . .
H9 H -0.1444 0.0688 0.2980 0.078 Uiso 1 1 calc R . .
C10 C -0.0362(5) 0.1826(5) 0.3019(7) 0.0645(16) Uani 1 1 d . . .
H10 H -0.0444 0.2107 0.3919 0.077 Uiso 1 1 calc R . .
C11 C 0.2962(6) 0.1568(5) 0.3085(12) 0.104(3) Uani 1 1 d . . .
H11A H 0.2957 0.1800 0.2157 0.125 Uiso 1 1 calc R . .
H11B H 0.2693 0.2070 0.3650 0.125 Uiso 1 1 calc R . .
C12 C 0.4777(8) 0.0750(7) 0.2934(12) 0.103(3) Uani 1 1 d . . .
H12A H 0.4669 0.0421 0.2121 0.124 Uiso 1 1 calc R . .
C13 C 0.5657(7) 0.0747(6) 0.3759(13) 0.110(4) Uani 1 1 d . . .
H13A H 0.6278 0.0409 0.3613 0.132 Uiso 1 1 calc R . .
C14 C 0.4543(6) 0.1651(5) 0.4594(8) 0.079(2) Uani 1 1 d . . .
H14A H 0.4235 0.2091 0.5162 0.095 Uiso 1 1 calc R . .
C15 C 0.6306(9) 0.1502(8) 0.5856(14) 0.137(4) Uani 1 1 d DU . .
H15A H 0.6755 0.0943 0.5941 0.165 Uiso 1 1 calc R . .
H15B H 0.5965 0.1581 0.6713 0.165 Uiso 1 1 calc R . .
C16 C 0.7013(9) 0.2337(8) 0.5664(14) 0.145(4) Uani 1 1 d DU . .
H16A H 0.7272 0.2523 0.6567 0.173 Uiso 1 1 calc R . .
H16B H 0.7627 0.2100 0.5205 0.173 Uiso 1 1 calc R . .
C17 C 0.6704(11) 0.3206(9) 0.4971(15) 0.161(5) Uani 1 1 d DU . .
H17A H 0.7309 0.3621 0.4946 0.242 Uiso 1 1 calc R . .
H17B H 0.6147 0.3510 0.5449 0.242 Uiso 1 1 calc R . .
H17C H 0.6450 0.3063 0.4060 0.242 Uiso 1 1 calc R . .
N1 N 0.4067(5) 0.1342(4) 0.3542(8) 0.0814(18) Uani 1 1 d . . .
N2 N 0.5494(4) 0.1315(4) 0.4836(6) 0.0622(13) Uani 1 1 d . . .
N3 N 0.3273(12) 0.3839(5) 0.3268(13) 0.174(5) Uani 1 1 d DU . .
O1 O 0.4137(12) 0.3629(9) 0.2857(16) 0.216(5) Uani 1 1 d DU . .
O2 O 0.3117(13) 0.3794(9) 0.4447(13) 0.246(6) Uani 1 1 d DU . .
O3 O 0.2728(14) 0.4053(10) 0.229(2) 0.260(7) Uani 1 1 d DU . .


_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 C1 2.008(6) . ?
Fe1 C5 2.022(5) . ?
Fe1 C6 2.023(6) . ?
Fe1 C7 2.028(6) . ?
Fe1 C8 2.029(6) . ?
Fe1 C2 2.034(5) . ?
Fe1 C9 2.041(6) . ?
Fe1 C10 2.044(6) . ?
Fe1 C4 2.045(5) . ?
Fe1 C3 2.051(5) . ?
C1 C2 1.415(9) . ?
C1 C5 1.427(11) . ?
C1 C11 1.488(9) . ?
C2 C3 1.401(8) . ?
C2 H2 0.9800 . ?
C3 C4 1.416(8) . ?
C3 H3 0.9800 . ?
C4 C5 1.383(9) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C10 1.404(11) . ?
C6 C7 1.460(11) . ?
C6 H6 0.9800 . ?
C7 C8 1.381(11) . ?
C7 H7 0.9800 . ?
C8 C9 1.411(10) . ?
C8 H8 0.9800 . ?
C9 C10 1.375(10) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 N1 1.474(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.342(16) . ?
C12 N1 1.377(11) . ?
C12 H12A 0.9300 . ?
C13 N2 1.353(12) . ?
C13 H13A 0.9300 . ?
C14 N1 1.251(9) . ?
C14 N2 1.297(8) . ?
C14 H14A 0.9300 . ?
C15 N2 1.423(10) . ?
C15 C16 1.492(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.448(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N3 O2 1.187(9) . ?
N3 O3 1.193(9) . ?
N3 O1 1.210(9) . ?

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
C1 Fe1 C5 41.5(3) . . ?
C1 Fe1 C6 107.2(3) . . ?
C5 Fe1 C6 121.8(3) . . ?
C1 Fe1 C7 120.3(3) . . ?
C5 Fe1 C7 157.7(4) . . ?
C6 Fe1 C7 42.3(3) . . ?
C1 Fe1 C8 154.9(4) . . ?
C5 Fe1 C8 161.8(4) . . ?
C6 Fe1 C8 68.5(3) . . ?
C7 Fe1 C8 39.8(3) . . ?
C1 Fe1 C2 41.0(3) . . ?
C5 Fe1 C2 68.8(3) . . ?
C6 Fe1 C2 124.5(3) . . ?
C7 Fe1 C2 105.8(3) . . ?
C8 Fe1 C2 119.6(3) . . ?
C1 Fe1 C9 162.6(3) . . ?
C5 Fe1 C9 125.9(3) . . ?
C6 Fe1 C9 67.4(3) . . ?
C7 Fe1 C9 67.7(3) . . ?
C8 Fe1 C9 40.6(3) . . ?
C2 Fe1 C9 155.8(3) . . ?
C1 Fe1 C10 126.0(3) . . ?
C5 Fe1 C10 109.4(3) . . ?
C6 Fe1 C10 40.4(3) . . ?
C7 Fe1 C10 68.9(3) . . ?
C8 Fe1 C10 67.8(3) . . ?
C2 Fe1 C10 162.3(3) . . ?
C9 Fe1 C10 39.4(3) . . ?
C1 Fe1 C4 68.5(2) . . ?
C5 Fe1 C4 39.8(3) . . ?
C6 Fe1 C4 156.6(3) . . ?
C7 Fe1 C4 160.2(3) . . ?
C8 Fe1 C4 125.3(3) . . ?
C2 Fe1 C4 68.3(2) . . ?
C9 Fe1 C4 109.5(3) . . ?
C10 Fe1 C4 122.3(3) . . ?
C1 Fe1 C3 68.0(2) . . ?
C5 Fe1 C3 67.5(2) . . ?
C6 Fe1 C3 161.2(3) . . ?
C7 Fe1 C3 123.1(3) . . ?
C8 Fe1 C3 107.6(2) . . ?
C2 Fe1 C3 40.1(2) . . ?
C9 Fe1 C3 122.5(3) . . ?
C10 Fe1 C3 156.9(3) . . ?
C4 Fe1 C3 40.4(2) . . ?
C2 C1 C5 107.5(5) . . ?
C2 C1 C11 124.6(8) . . ?
C5 C1 C11 127.8(8) . . ?
C2 C1 Fe1 70.5(3) . . ?
C5 C1 Fe1 69.8(3) . . ?
C11 C1 Fe1 123.0(4) . . ?
C3 C2 C1 107.4(5) . . ?
C3 C2 Fe1 70.6(3) . . ?
C1 C2 Fe1 68.5(3) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
Fe1 C2 H2 126.3 . . ?
C2 C3 C4 108.8(5) . . ?
C2 C3 Fe1 69.3(3) . . ?
C4 C3 Fe1 69.5(3) . . ?
C2 C3 H3 125.6 . . ?
C4 C3 H3 125.6 . . ?
Fe1 C3 H3 125.6 . . ?
C5 C4 C3 107.9(5) . . ?
C5 C4 Fe1 69.2(3) . . ?
C3 C4 Fe1 70.0(3) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
Fe1 C4 H4 126.1 . . ?
C4 C5 C1 108.4(5) . . ?
C4 C5 Fe1 71.0(3) . . ?
C1 C5 Fe1 68.8(3) . . ?
C4 C5 H5 125.8 . . ?
C1 C5 H5 125.8 . . ?
Fe1 C5 H5 125.8 . . ?
C10 C6 C7 107.0(7) . . ?
C10 C6 Fe1 70.6(4) . . ?
C7 C6 Fe1 69.0(4) . . ?
C10 C6 H6 126.5 . . ?
C7 C6 H6 126.5 . . ?
Fe1 C6 H6 126.5 . . ?
C8 C7 C6 106.8(6) . . ?
C8 C7 Fe1 70.2(4) . . ?
C6 C7 Fe1 68.7(4) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
Fe1 C7 H7 126.6 . . ?
C7 C8 C9 108.6(6) . . ?
C7 C8 Fe1 70.0(4) . . ?
C9 C8 Fe1 70.2(3) . . ?
C7 C8 H8 125.7 . . ?
C9 C8 H8 125.7 . . ?
Fe1 C8 H8 125.7 . . ?
C10 C9 C8 109.2(7) . . ?
C10 C9 Fe1 70.4(4) . . ?
C8 C9 Fe1 69.3(4) . . ?
C10 C9 H9 125.4 . . ?
C8 C9 H9 125.4 . . ?
Fe1 C9 H9 125.4 . . ?
C9 C10 C6 108.4(6) . . ?
C9 C10 Fe1 70.2(3) . . ?
C6 C10 Fe1 69.0(3) . . ?
C9 C10 H10 125.8 . . ?
C6 C10 H10 125.8 . . ?
Fe1 C10 H10 125.8 . . ?
N1 C11 C1 112.3(6) . . ?
N1 C11 H11A 109.2 . . ?
C1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 N1 105.6(9) . . ?
C13 C12 H12A 127.2 . . ?
N1 C12 H12A 127.2 . . ?
C12 C13 N2 108.9(7) . . ?
C12 C13 H13A 125.5 . . ?
N2 C13 H13A 125.5 . . ?
N1 C14 N2 115.2(7) . . ?
N1 C14 H14A 122.4 . . ?
N2 C14 H14A 122.4 . . ?
N2 C15 C16 117.9(8) . . ?
N2 C15 H15A 107.8 . . ?
C16 C15 H15A 107.8 . . ?
N2 C15 H15B 107.8 . . ?
C16 C15 H15B 107.8 . . ?
H15A C15 H15B 107.2 . . ?
C17 C16 C15 125.5(9) . . ?
C17 C16 H16A 106.0 . . ?
C15 C16 H16A 106.0 . . ?
C17 C16 H16B 106.0 . . ?
C15 C16 H16B 106.0 . . ?
H16A C16 H16B 106.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 N1 C12 106.2(7) . . ?
C14 N1 C11 125.8(8) . . ?
C12 N1 C11 128.0(8) . . ?
C14 N2 C13 104.0(7) . . ?
C14 N2 C15 133.4(8) . . ?
C13 N2 C15 122.4(9) . . ?
O2 N3 O3 133(2) . . ?
O2 N3 O1 120.1(16) . . ?
O3 N3 O1 106.4(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 999264'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 Fe N3 O4'
_chemical_formula_weight         389.23

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.6098(3)
_cell_length_b                   9.9244(4)
_cell_length_c                   12.4142(4)
_cell_angle_alpha                94.402(3)
_cell_angle_beta                 97.669(3)
_cell_angle_gamma                107.436(3)
_cell_volume                     879.69(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8715
_exptl_absorpt_correction_T_max  0.8937
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            17675
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3447
_reflns_number_gt                3123
_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)+(0.0406P)²+0.3291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3447
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.55574(3) 0.75604(2) 0.900607(19) 0.02865(9) Uani 1 1 d . . .
N1 N 0.3447(2) 0.65041(17) 0.54718(12) 0.0354(3) Uani 1 1 d . . .
N2 N 0.1648(2) 0.63635(16) 0.39431(11) 0.0325(3) Uani 1 1 d . . .
N3 N 0.3550(2) 0.13322(19) 0.62618(16) 0.0466(4) Uani 1 1 d . . .
C1 C 0.4076(2) 0.67764(19) 0.74938(14) 0.0313(4) Uani 1 1 d . . .
C2 C 0.3152(2) 0.7580(2) 0.80692(15) 0.0375(4) Uani 1 1 d . . .
H2 H 0.2868 0.8428 0.7845 0.045 Uiso 1 1 calc R . .
C3 C 0.2752(3) 0.6966(2) 0.90274(16) 0.0451(5) Uani 1 1 d . . .
H3 H 0.2145 0.7315 0.9587 0.054 Uiso 1 1 calc R . .
C4 C 0.3396(3) 0.5779(2) 0.90561(16) 0.0451(5) Uani 1 1 d . . .
H4 H 0.3307 0.5157 0.9637 0.054 Uiso 1 1 calc R . .
C5 C 0.4211(3) 0.56405(19) 0.81063(16) 0.0387(4) Uani 1 1 d . . .
H5 H 0.4770 0.4905 0.7909 0.046 Uiso 1 1 calc R . .
C6 C 0.8221(3) 0.8630(2) 0.88250(19) 0.0516(5) Uani 1 1 d . . .
H6 H 0.8728 0.8665 0.8139 0.062 Uiso 1 1 calc R . .
C7 C 0.7375(3) 0.9582(2) 0.92538(19) 0.0511(5) Uani 1 1 d . . .
H7 H 0.7180 1.0397 0.8915 0.061 Uiso 1 1 calc R . .
C8 C 0.6854(3) 0.9164(2) 1.02519(18) 0.0494(5) Uani 1 1 d . . .
H8 H 0.6231 0.9637 1.0728 0.059 Uiso 1 1 calc R . .
C9 C 0.7375(3) 0.7950(2) 1.04471(17) 0.0473(5) Uani 1 1 d . . .
H9 H 0.7184 0.7430 1.1083 0.057 Uiso 1 1 calc R . .
C10 C 0.8223(3) 0.7616(2) 0.95681(19) 0.0498(5) Uani 1 1 d . . .
H10 H 0.8729 0.6822 0.9485 0.060 Uiso 1 1 calc R . .
C11 C 0.4843(3) 0.7134(2) 0.64718(15) 0.0426(5) Uani 1 1 d . . .
H11A H 0.5280 0.8160 0.6486 0.051 Uiso 1 1 calc R . .
H11B H 0.5907 0.6791 0.6447 0.051 Uiso 1 1 calc R . .
C12 C 0.2693(3) 0.5084(2) 0.50772(16) 0.0394(4) Uani 1 1 d . . .
H12 H 0.2918 0.4328 0.5407 0.047 Uiso 1 1 calc R . .
C13 C 0.1573(3) 0.4995(2) 0.41269(15) 0.0389(4) Uani 1 1 d . . .
H13 H 0.0873 0.4164 0.3675 0.047 Uiso 1 1 calc R . .
C14 C 0.2789(2) 0.72499(19) 0.47730(14) 0.0333(4) Uani 1 1 d . . .
H14 H 0.3082 0.8235 0.4852 0.040 Uiso 1 1 calc R . .
C15 C 0.0676(3) 0.6747(2) 0.29495(15) 0.0405(4) Uani 1 1 d . . .
H15 H -0.0646 0.6180 0.2843 0.049 Uiso 1 1 calc R . .
C16 C 0.0809(4) 0.8298(3) 0.30980(19) 0.0582(6) Uani 1 1 d . . .
H16A H 0.0235 0.8483 0.3713 0.087 Uiso 1 1 calc R . .
H16B H 0.0178 0.8528 0.2449 0.087 Uiso 1 1 calc R . .
H16C H 0.2098 0.8872 0.3227 0.087 Uiso 1 1 calc R . .
C17 C 0.1480(3) 0.6362(3) 0.19663(16) 0.0590(6) Uani 1 1 d . . .
H17A H 0.1349 0.5365 0.1900 0.088 Uiso 1 1 calc R . .
H17B H 0.2779 0.6904 0.2056 0.088 Uiso 1 1 calc R . .
H17C H 0.0823 0.6571 0.1318 0.088 Uiso 1 1 calc R . .
O1 O 0.3854(3) 0.26070(18) 0.64390(18) 0.0764(5) Uani 1 1 d . . .
O1W O 0.0386(3) 0.17073(18) 0.38926(17) 0.0756(5) Uani 1 1 d . . .
O2 O 0.3966(5) 0.0670(3) 0.6967(2) 0.1329(11) Uani 1 1 d . . .
O3 O 0.2866(3) 0.0680(2) 0.53461(18) 0.0945(7) Uani 1 1 d . . .
H1W1 H 0.1124 0.1409 0.4329 0.142 Uiso 1 1 d R . .
H1W2 H -0.0690 0.1088 0.3851 0.142 Uiso 1 1 d R . .


_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 C1 2.0213(17) . ?
Fe1 C5 2.0312(18) . ?
Fe1 C4 2.0340(19) . ?
Fe1 C10 2.0380(19) . ?
Fe1 C6 2.038(2) . ?
Fe1 C2 2.0397(17) . ?
Fe1 C7 2.040(2) . ?
Fe1 C3 2.0419(19) . ?
Fe1 C8 2.043(2) . ?
Fe1 C9 2.0435(19) . ?
N1 C14 1.325(2) . ?
N1 C12 1.375(2) . ?
N1 C11 1.480(2) . ?
N2 C14 1.324(2) . ?
N2 C13 1.380(2) . ?
N2 C15 1.487(2) . ?
N3 O2 1.199(3) . ?
N3 O1 1.213(2) . ?
N3 O3 1.228(3) . ?
C1 C2 1.423(3) . ?
C1 C5 1.428(3) . ?
C1 C11 1.490(3) . ?
C2 C3 1.406(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.406(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.420(3) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C7 1.403(3) . ?
C6 C10 1.417(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.406(3) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.341(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.507(3) . ?
C15 C17 1.509(3) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1W H1W1 0.8606 . ?
O1W H1W2 0.8563 . ?

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
C1 Fe1 C5 41.27(7) . . ?
C1 Fe1 C4 68.92(8) . . ?
C5 Fe1 C4 40.88(8) . . ?
C1 Fe1 C10 127.10(8) . . ?
C5 Fe1 C10 108.05(8) . . ?
C4 Fe1 C10 119.77(9) . . ?
C1 Fe1 C6 107.57(8) . . ?
C5 Fe1 C6 119.44(9) . . ?
C4 Fe1 C6 154.10(10) . . ?
C10 Fe1 C6 40.67(9) . . ?
C1 Fe1 C2 41.01(7) . . ?
C5 Fe1 C2 68.81(8) . . ?
C4 Fe1 C2 68.13(8) . . ?
C10 Fe1 C2 165.02(9) . . ?
C6 Fe1 C2 127.01(9) . . ?
C1 Fe1 C7 118.97(8) . . ?
C5 Fe1 C7 153.63(9) . . ?
C4 Fe1 C7 164.26(9) . . ?
C10 Fe1 C7 67.84(9) . . ?
C6 Fe1 C7 40.25(9) . . ?
C2 Fe1 C7 108.06(9) . . ?
C1 Fe1 C3 68.62(7) . . ?
C5 Fe1 C3 68.50(8) . . ?
C4 Fe1 C3 40.36(9) . . ?
C10 Fe1 C3 153.60(9) . . ?
C6 Fe1 C3 164.25(10) . . ?
C2 Fe1 C3 40.29(8) . . ?
C7 Fe1 C3 127.03(9) . . ?
C1 Fe1 C8 153.18(8) . . ?
C5 Fe1 C8 164.50(9) . . ?
C4 Fe1 C8 127.00(9) . . ?
C10 Fe1 C8 67.67(9) . . ?
C6 Fe1 C8 67.79(9) . . ?
C2 Fe1 C8 119.24(8) . . ?
C7 Fe1 C8 40.28(9) . . ?
C3 Fe1 C8 108.27(9) . . ?
C1 Fe1 C9 164.86(8) . . ?
C5 Fe1 C9 127.01(8) . . ?
C4 Fe1 C9 108.27(8) . . ?
C10 Fe1 C9 40.30(9) . . ?
C6 Fe1 C9 68.06(9) . . ?
C2 Fe1 C9 153.11(9) . . ?
C7 Fe1 C9 67.78(9) . . ?
C3 Fe1 C9 119.54(9) . . ?
C8 Fe1 C9 40.22(9) . . ?
C14 N1 C12 108.57(15) . . ?
C14 N1 C11 124.51(16) . . ?
C12 N1 C11 126.83(16) . . ?
C14 N2 C13 108.09(15) . . ?
C14 N2 C15 126.98(16) . . ?
C13 N2 C15 124.86(15) . . ?
O2 N3 O1 121.0(2) . . ?
O2 N3 O3 117.6(2) . . ?
O1 N3 O3 121.4(2) . . ?
C2 C1 C5 107.58(16) . . ?
C2 C1 C11 124.99(17) . . ?
C5 C1 C11 127.34(17) . . ?
C2 C1 Fe1 70.19(10) . . ?
C5 C1 Fe1 69.74(10) . . ?
C11 C1 Fe1 122.88(13) . . ?
C3 C2 C1 108.15(17) . . ?
C3 C2 Fe1 69.94(11) . . ?
C1 C2 Fe1 68.80(9) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 125.9 . . ?
C2 C3 C4 108.47(17) . . ?
C2 C3 Fe1 69.77(11) . . ?
C4 C3 Fe1 69.51(11) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 H3 125.8 . . ?
Fe1 C3 H3 125.8 . . ?
C3 C4 C5 108.42(17) . . ?
C3 C4 Fe1 70.12(11) . . ?
C5 C4 Fe1 69.45(11) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 107.37(17) . . ?
C4 C5 Fe1 69.67(11) . . ?
C1 C5 Fe1 68.99(10) . . ?
C4 C5 H5 126.3 . . ?
C1 C5 H5 126.3 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C10 107.6(2) . . ?
C7 C6 Fe1 69.94(12) . . ?
C10 C6 Fe1 69.66(12) . . ?
C7 C6 H6 126.2 . . ?
C10 C6 H6 126.2 . . ?
Fe1 C6 H6 126.2 . . ?
C6 C7 C8 108.3(2) . . ?
C6 C7 Fe1 69.81(12) . . ?
C8 C7 Fe1 69.97(12) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
Fe1 C7 H7 125.9 . . ?
C9 C8 C7 108.2(2) . . ?
C9 C8 Fe1 69.92(11) . . ?
C7 C8 Fe1 69.75(12) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Fe1 C8 H8 125.9 . . ?
C8 C9 C10 107.9(2) . . ?
C8 C9 Fe1 69.86(11) . . ?
C10 C9 Fe1 69.64(11) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
Fe1 C9 H9 126.1 . . ?
C9 C10 C6 108.0(2) . . ?
C9 C10 Fe1 70.06(11) . . ?
C6 C10 Fe1 69.67(11) . . ?
C9 C10 H10 126.0 . . ?
C6 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
N1 C11 C1 112.54(15) . . ?
N1 C11 H11A 109.1 . . ?
C1 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 N1 107.02(16) . . ?
C13 C12 H12 126.5 . . ?
N1 C12 H12 126.5 . . ?
C12 C13 N2 107.40(16) . . ?
C12 C13 H13 126.3 . . ?
N2 C13 H13 126.3 . . ?
N2 C14 N1 108.91(16) . . ?
N2 C14 H14 125.5 . . ?
N1 C14 H14 125.5 . . ?
N2 C15 C16 110.61(16) . . ?
N2 C15 C17 109.05(16) . . ?
C16 C15 C17 112.53(19) . . ?
N2 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C17 C15 H15 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H1W1 O1W H1W2 104.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 1008574'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 Fe2 N8 O7'
_chemical_formula_weight         706.33

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.0600(2)
_cell_length_b                   12.5298(5)
_cell_length_c                   20.6252(5)
_cell_angle_alpha                80.833(3)
_cell_angle_beta                 87.615(2)
_cell_angle_gamma                87.665(3)
_cell_volume                     1543.82(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8729
_exptl_absorpt_correction_T_max  0.9067
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            31116
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6075
_reflns_number_gt                4931
_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)+(0.1096P)²+1.7800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6075
_refine_ls_number_parameters     406
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2023
_refine_ls_wR_factor_gt          0.1896
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.212
_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 -0.03101(11) 0.64130(5) 0.15479(3) 0.0472(2) Uani 1 1 d . . .
C1 C 0.0045(8) 0.6841(4) 0.2446(2) 0.0505(10) Uani 1 1 d . . .
N1 N 0.0633(8) 0.8155(3) 0.3177(2) 0.0603(10) Uani 1 1 d . . .
N3 N 0.1556(8) 0.8495(4) 0.4094(2) 0.0647(11) Uani 1 1 d . . .
C4 C -0.0098(13) 0.5100(5) 0.2268(3) 0.0753(17) Uani 1 1 d . . .
H4A H -0.0628 0.4379 0.2243 0.090 Uiso 1 1 calc R . .
C2 C 0.2107(8) 0.6519(5) 0.2191(2) 0.0596(12) Uani 1 1 d . . .
H2A H 0.3397 0.6973 0.2101 0.072 Uiso 1 1 calc R . .
C5 C -0.1336(9) 0.5938(5) 0.2499(2) 0.0674(14) Uani 1 1 d . . .
H5A H -0.2871 0.5907 0.2668 0.081 Uiso 1 1 calc R . .
C12 C 0.0033(10) 0.8081(4) 0.3792(3) 0.0612(12) Uani 1 1 d . . .
H12A H -0.1263 0.7783 0.3985 0.073 Uiso 1 1 calc R . .
N2 N 0.2621(9) 0.8621(5) 0.3060(3) 0.0820(15) Uani 1 1 d . . .
C3 C 0.2009(11) 0.5462(5) 0.2075(3) 0.0745(17) Uani 1 1 d . . .
H3A H 0.3215 0.5041 0.1894 0.089 Uiso 1 1 calc R . .
C11 C -0.0651(12) 0.7904(5) 0.2638(3) 0.0801(18) Uani 1 1 d . . .
H11A H -0.0470 0.8468 0.2261 0.096 Uiso 1 1 calc R . .
H11B H -0.2205 0.7894 0.2771 0.096 Uiso 1 1 calc R . .
C13 C 0.3121(11) 0.8812(5) 0.3639(4) 0.0824(18) Uani 1 1 d . . .
H13A H 0.4414 0.9132 0.3724 0.099 Uiso 1 1 calc R . .
C14 C 0.1470(15) 0.8611(7) 0.4795(3) 0.101(2) Uani 1 1 d . . .
H14A H 0.0141 0.8305 0.5002 0.152 Uiso 1 1 calc R . .
H14B H 0.1482 0.9364 0.4834 0.152 Uiso 1 1 calc R . .
H14C H 0.2730 0.8240 0.5005 0.152 Uiso 1 1 calc R . .
Fe2 Fe 0.44212(12) 0.17528(5) 0.12691(3) 0.0541(2) Uani 1 1 d . . .
N4 N 0.3684(7) 0.3034(3) 0.31326(18) 0.0512(9) Uani 1 1 d . . .
N6 N 0.1926(6) 0.3993(3) 0.37512(18) 0.0508(9) Uani 1 1 d . . .
C15 C 0.3850(8) 0.2624(4) 0.2005(2) 0.0499(10) Uani 1 1 d . . .
C26 C 0.1820(9) 0.3139(4) 0.3451(2) 0.0550(11) Uani 1 1 d . . .
H26A H 0.0621 0.2694 0.3466 0.066 Uiso 1 1 calc R . .
N5 N 0.5071(7) 0.3821(4) 0.3212(2) 0.0619(11) Uani 1 1 d . . .
C16 C 0.5324(10) 0.3172(4) 0.1520(3) 0.0673(14) Uani 1 1 d . . .
H16A H 0.6831 0.3376 0.1588 0.081 Uiso 1 1 calc R . .
C27 C 0.3955(8) 0.4379(4) 0.3596(2) 0.0583(12) Uani 1 1 d . . .
H27A H 0.4490 0.4976 0.3748 0.070 Uiso 1 1 calc R . .
C25 C 0.4316(11) 0.2223(4) 0.2705(3) 0.0679(15) Uani 1 1 d . . .
H25A H 0.3508 0.1570 0.2852 0.082 Uiso 1 1 calc R . .
H25B H 0.5880 0.2038 0.2743 0.082 Uiso 1 1 calc R . .
C19 C 0.1858(9) 0.2516(5) 0.1693(3) 0.0633(13) Uani 1 1 d . . .
H19A H 0.0538 0.2168 0.1905 0.076 Uiso 1 1 calc R . .
C18 C 0.2078(13) 0.2975(5) 0.1030(3) 0.0810(19) Uani 1 1 d . . .
H18A H 0.0954 0.3000 0.0700 0.097 Uiso 1 1 calc R . .
C17 C 0.4195(14) 0.3374(5) 0.0923(3) 0.0825(19) Uani 1 1 d . . .
H17A H 0.4813 0.3728 0.0500 0.099 Uiso 1 1 calc R . .
C28 C 0.0222(10) 0.4422(6) 0.4173(3) 0.0790(17) Uani 1 1 d . . .
H28A H -0.1062 0.3991 0.4201 0.119 Uiso 1 1 calc R . .
H28B H -0.0166 0.5156 0.3991 0.119 Uiso 1 1 calc R . .
H28C H 0.0776 0.4401 0.4605 0.119 Uiso 1 1 calc R . .
C22 C 0.5474(16) 0.0929(7) 0.0534(4) 0.101(2) Uani 1 1 d U . .
H22A H 0.5530 0.1246 0.0067 0.122 Uiso 1 1 calc R . .
C9 C -0.1161(18) 0.5942(6) 0.0704(3) 0.097(3) Uani 1 1 d . . .
H9A H -0.1206 0.5195 0.0620 0.116 Uiso 1 1 calc R . .
C21 C 0.7062(17) 0.0953(7) 0.0921(6) 0.111(2) Uani 1 1 d U . .
H21A H 0.8458 0.1301 0.0779 0.133 Uiso 1 1 calc R . .
C8 C 0.0621(12) 0.6594(13) 0.0593(3) 0.123(4) Uani 1 1 d . . .
H8A H 0.2076 0.6416 0.0405 0.148 Uiso 1 1 calc R . .
C10 C -0.2851(12) 0.6520(11) 0.0937(3) 0.105(3) Uani 1 1 d . . .
H10A H -0.4326 0.6247 0.1061 0.127 Uiso 1 1 calc R . .
C7 C -0.011(3) 0.7582(10) 0.0765(4) 0.138(5) Uani 1 1 d . . .
H7A H 0.0767 0.8231 0.0729 0.166 Uiso 1 1 calc R . .
N7 N 0.5315(8) 0.6551(4) 0.4501(2) 0.0639(11) Uani 1 1 d . . .
O1 O 0.6077(9) 0.6472(4) 0.3952(2) 0.0939(15) Uani 1 1 d . . .
O2 O 0.3600(9) 0.6136(5) 0.4700(3) 0.1134(19) Uani 1 1 d . . .
C6 C -0.224(3) 0.7502(11) 0.0977(4) 0.143(5) Uani 1 1 d . . .
H6A H -0.3174 0.8079 0.1126 0.172 Uiso 1 1 calc R . .
O3 O 0.6334(9) 0.7103(5) 0.4833(3) 0.1052(17) Uani 1 1 d . . .
C20 C 0.666(2) 0.0524(7) 0.1497(5) 0.116(2) Uani 1 1 d U . .
H20A H 0.7687 0.0452 0.1857 0.139 Uiso 1 1 calc R . .
C24 C 0.446(2) 0.0151(5) 0.1548(5) 0.128(3) Uani 1 1 d U . .
H24A H 0.3689 -0.0271 0.1925 0.153 Uiso 1 1 calc R . .
C23 C 0.3712(16) 0.0463(6) 0.0843(5) 0.112(2) Uani 1 1 d U . .
H23A H 0.2319 0.0307 0.0657 0.134 Uiso 1 1 calc R . .
N8 N 0.8408(11) 0.0690(5) 0.3441(5) 0.098(2) Uani 1 1 d . . .
O4 O 0.8380(19) 0.1425(8) 0.3724(4) 0.195(5) Uani 1 1 d . . .
O5 O 0.7371(13) 0.0031(6) 0.3526(7) 0.209(4) Uani 1 1 d U . .
O6 O 0.968(2) 0.0931(11) 0.2955(6) 0.219(5) Uani 1 1 d . . .
O1W O 0.622(2) 0.8903(12) 0.5612(7) 0.271(6) Uani 1 1 d . . .
H1W1 H 0.4950 0.8808 0.5795 0.407 Uiso 1 1 d R . .
H1W2 H 0.6264 0.8387 0.5389 0.407 Uiso 1 1 d R . .


_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 C7 2.003(7) . ?
Fe1 C8 2.006(6) . ?
Fe1 C10 2.017(6) . ?
Fe1 C6 2.022(8) . ?
Fe1 C9 2.018(6) . ?
Fe1 C1 2.031(4) . ?
Fe1 C5 2.036(5) . ?
Fe1 C4 2.037(5) . ?
Fe1 C2 2.039(5) . ?
Fe1 C3 2.039(6) . ?
C1 C2 1.404(7) . ?
C1 C5 1.422(8) . ?
C1 C11 1.490(7) . ?
N1 C12 1.295(7) . ?
N1 N2 1.356(7) . ?
N1 C11 1.464(7) . ?
N3 C12 1.303(7) . ?
N3 C13 1.333(8) . ?
N3 C14 1.474(7) . ?
C4 C3 1.394(10) . ?
C4 C5 1.399(9) . ?
C4 H4A 0.9800 . ?
C2 C3 1.387(8) . ?
C2 H2A 0.9800 . ?
C5 H5A 0.9800 . ?
C12 H12A 0.9300 . ?
N2 C13 1.306(9) . ?
C3 H3A 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
Fe2 C21 2.021(8) . ?
Fe2 C20 2.021(8) . ?
Fe2 C24 1.997(7) . ?
Fe2 C15 2.017(4) . ?
Fe2 C23 2.028(6) . ?
Fe2 C22 2.035(6) . ?
Fe2 C16 2.031(5) . ?
Fe2 C19 2.031(5) . ?
Fe2 C17 2.044(6) . ?
Fe2 C18 2.061(6) . ?
N4 C26 1.295(6) . ?
N4 N5 1.355(6) . ?
N4 C25 1.478(6) . ?
N6 C26 1.325(6) . ?
N6 C27 1.347(6) . ?
N6 C28 1.464(6) . ?
C15 C19 1.413(7) . ?
C15 C16 1.423(8) . ?
C15 C25 1.486(7) . ?
C26 H26A 0.9300 . ?
N5 C27 1.292(6) . ?
C16 C17 1.418(9) . ?
C16 H16A 0.9800 . ?
C27 H27A 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C19 C18 1.398(9) . ?
C19 H19A 0.9800 . ?
C18 C17 1.392(10) . ?
C18 H18A 0.9800 . ?
C17 H17A 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C22 C21 1.281(12) . ?
C22 C23 1.328(12) . ?
C22 H22A 0.9800 . ?
C9 C10 1.347(12) . ?
C9 C8 1.370(13) . ?
C9 H9A 0.9800 . ?
C21 C20 1.242(13) . ?
C21 H21A 0.9800 . ?
C8 C7 1.392(16) . ?
C8 H8A 0.9800 . ?
C10 C6 1.316(15) . ?
C10 H10A 0.9800 . ?
C7 C6 1.347(17) . ?
C7 H7A 0.9800 . ?
N7 O2 1.208(6) . ?
N7 O1 1.223(6) . ?
N7 O3 1.244(7) . ?
C6 H6A 0.9800 . ?
C20 C24 1.425(14) . ?
C20 H20A 0.9800 . ?
C24 C23 1.527(14) . ?
C24 H24A 0.9800 . ?
C23 H23A 0.9800 . ?
N8 O5 1.046(8) . ?
N8 O4 1.165(11) . ?
N8 O6 1.244(12) . ?
O1W H1W1 0.8500 . ?
O1W H1W2 0.8500 . ?

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
C7 Fe1 C8 40.6(5) . . ?
C7 Fe1 C10 64.8(4) . . ?
C8 Fe1 C10 66.1(3) . . ?
C7 Fe1 C6 39.1(5) . . ?
C8 Fe1 C6 67.0(4) . . ?
C10 Fe1 C6 38.0(5) . . ?
C7 Fe1 C9 66.3(3) . . ?
C8 Fe1 C9 39.8(4) . . ?
C10 Fe1 C9 39.0(4) . . ?
C6 Fe1 C9 65.5(4) . . ?
C7 Fe1 C1 117.5(4) . . ?
C8 Fe1 C1 148.3(4) . . ?
C10 Fe1 C1 133.6(3) . . ?
C6 Fe1 C1 111.6(3) . . ?
C9 Fe1 C1 170.9(3) . . ?
C7 Fe1 C5 148.9(6) . . ?
C8 Fe1 C5 169.3(5) . . ?
C10 Fe1 C5 111.3(3) . . ?
C6 Fe1 C5 117.9(4) . . ?
C9 Fe1 C5 131.7(3) . . ?
C1 Fe1 C5 40.9(2) . . ?
C7 Fe1 C4 170.5(6) . . ?
C8 Fe1 C4 130.8(5) . . ?
C10 Fe1 C4 118.0(4) . . ?
C6 Fe1 C4 148.4(6) . . ?
C9 Fe1 C4 109.5(3) . . ?
C1 Fe1 C4 68.0(2) . . ?
C5 Fe1 C4 40.2(3) . . ?
C7 Fe1 C2 111.5(3) . . ?
C8 Fe1 C2 116.5(3) . . ?
C10 Fe1 C2 171.8(4) . . ?
C6 Fe1 C2 134.5(5) . . ?
C9 Fe1 C2 147.7(3) . . ?
C1 Fe1 C2 40.38(19) . . ?
C5 Fe1 C2 67.7(2) . . ?
C4 Fe1 C2 67.0(2) . . ?
C7 Fe1 C3 132.9(6) . . ?
C8 Fe1 C3 108.7(3) . . ?
C10 Fe1 C3 148.2(4) . . ?
C6 Fe1 C3 171.5(6) . . ?
C9 Fe1 C3 116.3(3) . . ?
C1 Fe1 C3 67.9(2) . . ?
C5 Fe1 C3 67.7(3) . . ?
C4 Fe1 C3 40.0(3) . . ?
C2 Fe1 C3 39.8(2) . . ?
C2 C1 C5 106.9(5) . . ?
C2 C1 C11 128.6(5) . . ?
C5 C1 C11 124.5(5) . . ?
C2 C1 Fe1 70.1(3) . . ?
C5 C1 Fe1 69.7(3) . . ?
C11 C1 Fe1 125.5(4) . . ?
C12 N1 N2 110.9(5) . . ?
C12 N1 C11 127.8(5) . . ?
N2 N1 C11 121.1(5) . . ?
C12 N3 C13 106.1(5) . . ?
C12 N3 C14 125.7(6) . . ?
C13 N3 C14 128.2(6) . . ?
C3 C4 C5 108.7(5) . . ?
C3 C4 Fe1 70.1(3) . . ?
C5 C4 Fe1 69.9(3) . . ?
C3 C4 H4A 125.7 . . ?
C5 C4 H4A 125.7 . . ?
Fe1 C4 H4A 125.7 . . ?
C3 C2 C1 109.0(5) . . ?
C3 C2 Fe1 70.1(3) . . ?
C1 C2 Fe1 69.5(3) . . ?
C3 C2 H2A 125.5 . . ?
C1 C2 H2A 125.5 . . ?
Fe1 C2 H2A 125.5 . . ?
C4 C5 C1 107.4(5) . . ?
C4 C5 Fe1 70.0(3) . . ?
C1 C5 Fe1 69.3(3) . . ?
C4 C5 H5A 126.3 . . ?
C1 C5 H5A 126.3 . . ?
Fe1 C5 H5A 126.3 . . ?
N1 C12 N3 108.3(5) . . ?
N1 C12 H12A 125.9 . . ?
N3 C12 H12A 125.9 . . ?
C13 N2 N1 102.8(5) . . ?
C4 C3 C2 108.0(5) . . ?
C4 C3 Fe1 70.0(3) . . ?
C2 C3 Fe1 70.1(3) . . ?
C4 C3 H3A 126.0 . . ?
C2 C3 H3A 126.0 . . ?
Fe1 C3 H3A 126.0 . . ?
N1 C11 C1 112.0(5) . . ?
N1 C11 H11A 109.2 . . ?
C1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C13 N3 111.9(6) . . ?
N2 C13 H13A 124.0 . . ?
N3 C13 H13A 124.0 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 Fe2 C20 35.8(4) . . ?
C21 Fe2 C24 65.4(4) . . ?
C20 Fe2 C24 41.5(4) . . ?
C21 Fe2 C15 135.5(3) . . ?
C20 Fe2 C15 112.6(3) . . ?
C24 Fe2 C15 114.8(3) . . ?
C21 Fe2 C23 64.7(4) . . ?
C20 Fe2 C23 69.0(4) . . ?
C24 Fe2 C23 44.6(4) . . ?
C15 Fe2 C23 149.0(3) . . ?
C21 Fe2 C22 36.8(4) . . ?
C20 Fe2 C22 63.0(4) . . ?
C24 Fe2 C22 67.3(3) . . ?
C15 Fe2 C22 171.5(3) . . ?
C23 Fe2 C22 38.2(3) . . ?
C21 Fe2 C16 110.7(3) . . ?
C20 Fe2 C16 113.6(3) . . ?
C24 Fe2 C16 144.2(4) . . ?
C15 Fe2 C16 41.2(2) . . ?
C23 Fe2 C16 169.1(4) . . ?
C22 Fe2 C16 132.4(3) . . ?
C21 Fe2 C19 175.4(4) . . ?
C20 Fe2 C19 140.0(4) . . ?
C24 Fe2 C19 112.5(3) . . ?
C15 Fe2 C19 40.9(2) . . ?
C23 Fe2 C19 117.2(3) . . ?
C22 Fe2 C19 147.1(3) . . ?
C16 Fe2 C19 68.3(2) . . ?
C21 Fe2 C17 115.3(4) . . ?
C20 Fe2 C17 141.7(4) . . ?
C24 Fe2 C17 175.0(4) . . ?
C15 Fe2 C17 68.5(2) . . ?
C23 Fe2 C17 130.7(4) . . ?
C22 Fe2 C17 110.0(3) . . ?
C16 Fe2 C17 40.7(3) . . ?
C19 Fe2 C17 67.1(3) . . ?
C21 Fe2 C18 144.4(4) . . ?
C20 Fe2 C18 178.4(4) . . ?
C24 Fe2 C18 137.0(4) . . ?
C15 Fe2 C18 68.3(2) . . ?
C23 Fe2 C18 109.5(3) . . ?
C22 Fe2 C18 116.3(3) . . ?
C16 Fe2 C18 68.0(3) . . ?
C19 Fe2 C18 40.0(2) . . ?
C17 Fe2 C18 39.6(3) . . ?
C26 N4 N5 111.1(4) . . ?
C26 N4 C25 127.6(5) . . ?
N5 N4 C25 121.2(4) . . ?
C26 N6 C27 105.5(4) . . ?
C26 N6 C28 127.5(5) . . ?
C27 N6 C28 126.9(5) . . ?
C19 C15 C16 107.0(5) . . ?
C19 C15 C25 126.2(5) . . ?
C16 C15 C25 126.8(5) . . ?
C19 C15 Fe2 70.1(3) . . ?
C16 C15 Fe2 70.0(3) . . ?
C25 C15 Fe2 124.4(3) . . ?
N4 C26 N6 107.7(4) . . ?
N4 C26 H26A 126.1 . . ?
N6 C26 H26A 126.1 . . ?
C27 N5 N4 103.6(4) . . ?
C17 C16 C15 107.1(6) . . ?
C17 C16 Fe2 70.1(3) . . ?
C15 C16 Fe2 68.9(3) . . ?
C17 C16 H16A 126.5 . . ?
C15 C16 H16A 126.5 . . ?
Fe2 C16 H16A 126.5 . . ?
N5 C27 N6 112.0(4) . . ?
N5 C27 H27A 124.0 . . ?
N6 C27 H27A 124.0 . . ?
N4 C25 C15 112.1(4) . . ?
N4 C25 H25A 109.2 . . ?
C15 C25 H25A 109.2 . . ?
N4 C25 H25B 109.2 . . ?
C15 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C18 C19 C15 109.1(6) . . ?
C18 C19 Fe2 71.2(3) . . ?
C15 C19 Fe2 69.0(3) . . ?
C18 C19 H19A 125.4 . . ?
C15 C19 H19A 125.4 . . ?
Fe2 C19 H19A 125.4 . . ?
C17 C18 C19 107.7(5) . . ?
C17 C18 Fe2 69.5(4) . . ?
C19 C18 Fe2 68.9(3) . . ?
C17 C18 H18A 126.1 . . ?
C19 C18 H18A 126.1 . . ?
Fe2 C18 H18A 126.1 . . ?
C18 C17 C16 109.1(6) . . ?
C18 C17 Fe2 70.8(4) . . ?
C16 C17 Fe2 69.2(3) . . ?
C18 C17 H17A 125.5 . . ?
C16 C17 H17A 125.5 . . ?
Fe2 C17 H17A 125.5 . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C22 C23 112.1(10) . . ?
C21 C22 Fe2 71.0(5) . . ?
C23 C22 Fe2 70.6(4) . . ?
C21 C22 H22A 123.9 . . ?
C23 C22 H22A 123.9 . . ?
Fe2 C22 H22A 123.9 . . ?
C10 C9 C8 107.6(8) . . ?
C10 C9 Fe1 70.5(4) . . ?
C8 C9 Fe1 69.6(4) . . ?
C10 C9 H9A 126.2 . . ?
C8 C9 H9A 126.2 . . ?
Fe1 C9 H9A 126.2 . . ?
C20 C21 C22 114.3(11) . . ?
C20 C21 Fe2 72.1(6) . . ?
C22 C21 Fe2 72.2(5) . . ?
C20 C21 H21A 122.8 . . ?
C22 C21 H21A 122.8 . . ?
Fe2 C21 H21A 122.8 . . ?
C9 C8 C7 105.6(8) . . ?
C9 C8 Fe1 70.6(4) . . ?
C7 C8 Fe1 69.6(4) . . ?
C9 C8 H8A 127.1 . . ?
C7 C8 H8A 127.1 . . ?
Fe1 C8 H8A 127.1 . . ?
C6 C10 C9 110.4(9) . . ?
C6 C10 Fe1 71.2(5) . . ?
C9 C10 Fe1 70.5(4) . . ?
C6 C10 H10A 124.8 . . ?
C9 C10 H10A 124.8 . . ?
Fe1 C10 H10A 124.8 . . ?
C6 C7 C8 108.4(9) . . ?
C6 C7 Fe1 71.2(5) . . ?
C8 C7 Fe1 69.8(5) . . ?
C6 C7 H7A 125.8 . . ?
C8 C7 H7A 125.8 . . ?
Fe1 C7 H7A 125.8 . . ?
O2 N7 O1 120.7(5) . . ?
O2 N7 O3 121.9(6) . . ?
O1 N7 O3 117.4(5) . . ?
C10 C6 C7 107.9(9) . . ?
C10 C6 Fe1 70.8(5) . . ?
C7 C6 Fe1 69.7(5) . . ?
C10 C6 H6A 126.0 . . ?
C7 C6 H6A 126.0 . . ?
Fe1 C6 H6A 126.0 . . ?
C21 C20 C24 108.8(10) . . ?
C21 C20 Fe2 72.1(5) . . ?
C24 C20 Fe2 68.3(5) . . ?
C21 C20 H20A 125.6 . . ?
C24 C20 H20A 125.6 . . ?
Fe2 C20 H20A 125.6 . . ?
C20 C24 C23 101.9(7) . . ?
C20 C24 Fe2 70.1(4) . . ?
C23 C24 Fe2 68.8(4) . . ?
C20 C24 H24A 128.9 . . ?
C23 C24 H24A 128.8 . . ?
Fe2 C24 H24A 128.9 . . ?
C22 C23 C24 102.8(8) . . ?
C22 C23 Fe2 71.2(4) . . ?
C24 C23 Fe2 66.6(4) . . ?
C22 C23 H23A 128.5 . . ?
C24 C23 H23A 128.5 . . ?
Fe2 C23 H23A 128.5 . . ?
O5 N8 O4 127.1(12) . . ?
O5 N8 O6 126.4(13) . . ?
O4 N8 O6 105.7(9) . . ?
H1W1 O1W H1W2 98.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.518
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.095
_database_code_depnum_ccdc_archive 'CCDC 997739'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Fe N5 O7'
_chemical_formula_weight         509.26

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   43.0383(15)
_cell_length_b                   5.8461(3)
_cell_length_c                   8.4347(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2122.22(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9002
_exptl_absorpt_correction_T_max  0.9273
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            11642
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3909
_reflns_number_gt                3416
_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)+(0.0558P)²+6.2330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   -0.01(4)
_refine_ls_number_reflns         3909
_refine_ls_number_parameters     307
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.096
_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 0.202263(17) 0.95881(16) 0.37363(15) 0.0402(3) Uani 1 1 d . . .
C1 C 0.15712(13) 0.8686(10) 0.3463(7) 0.0338(14) Uani 1 1 d . . .
C2 C 0.1644(2) 1.0590(17) 0.2502(12) 0.071(3) Uani 1 1 d . . .
H2 H 0.1545 1.2098 0.2550 0.085 Uiso 1 1 calc R . .
C3 C 0.1878(3) 0.993(3) 0.1467(13) 0.125(7) Uani 1 1 d . . .
H3 H 0.1975 1.0917 0.0666 0.150 Uiso 1 1 calc R . .
C4 C 0.1949(3) 0.778(3) 0.1732(16) 0.121(7) Uani 1 1 d . . .
H4 H 0.2111 0.6938 0.1161 0.145 Uiso 1 1 calc R . .
C5 C 0.17723(17) 0.6876(14) 0.2946(12) 0.065(2) Uani 1 1 d . . .
H5 H 0.1779 0.5306 0.3352 0.078 Uiso 1 1 calc R . .
C6 C 0.2130(2) 0.9827(17) 0.6090(10) 0.067(3) Uani 1 1 d . . .
H6 H 0.1997 0.9337 0.6967 0.081 Uiso 1 1 calc R . .
C7 C 0.21356(17) 1.1995(14) 0.5431(9) 0.0499(18) Uani 1 1 d . . .
H7 H 0.2003 1.3274 0.5756 0.060 Uiso 1 1 calc R . .
C8 C 0.2355(2) 1.2068(15) 0.4209(10) 0.062(2) Uani 1 1 d . . .
H8 H 0.2406 1.3392 0.3545 0.075 Uiso 1 1 calc R . .
C9 C 0.24828(18) 0.9871(16) 0.4082(12) 0.071(3) Uani 1 1 d . . .
H9 H 0.2645 0.9399 0.3336 0.086 Uiso 1 1 calc R . .
C10 C 0.2345(2) 0.8452(16) 0.5298(12) 0.072(3) Uani 1 1 d . . .
H10 H 0.2396 0.6855 0.5537 0.086 Uiso 1 1 calc R . .
C11 C 0.13414(15) 0.8500(19) 0.4749(9) 0.064(3) Uani 1 1 d . . .
H11A H 0.1336 0.9926 0.5337 0.077 Uiso 1 1 calc R . .
H11B H 0.1404 0.7297 0.5473 0.077 Uiso 1 1 calc R . .
C12 C 0.09494(16) 0.6139(14) 0.3174(9) 0.0516(18) Uani 1 1 d . . .
H12 H 0.1085 0.5022 0.2803 0.062 Uiso 1 1 calc R . .
C13 C 0.06434(17) 0.6271(13) 0.2888(10) 0.0521(19) Uani 1 1 d . . .
H13 H 0.0524 0.5240 0.2309 0.063 Uiso 1 1 calc R . .
C14 C 0.07763(16) 0.9207(15) 0.4385(9) 0.0515(19) Uani 1 1 d . . .
H14 H 0.0766 1.0529 0.4997 0.062 Uiso 1 1 calc R . .
C15 C 0.02187(16) 0.9070(15) 0.3606(17) 0.077(3) Uani 1 1 d . . .
H15A H 0.0206 1.0473 0.4193 0.116 Uiso 1 1 calc R . .
H15B H 0.0085 0.7949 0.4083 0.116 Uiso 1 1 calc R . .
H15C H 0.0154 0.9335 0.2531 0.116 Uiso 1 1 calc R . .
C16 C 0.09273(17) 0.4639(13) 0.7473(8) 0.0454(16) Uani 1 1 d . . .
C17 C 0.06239(17) 0.5718(13) 0.7646(9) 0.0488(17) Uani 1 1 d . . .
C18 C 0.05796(15) 0.7667(12) 0.8513(10) 0.0491(18) Uani 1 1 d . . .
H18 H 0.0382 0.8312 0.8580 0.059 Uiso 1 1 calc R . .
C19 C 0.08231(17) 0.8670(12) 0.9281(8) 0.0437(16) Uani 1 1 d . . .
C20 C 0.11234(15) 0.7728(12) 0.9235(7) 0.0408(15) Uani 1 1 d . . .
H20 H 0.1286 0.8416 0.9782 0.049 Uiso 1 1 calc R . .
C21 C 0.11710(14) 0.5792(12) 0.8377(8) 0.0433(17) Uani 1 1 d . . .
N1 N 0.10247(12) 0.7985(11) 0.4127(6) 0.0463(15) Uani 1 1 d . . .
N2 N 0.05405(12) 0.8231(10) 0.3620(9) 0.0478(13) Uani 1 1 d . . .
N3 N 0.03549(18) 0.4731(14) 0.6903(9) 0.0653(19) Uani 1 1 d . . .
N4 N 0.07770(16) 1.0713(12) 1.0229(8) 0.0545(16) Uani 1 1 d . . .
N5 N 0.14814(15) 0.4767(11) 0.8320(8) 0.0512(17) Uani 1 1 d U . .
O1 O 0.09841(15) 0.2960(11) 0.6609(9) 0.0718(17) Uani 1 1 d . . .
O2 O 0.03708(15) 0.2902(15) 0.6280(10) 0.096(3) Uani 1 1 d . . .
O3 O 0.01120(15) 0.5789(13) 0.6942(12) 0.102(3) Uani 1 1 d . . .
O4 O 0.05087(13) 1.1531(11) 1.0253(8) 0.0697(17) Uani 1 1 d . . .
O5 O 0.09880(15) 1.1491(12) 1.0969(8) 0.0720(18) Uani 1 1 d . . .
O6 O 0.15113(19) 0.2803(15) 0.844(2) 0.145(4) Uani 1 1 d U . .
O7 O 0.16898(16) 0.5931(15) 0.8136(12) 0.115(3) Uani 1 1 d . . .


_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 C9 2.009(8) . ?
Fe1 C4 2.019(10) . ?
Fe1 C2 2.022(8) . ?
Fe1 C3 2.023(11) . ?
Fe1 C10 2.024(7) . ?
Fe1 C1 2.026(5) . ?
Fe1 C5 2.029(8) . ?
Fe1 C6 2.043(8) . ?
Fe1 C7 2.064(7) . ?
Fe1 C8 2.077(8) . ?
C1 C2 1.411(11) . ?
C1 C5 1.435(9) . ?
C1 C11 1.472(9) . ?
C2 C3 1.389(18) . ?
C2 H2 0.9800 . ?
C3 C4 1.31(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.381(18) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C7 1.384(12) . ?
C6 C10 1.394(13) . ?
C6 H6 0.9800 . ?
C7 C8 1.399(11) . ?
C7 H7 0.9800 . ?
C8 C9 1.400(12) . ?
C8 H8 0.9800 . ?
C9 C10 1.447(14) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 N1 1.491(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.341(10) . ?
C12 N1 1.384(9) . ?
C12 H12 0.9300 . ?
C13 N2 1.375(10) . ?
C13 H13 0.9300 . ?
C14 N1 1.304(9) . ?
C14 N2 1.331(9) . ?
C14 H14 0.9300 . ?
C15 N2 1.469(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O1 1.247(9) . ?
C16 C17 1.458(10) . ?
C16 C21 1.461(10) . ?
C17 C18 1.367(11) . ?
C17 N3 1.437(10) . ?
C18 C19 1.365(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.406(9) . ?
C19 N4 1.451(10) . ?
C20 C21 1.359(10) . ?
C20 H20 0.9300 . ?
C21 N5 1.465(8) . ?
N3 O2 1.193(10) . ?
N3 O3 1.215(10) . ?
N4 O5 1.192(8) . ?
N4 O4 1.250(8) . ?
N5 O7 1.137(9) . ?
N5 O6 1.159(10) . ?

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
C9 Fe1 C4 108.7(4) . . ?
C9 Fe1 C2 147.8(4) . . ?
C4 Fe1 C2 66.0(6) . . ?
C9 Fe1 C3 115.6(5) . . ?
C4 Fe1 C3 37.9(6) . . ?
C2 Fe1 C3 40.2(5) . . ?
C9 Fe1 C10 42.0(4) . . ?
C4 Fe1 C10 118.8(6) . . ?
C2 Fe1 C10 169.3(5) . . ?
C3 Fe1 C10 149.2(6) . . ?
C9 Fe1 C1 169.5(3) . . ?
C4 Fe1 C1 67.5(3) . . ?
C2 Fe1 C1 40.8(3) . . ?
C3 Fe1 C1 67.9(4) . . ?
C10 Fe1 C1 130.2(4) . . ?
C9 Fe1 C5 129.5(3) . . ?
C4 Fe1 C5 39.9(5) . . ?
C2 Fe1 C5 68.2(4) . . ?
C3 Fe1 C5 66.7(5) . . ?
C10 Fe1 C5 108.7(4) . . ?
C1 Fe1 C5 41.4(3) . . ?
C9 Fe1 C6 68.3(4) . . ?
C4 Fe1 C6 152.3(7) . . ?
C2 Fe1 C6 131.6(5) . . ?
C3 Fe1 C6 169.2(7) . . ?
C10 Fe1 C6 40.1(4) . . ?
C1 Fe1 C6 110.2(3) . . ?
C5 Fe1 C6 119.5(4) . . ?
C9 Fe1 C7 67.1(3) . . ?
C4 Fe1 C7 166.9(6) . . ?
C2 Fe1 C7 110.4(4) . . ?
C3 Fe1 C7 131.3(6) . . ?
C10 Fe1 C7 67.1(4) . . ?
C1 Fe1 C7 118.8(3) . . ?
C5 Fe1 C7 152.3(4) . . ?
C6 Fe1 C7 39.4(3) . . ?
C9 Fe1 C8 40.1(4) . . ?
C4 Fe1 C8 129.4(5) . . ?
C2 Fe1 C8 117.0(4) . . ?
C3 Fe1 C8 108.9(4) . . ?
C10 Fe1 C8 68.4(4) . . ?
C1 Fe1 C8 149.9(3) . . ?
C5 Fe1 C8 167.1(3) . . ?
C6 Fe1 C8 67.0(3) . . ?
C7 Fe1 C8 39.5(3) . . ?
C2 C1 C5 105.9(7) . . ?
C2 C1 C11 129.0(8) . . ?
C5 C1 C11 125.1(7) . . ?
C2 C1 Fe1 69.4(4) . . ?
C5 C1 Fe1 69.4(4) . . ?
C11 C1 Fe1 125.4(4) . . ?
C3 C2 C1 107.7(10) . . ?
C3 C2 Fe1 69.9(6) . . ?
C1 C2 Fe1 69.8(4) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 109.0(10) . . ?
C4 C3 Fe1 70.9(8) . . ?
C2 C3 Fe1 69.9(6) . . ?
C4 C3 H3 125.5 . . ?
C2 C3 H3 125.5 . . ?
Fe1 C3 H3 125.5 . . ?
C3 C4 C5 111.5(10) . . ?
C3 C4 Fe1 71.2(7) . . ?
C5 C4 Fe1 70.5(5) . . ?
C3 C4 H4 124.2 . . ?
C5 C4 H4 124.2 . . ?
Fe1 C4 H4 124.2 . . ?
C4 C5 C1 105.9(10) . . ?
C4 C5 Fe1 69.6(6) . . ?
C1 C5 Fe1 69.2(4) . . ?
C4 C5 H5 127.0 . . ?
C1 C5 H5 127.0 . . ?
Fe1 C5 H5 127.0 . . ?
C7 C6 C10 109.0(8) . . ?
C7 C6 Fe1 71.1(5) . . ?
C10 C6 Fe1 69.2(5) . . ?
C7 C6 H6 125.5 . . ?
C10 C6 H6 125.5 . . ?
Fe1 C6 H6 125.5 . . ?
C6 C7 C8 109.5(8) . . ?
C6 C7 Fe1 69.5(4) . . ?
C8 C7 Fe1 70.7(4) . . ?
C6 C7 H7 125.2 . . ?
C8 C7 H7 125.2 . . ?
Fe1 C7 H7 125.2 . . ?
C7 C8 C9 107.1(8) . . ?
C7 C8 Fe1 69.8(4) . . ?
C9 C8 Fe1 67.4(4) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
Fe1 C8 H8 126.5 . . ?
C8 C9 C10 108.1(8) . . ?
C8 C9 Fe1 72.6(5) . . ?
C10 C9 Fe1 69.5(4) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe1 C9 H9 125.9 . . ?
C6 C10 C9 106.3(8) . . ?
C6 C10 Fe1 70.7(5) . . ?
C9 C10 Fe1 68.4(4) . . ?
C6 C10 H10 126.8 . . ?
C9 C10 H10 126.8 . . ?
Fe1 C10 H10 126.8 . . ?
C1 C11 N1 111.7(6) . . ?
C1 C11 H11A 109.3 . . ?
N1 C11 H11A 109.3 . . ?
C1 C11 H11B 109.3 . . ?
N1 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 N1 106.8(7) . . ?
C13 C12 H12 126.6 . . ?
N1 C12 H12 126.6 . . ?
C12 C13 N2 106.5(7) . . ?
C12 C13 H13 126.8 . . ?
N2 C13 H13 126.8 . . ?
N1 C14 N2 108.0(7) . . ?
N1 C14 H14 126.0 . . ?
N2 C14 H14 126.0 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 C17 125.1(7) . . ?
O1 C16 C21 121.8(7) . . ?
C17 C16 C21 113.0(6) . . ?
C18 C17 N3 117.1(7) . . ?
C18 C17 C16 122.6(7) . . ?
N3 C17 C16 120.3(7) . . ?
C19 C18 C17 120.3(7) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.7(7) . . ?
C18 C19 N4 120.7(7) . . ?
C20 C19 N4 117.6(7) . . ?
C21 C20 C19 118.6(6) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C16 123.6(6) . . ?
C20 C21 N5 119.7(6) . . ?
C16 C21 N5 116.6(6) . . ?
C14 N1 C12 109.4(6) . . ?
C14 N1 C11 125.5(7) . . ?
C12 N1 C11 125.1(6) . . ?
C14 N2 C13 109.3(6) . . ?
C14 N2 C15 125.4(7) . . ?
C13 N2 C15 125.3(7) . . ?
O2 N3 O3 121.2(8) . . ?
O2 N3 C17 120.4(8) . . ?
O3 N3 C17 118.5(8) . . ?
O5 N4 O4 123.3(7) . . ?
O5 N4 C19 119.9(7) . . ?
O4 N4 C19 116.8(7) . . ?
O7 N5 O6 121.1(8) . . ?
O7 N5 C21 118.6(7) . . ?
O6 N5 C21 120.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.732
_refine_diff_density_min         -1.440
_refine_diff_density_rms         0.083
_database_code_depnum_ccdc_archive 'CCDC 1001648'
#######################################################################
#
#                 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_exp_5986

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 Fe N5 O7'
_chemical_formula_weight         523.29

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.4141(4)
_cell_length_b                   11.4937(5)
_cell_length_c                   11.5265(6)
_cell_angle_alpha                109.571(4)
_cell_angle_beta                 96.214(4)
_cell_angle_gamma                105.601(4)
_cell_volume                     1104.50(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8909
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            22052
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4341
_reflns_number_gt                3681
_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)+(0.0552P)²+0.4729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4341
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.79994(3) 0.57992(3) 0.65110(3) 0.03795(13) Uani 1 1 d . . .
C1 C 0.6396(3) 0.0035(2) 0.8966(2) 0.0416(5) Uani 1 1 d . . .
C2 C 0.5070(3) -0.1050(2) 0.8170(2) 0.0403(5) Uani 1 1 d . . .
C3 C 0.4187(3) -0.1039(2) 0.7152(2) 0.0413(5) Uani 1 1 d . . .
H3 H 0.3344 -0.1760 0.6677 0.050 Uiso 1 1 calc R . .
C4 C 0.4544(2) 0.0036(2) 0.6832(2) 0.0392(5) Uani 1 1 d . . .
C5 C 0.5821(3) 0.1110(2) 0.7502(2) 0.0402(5) Uani 1 1 d . . .
H5A H 0.6063 0.1832 0.7276 0.048 Uiso 1 1 calc R . .
C6 C 0.6705(3) 0.1081(2) 0.8492(2) 0.0404(5) Uani 1 1 d . . .
C7 C 0.8936(3) 0.7665(2) 0.6663(2) 0.0392(5) Uani 1 1 d . . .
C8 C 0.9688(3) 0.6853(2) 0.5947(2) 0.0438(5) Uani 1 1 d . . .
H8 H 1.0763 0.6956 0.6159 0.053 Uiso 1 1 calc R . .
C9 C 0.8616(3) 0.5868(3) 0.4882(2) 0.0509(6) Uani 1 1 d . . .
H9 H 0.8818 0.5164 0.4232 0.061 Uiso 1 1 calc R . .
C10 C 0.7198(3) 0.6051(3) 0.4928(2) 0.0531(7) Uani 1 1 d . . .
H10 H 0.6247 0.5503 0.4314 0.064 Uiso 1 1 calc R . .
C11 C 0.7392(3) 0.7168(3) 0.6023(2) 0.0466(6) Uani 1 1 d . . .
H11 H 0.6598 0.7528 0.6296 0.056 Uiso 1 1 calc R . .
C12 C 0.8960(3) 0.5214(3) 0.7795(3) 0.0634(8) Uani 1 1 d . . .
H12 H 1.0042 0.5477 0.8154 0.076 Uiso 1 1 calc R . .
C13 C 0.8127(3) 0.4117(3) 0.6687(3) 0.0584(7) Uani 1 1 d . . .
H13 H 0.8532 0.3488 0.6141 0.070 Uiso 1 1 calc R . .
C14 C 0.6612(3) 0.4088(3) 0.6514(3) 0.0553(7) Uani 1 1 d . . .
H14 H 0.5777 0.3438 0.5823 0.066 Uiso 1 1 calc R . .
C15 C 0.6509(3) 0.5163(3) 0.7506(3) 0.0566(7) Uani 1 1 d . . .
H15 H 0.5591 0.5390 0.7632 0.068 Uiso 1 1 calc R . .
C16 C 0.7959(3) 0.5847(3) 0.8286(3) 0.0597(7) Uani 1 1 d . . .
H16 H 0.8224 0.6638 0.9051 0.072 Uiso 1 1 calc R . .
C17 C 0.9643(3) 0.8830(2) 0.7864(2) 0.0452(6) Uani 1 1 d . . .
H17A H 0.8879 0.8980 0.8343 0.054 Uiso 1 1 calc R . .
H17B H 1.0405 0.8670 0.8369 0.054 Uiso 1 1 calc R . .
C18 C 0.9726(3) 1.0359(2) 0.6688(2) 0.0519(7) Uani 1 1 d . . .
H18 H 0.8811 0.9891 0.6108 0.062 Uiso 1 1 calc R . .
C19 C 1.0679(3) 1.1499(3) 0.6795(2) 0.0556(7) Uani 1 1 d . . .
H19 H 1.0546 1.1975 0.6303 0.067 Uiso 1 1 calc R . .
C20 C 1.1655(3) 1.0920(2) 0.8232(2) 0.0405(5) Uani 1 1 d . . .
H20 H 1.2301 1.0916 0.8900 0.049 Uiso 1 1 calc R . .
C21 C 1.3207(3) 1.3042(3) 0.8217(3) 0.0590(7) Uani 1 1 d . . .
H21A H 1.3734 1.3057 0.7541 0.071 Uiso 1 1 calc R . .
H21B H 1.3897 1.3041 0.8904 0.071 Uiso 1 1 calc R . .
C22 C 1.2749(4) 1.4244(3) 0.8664(3) 0.0715(9) Uani 1 1 d . . .
H22A H 1.2186 1.4314 0.7959 0.107 Uiso 1 1 calc R . .
H22B H 1.3635 1.5000 0.9054 0.107 Uiso 1 1 calc R . .
H22C H 1.2131 1.4186 0.9266 0.107 Uiso 1 1 calc R . .
O1 O 0.7169(2) 0.0113(2) 0.99382(19) 0.0697(6) Uani 1 1 d . . .
O2 O 0.5313(3) -0.2310(2) 0.9326(2) 0.0892(8) Uani 1 1 d . . .
O3 O 0.3501(4) -0.3113(3) 0.7755(3) 0.1223(13) Uani 1 1 d . . .
O4 O 0.2454(2) -0.0928(2) 0.5202(2) 0.0751(7) Uani 1 1 d . . .
O5 O 0.3906(2) 0.09897(19) 0.54774(18) 0.0617(5) Uani 1 1 d . . .
O6 O 0.7984(3) 0.3279(2) 0.9361(3) 0.1040(10) Uani 1 1 d . . .
O7 O 0.9225(3) 0.1998(2) 0.9451(2) 0.0877(8) Uani 1 1 d . . .
N1 N 0.4601(3) -0.2221(2) 0.8444(2) 0.0586(6) Uani 1 1 d . . .
N2 N 0.3579(2) 0.0030(2) 0.5770(2) 0.0482(5) Uani 1 1 d . . .
N3 N 0.8066(3) 0.2206(2) 0.9162(2) 0.0538(6) Uani 1 1 d . . .
N4 N 1.0346(2) 1.00022(18) 0.75926(17) 0.0414(5) Uani 1 1 d . . .
N5 N 1.1892(2) 1.18457(19) 0.77602(19) 0.0456(5) Uani 1 1 d . . .


_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 C7 2.025(2) . ?
Fe1 C11 2.031(2) . ?
Fe1 C8 2.033(2) . ?
Fe1 C16 2.033(3) . ?
Fe1 C10 2.038(2) . ?
Fe1 C12 2.041(3) . ?
Fe1 C13 2.043(3) . ?
Fe1 C15 2.044(3) . ?
Fe1 C9 2.045(3) . ?
Fe1 C14 2.048(3) . ?
C1 O1 1.231(3) . ?
C1 C2 1.451(3) . ?
C1 C6 1.454(3) . ?
C2 C3 1.369(3) . ?
C2 N1 1.450(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 N2 1.440(3) . ?
C5 C6 1.353(3) . ?
C5 H5A 0.9300 . ?
C6 N3 1.462(3) . ?
C7 C8 1.421(3) . ?
C7 C11 1.422(3) . ?
C7 C17 1.494(3) . ?
C8 C9 1.412(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.409(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.419(4) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C12 C16 1.395(5) . ?
C12 C13 1.417(4) . ?
C12 H12 0.9800 . ?
C13 C14 1.408(4) . ?
C13 H13 0.9800 . ?
C14 C15 1.408(4) . ?
C14 H14 0.9800 . ?
C15 C16 1.404(4) . ?
C15 H15 0.9800 . ?
C16 H16 0.9800 . ?
C17 N4 1.483(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.331(4) . ?
C18 N4 1.370(3) . ?
C18 H18 0.9300 . ?
C19 N5 1.373(3) . ?
C19 H19 0.9300 . ?
C20 N4 1.326(3) . ?
C20 N5 1.328(3) . ?
C20 H20 0.9300 . ?
C21 N5 1.470(3) . ?
C21 C22 1.500(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O2 N1 1.204(3) . ?
O3 N1 1.208(3) . ?
O4 N2 1.226(3) . ?
O5 N2 1.231(3) . ?
O6 N3 1.202(3) . ?
O7 N3 1.215(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
C7 Fe1 C11 41.04(10) . . ?
C7 Fe1 C8 40.99(10) . . ?
C11 Fe1 C8 68.65(10) . . ?
C7 Fe1 C16 107.16(11) . . ?
C11 Fe1 C16 118.37(12) . . ?
C8 Fe1 C16 127.36(11) . . ?
C7 Fe1 C10 68.96(10) . . ?
C11 Fe1 C10 40.81(10) . . ?
C8 Fe1 C10 68.44(11) . . ?
C16 Fe1 C10 152.61(13) . . ?
C7 Fe1 C12 117.82(11) . . ?
C11 Fe1 C12 151.82(12) . . ?
C8 Fe1 C12 108.04(11) . . ?
C16 Fe1 C12 40.04(13) . . ?
C10 Fe1 C12 166.16(13) . . ?
C7 Fe1 C13 152.42(11) . . ?
C11 Fe1 C13 165.80(11) . . ?
C8 Fe1 C13 119.19(11) . . ?
C16 Fe1 C13 67.67(13) . . ?
C10 Fe1 C13 128.31(12) . . ?
C12 Fe1 C13 40.61(12) . . ?
C7 Fe1 C15 126.89(11) . . ?
C11 Fe1 C15 107.82(12) . . ?
C8 Fe1 C15 164.98(11) . . ?
C16 Fe1 C15 40.30(11) . . ?
C10 Fe1 C15 119.11(12) . . ?
C12 Fe1 C15 67.74(12) . . ?
C13 Fe1 C15 67.74(12) . . ?
C7 Fe1 C9 68.61(10) . . ?
C11 Fe1 C9 68.23(11) . . ?
C8 Fe1 C9 40.53(10) . . ?
C16 Fe1 C9 165.47(12) . . ?
C10 Fe1 C9 40.39(11) . . ?
C12 Fe1 C9 128.45(13) . . ?
C13 Fe1 C9 109.23(11) . . ?
C15 Fe1 C9 153.19(12) . . ?
C7 Fe1 C14 165.10(11) . . ?
C11 Fe1 C14 127.79(11) . . ?
C8 Fe1 C14 153.17(11) . . ?
C16 Fe1 C14 67.64(11) . . ?
C10 Fe1 C14 108.80(11) . . ?
C12 Fe1 C14 67.90(11) . . ?
C13 Fe1 C14 40.26(12) . . ?
C15 Fe1 C14 40.26(12) . . ?
C9 Fe1 C14 119.90(11) . . ?
O1 C1 C2 126.2(2) . . ?
O1 C1 C6 122.6(2) . . ?
C2 C1 C6 111.23(19) . . ?
C3 C2 N1 116.3(2) . . ?
C3 C2 C1 123.5(2) . . ?
N1 C2 C1 120.2(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 N2 118.8(2) . . ?
C5 C4 N2 120.0(2) . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 H5A 120.8 . . ?
C4 C5 H5A 120.8 . . ?
C5 C6 C1 125.4(2) . . ?
C5 C6 N3 117.5(2) . . ?
C1 C6 N3 117.1(2) . . ?
C8 C7 C11 107.4(2) . . ?
C8 C7 C17 126.2(2) . . ?
C11 C7 C17 126.4(2) . . ?
C8 C7 Fe1 69.78(13) . . ?
C11 C7 Fe1 69.69(14) . . ?
C17 C7 Fe1 126.10(16) . . ?
C9 C8 C7 108.1(2) . . ?
C9 C8 Fe1 70.18(14) . . ?
C7 C8 Fe1 69.22(13) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
Fe1 C8 H8 125.9 . . ?
C10 C9 C8 108.5(2) . . ?
C10 C9 Fe1 69.55(15) . . ?
C8 C9 Fe1 69.29(14) . . ?
C10 C9 H9 125.8 . . ?
C8 C9 H9 125.8 . . ?
Fe1 C9 H9 125.8 . . ?
C9 C10 C11 107.9(2) . . ?
C9 C10 Fe1 70.05(14) . . ?
C11 C10 Fe1 69.33(14) . . ?
C9 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
Fe1 C10 H10 126.1 . . ?
C10 C11 C7 108.1(2) . . ?
C10 C11 Fe1 69.86(14) . . ?
C7 C11 Fe1 69.27(13) . . ?
C10 C11 H11 125.9 . . ?
C7 C11 H11 125.9 . . ?
Fe1 C11 H11 125.9 . . ?
C16 C12 C13 107.6(3) . . ?
C16 C12 Fe1 69.68(16) . . ?
C13 C12 Fe1 69.79(15) . . ?
C16 C12 H12 126.2 . . ?
C13 C12 H12 126.2 . . ?
Fe1 C12 H12 126.2 . . ?
C14 C13 C12 107.9(3) . . ?
C14 C13 Fe1 70.07(15) . . ?
C12 C13 Fe1 69.60(16) . . ?
C14 C13 H13 126.1 . . ?
C12 C13 H13 126.1 . . ?
Fe1 C13 H13 126.1 . . ?
C13 C14 C15 107.9(3) . . ?
C13 C14 Fe1 69.67(15) . . ?
C15 C14 Fe1 69.69(15) . . ?
C13 C14 H14 126.0 . . ?
C15 C14 H14 126.0 . . ?
Fe1 C14 H14 126.0 . . ?
C16 C15 C14 107.7(3) . . ?
C16 C15 Fe1 69.43(16) . . ?
C14 C15 Fe1 70.05(16) . . ?
C16 C15 H15 126.1 . . ?
C14 C15 H15 126.1 . . ?
Fe1 C15 H15 126.1 . . ?
C12 C16 C15 108.8(3) . . ?
C12 C16 Fe1 70.28(16) . . ?
C15 C16 Fe1 70.27(15) . . ?
C12 C16 H16 125.6 . . ?
C15 C16 H16 125.6 . . ?
Fe1 C16 H16 125.6 . . ?
N4 C17 C7 110.39(19) . . ?
N4 C17 H17A 109.6 . . ?
C7 C17 H17A 109.6 . . ?
N4 C17 H17B 109.6 . . ?
C7 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 N4 107.3(2) . . ?
C19 C18 H18 126.4 . . ?
N4 C18 H18 126.4 . . ?
C18 C19 N5 107.7(2) . . ?
C18 C19 H19 126.1 . . ?
N5 C19 H19 126.1 . . ?
N4 C20 N5 108.7(2) . . ?
N4 C20 H20 125.6 . . ?
N5 C20 H20 125.6 . . ?
N5 C21 C22 111.6(3) . . ?
N5 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N5 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 N1 O3 120.9(3) . . ?
O2 N1 C2 120.6(2) . . ?
O3 N1 C2 118.6(2) . . ?
O4 N2 O5 122.7(2) . . ?
O4 N2 C4 118.5(2) . . ?
O5 N2 C4 118.8(2) . . ?
O6 N3 O7 123.9(3) . . ?
O6 N3 C6 118.2(2) . . ?
O7 N3 C6 117.8(2) . . ?
C20 N4 C18 108.3(2) . . ?
C20 N4 C17 125.41(19) . . ?
C18 N4 C17 126.2(2) . . ?
C20 N5 C19 107.9(2) . . ?
C20 N5 C21 125.7(2) . . ?
C19 N5 C21 126.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 973759'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 Fe N5 O7'
_chemical_formula_weight         537.31

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.4108(3)
_cell_length_b                   13.2305(6)
_cell_length_c                   13.7738(5)
_cell_angle_alpha                63.098(4)
_cell_angle_beta                 74.466(3)
_cell_angle_gamma                78.581(4)
_cell_volume                     1155.71(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_T_max  0.9261
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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            23135
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4524
_reflns_number_gt                3992
_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)+(0.0415P)²+0.4551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4524
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.13615(4) 0.17202(2) 0.29021(2) 0.03497(10) Uani 1 1 d . . .
N1 N 0.2477(2) -0.04087(15) 0.10754(13) 0.0439(4) Uani 1 1 d . . .
N2 N 0.1719(2) -0.16221(14) 0.06518(13) 0.0413(4) Uani 1 1 d . . .
N3 N 0.6224(4) 0.81027(16) 0.3650(2) 0.0658(6) Uani 1 1 d . . .
N4 N 0.7948(2) 0.41191(15) 0.58351(13) 0.0452(4) Uani 1 1 d . . .
N5 N 0.6770(2) 0.52348(15) 0.21829(14) 0.0474(4) Uani 1 1 d . . .
C1 C 0.1438(3) 0.09831(16) 0.18869(15) 0.0378(4) Uani 1 1 d . . .
C2 C 0.1516(4) 0.2177(2) 0.12714(17) 0.0564(6) Uani 1 1 d . . .
H2 H 0.2539 0.2557 0.0661 0.068 Uiso 1 1 calc R . .
C3 C -0.0108(4) 0.2721(2) 0.1692(2) 0.0674(7) Uani 1 1 d . . .
H3 H -0.0412 0.3546 0.1430 0.081 Uiso 1 1 calc R . .
C4 C -0.1211(3) 0.1890(3) 0.2551(2) 0.0661(7) Uani 1 1 d . . .
H4 H -0.2420 0.2030 0.2999 0.079 Uiso 1 1 calc R . .
C5 C -0.0285(3) 0.08149(19) 0.26782(17) 0.0467(5) Uani 1 1 d . . .
H5 H -0.0740 0.0079 0.3225 0.056 Uiso 1 1 calc R . .
C6 C 0.3771(3) 0.11779(19) 0.35201(19) 0.0492(5) Uani 1 1 d . . .
H6 H 0.4851 0.0712 0.3297 0.059 Uiso 1 1 calc R . .
C7 C 0.3508(3) 0.23809(19) 0.30251(19) 0.0511(5) Uani 1 1 d . . .
H7 H 0.4376 0.2894 0.2403 0.061 Uiso 1 1 calc R . .
C8 C 0.1786(3) 0.27094(19) 0.35873(19) 0.0529(5) Uani 1 1 d . . .
H8 H 0.1242 0.3493 0.3427 0.064 Uiso 1 1 calc R . .
C9 C 0.0980(3) 0.1715(2) 0.44248(18) 0.0548(5) Uani 1 1 d . . .
H9 H -0.0223 0.1685 0.4949 0.066 Uiso 1 1 calc R . .
C10 C 0.2218(3) 0.07698(18) 0.43783(17) 0.0510(5) Uani 1 1 d . . .
H10 H 0.2021 -0.0032 0.4862 0.061 Uiso 1 1 calc R . .
C11 C 0.2881(3) 0.0078(2) 0.1766(2) 0.0596(6) Uani 1 1 d . . .
H11A H 0.2960 -0.0524 0.2498 0.071 Uiso 1 1 calc R . .
H11B H 0.4093 0.0389 0.1431 0.071 Uiso 1 1 calc R . .
C12 C 0.1956(3) -0.14418(18) 0.14733(16) 0.0455(5) Uani 1 1 d . . .
H12 H 0.1783 -0.1962 0.2216 0.055 Uiso 1 1 calc R . .
C13 C 0.2119(3) -0.06648(18) -0.03162(15) 0.0441(5) Uani 1 1 d . . .
H13 H 0.2071 -0.0561 -0.1024 0.053 Uiso 1 1 calc R . .
C14 C 0.2594(3) 0.00949(18) -0.00542(17) 0.0459(5) Uani 1 1 d . . .
H14 H 0.2936 0.0823 -0.0544 0.055 Uiso 1 1 calc R . .
C15 C 0.1219(3) -0.27032(19) 0.0782(2) 0.0538(5) Uani 1 1 d . . .
H15A H 0.0296 -0.2547 0.0337 0.065 Uiso 1 1 calc R . .
H15B H 0.0650 -0.3136 0.1554 0.065 Uiso 1 1 calc R . .
C16 C 0.2876(4) -0.3397(2) 0.0441(2) 0.0694(7) Uani 1 1 d . . .
H16A H 0.3863 -0.3478 0.0820 0.083 Uiso 1 1 calc R . .
H16B H 0.3353 -0.3009 -0.0353 0.083 Uiso 1 1 calc R . .
C17 C 0.2370(5) -0.4565(2) 0.0716(3) 0.0891(9) Uani 1 1 d . . .
H17A H 0.3462 -0.4992 0.0481 0.134 Uiso 1 1 calc R . .
H17B H 0.1401 -0.4487 0.0336 0.134 Uiso 1 1 calc R . .
H17C H 0.1927 -0.4958 0.1503 0.134 Uiso 1 1 calc R . .
C18 C 0.6478(3) 0.67641(15) 0.28122(15) 0.0404(4) Uani 1 1 d . . .
C19 C 0.6637(3) 0.69374(16) 0.37509(17) 0.0432(4) Uani 1 1 d . . .
C20 C 0.7058(3) 0.61149(16) 0.47237(16) 0.0412(4) Uani 1 1 d . . .
H20A H 0.7089 0.6292 0.5299 0.049 Uiso 1 1 calc R . .
C21 C 0.7441(2) 0.50007(15) 0.48335(14) 0.0362(4) Uani 1 1 d . . .
C22 C 0.7319(2) 0.47300(15) 0.39960(14) 0.0365(4) Uani 1 1 d . . .
H22 H 0.7528 0.3978 0.4090 0.044 Uiso 1 1 calc R . .
C23 C 0.6886(3) 0.55767(16) 0.30282(14) 0.0370(4) Uani 1 1 d . . .
O1 O 0.5958(2) 0.75300(13) 0.19688(12) 0.0600(4) Uani 1 1 d . . .
O2 O 0.7082(4) 0.88388(16) 0.2850(2) 0.1046(8) Uani 1 1 d . . .
O3 O 0.5037(4) 0.82706(18) 0.4374(2) 0.1075(8) Uani 1 1 d . . .
O4 O 0.8048(3) 0.43689(15) 0.65715(13) 0.0663(5) Uani 1 1 d . . .
O5 O 0.8272(3) 0.31371(13) 0.59191(12) 0.0652(5) Uani 1 1 d . . .
O6 O 0.6117(3) 0.43465(15) 0.24806(15) 0.0760(5) Uani 1 1 d . . .
O7 O 0.7358(3) 0.58405(18) 0.12158(13) 0.0844(6) Uani 1 1 d . . .


_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 C1 2.0197(18) . ?
Fe1 C2 2.021(2) . ?
Fe1 C3 2.030(2) . ?
Fe1 C5 2.0331(19) . ?
Fe1 C8 2.035(2) . ?
Fe1 C4 2.036(2) . ?
Fe1 C9 2.037(2) . ?
Fe1 C7 2.037(2) . ?
Fe1 C10 2.045(2) . ?
Fe1 C6 2.045(2) . ?
N1 C12 1.317(3) . ?
N1 C14 1.373(3) . ?
N1 C11 1.481(3) . ?
N2 C12 1.317(2) . ?
N2 C13 1.371(2) . ?
N2 C15 1.469(3) . ?
N3 O2 1.211(3) . ?
N3 O3 1.213(3) . ?
N3 C19 1.460(3) . ?
N4 O4 1.224(2) . ?
N4 O5 1.231(2) . ?
N4 C21 1.433(2) . ?
N5 O6 1.211(2) . ?
N5 O7 1.212(2) . ?
N5 C23 1.454(2) . ?
C1 C2 1.420(3) . ?
C1 C5 1.420(3) . ?
C1 C11 1.477(3) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.406(3) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C10 1.397(3) . ?
C6 C7 1.415(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.404(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.410(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.413(3) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C13 C14 1.342(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.485(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.515(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O1 1.243(2) . ?
C18 C23 1.444(3) . ?
C18 C19 1.449(3) . ?
C19 C20 1.359(3) . ?
C20 C21 1.390(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.382(3) . ?
C22 C23 1.367(2) . ?
C22 H22 0.9300 . ?

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
C1 Fe1 C2 41.14(8) . . ?
C1 Fe1 C3 68.81(9) . . ?
C2 Fe1 C3 40.48(11) . . ?
C1 Fe1 C5 41.02(8) . . ?
C2 Fe1 C5 68.40(9) . . ?
C3 Fe1 C5 67.97(10) . . ?
C1 Fe1 C8 165.08(9) . . ?
C2 Fe1 C8 126.68(9) . . ?
C3 Fe1 C8 107.16(9) . . ?
C5 Fe1 C8 152.25(9) . . ?
C1 Fe1 C4 68.64(8) . . ?
C2 Fe1 C4 67.85(11) . . ?
C3 Fe1 C4 40.04(11) . . ?
C5 Fe1 C4 40.43(10) . . ?
C8 Fe1 C4 118.16(10) . . ?
C1 Fe1 C9 153.17(9) . . ?
C2 Fe1 C9 164.47(10) . . ?
C3 Fe1 C9 127.06(11) . . ?
C5 Fe1 C9 119.23(9) . . ?
C8 Fe1 C9 40.51(9) . . ?
C4 Fe1 C9 108.36(10) . . ?
C1 Fe1 C7 127.71(9) . . ?
C2 Fe1 C7 107.71(9) . . ?
C3 Fe1 C7 118.05(10) . . ?
C5 Fe1 C7 166.57(9) . . ?
C8 Fe1 C7 40.34(9) . . ?
C4 Fe1 C7 151.45(11) . . ?
C9 Fe1 C7 67.96(9) . . ?
C1 Fe1 C10 119.38(8) . . ?
C2 Fe1 C10 153.33(10) . . ?
C3 Fe1 C10 165.45(11) . . ?
C5 Fe1 C10 109.48(9) . . ?
C8 Fe1 C10 68.01(9) . . ?
C4 Fe1 C10 128.86(11) . . ?
C9 Fe1 C10 40.52(9) . . ?
C7 Fe1 C10 67.83(9) . . ?
C1 Fe1 C6 108.63(8) . . ?
C2 Fe1 C6 119.40(10) . . ?
C3 Fe1 C6 152.57(11) . . ?
C5 Fe1 C6 129.05(9) . . ?
C8 Fe1 C6 67.92(9) . . ?
C4 Fe1 C6 166.54(11) . . ?
C9 Fe1 C6 67.75(9) . . ?
C7 Fe1 C6 40.57(9) . . ?
C10 Fe1 C6 39.96(9) . . ?
C12 N1 C14 108.37(17) . . ?
C12 N1 C11 123.91(18) . . ?
C14 N1 C11 127.72(19) . . ?
C12 N2 C13 108.22(17) . . ?
C12 N2 C15 124.19(17) . . ?
C13 N2 C15 127.50(17) . . ?
O2 N3 O3 124.2(2) . . ?
O2 N3 C19 118.1(2) . . ?
O3 N3 C19 117.7(2) . . ?
O4 N4 O5 122.49(17) . . ?
O4 N4 C21 118.99(18) . . ?
O5 N4 C21 118.51(17) . . ?
O6 N5 O7 123.03(19) . . ?
O6 N5 C23 118.35(17) . . ?
O7 N5 C23 118.61(18) . . ?
C2 C1 C5 106.73(19) . . ?
C2 C1 C11 127.3(2) . . ?
C5 C1 C11 125.9(2) . . ?
C2 C1 Fe1 69.48(11) . . ?
C5 C1 Fe1 70.00(11) . . ?
C11 C1 Fe1 124.01(13) . . ?
C3 C2 C1 108.4(2) . . ?
C3 C2 Fe1 70.11(13) . . ?
C1 C2 Fe1 69.38(11) . . ?
C3 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
Fe1 C2 H2 125.8 . . ?
C4 C3 C2 108.3(2) . . ?
C4 C3 Fe1 70.20(14) . . ?
C2 C3 Fe1 69.41(13) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C3 C4 C5 108.5(2) . . ?
C3 C4 Fe1 69.76(13) . . ?
C5 C4 Fe1 69.68(12) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe1 C4 H4 125.7 . . ?
C4 C5 C1 108.0(2) . . ?
C4 C5 Fe1 69.89(12) . . ?
C1 C5 Fe1 68.98(10) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C10 C6 C7 108.2(2) . . ?
C10 C6 Fe1 70.01(12) . . ?
C7 C6 Fe1 69.44(12) . . ?
C10 C6 H6 125.9 . . ?
C7 C6 H6 125.9 . . ?
Fe1 C6 H6 125.9 . . ?
C8 C7 C6 107.9(2) . . ?
C8 C7 Fe1 69.75(12) . . ?
C6 C7 Fe1 70.00(11) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 126.1 . . ?
C7 C8 C9 108.0(2) . . ?
C7 C8 Fe1 69.91(12) . . ?
C9 C8 Fe1 69.81(12) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
Fe1 C8 H8 126.0 . . ?
C8 C9 C10 107.9(2) . . ?
C8 C9 Fe1 69.68(12) . . ?
C10 C9 Fe1 70.03(12) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
Fe1 C9 H9 126.1 . . ?
C6 C10 C9 108.08(19) . . ?
C6 C10 Fe1 70.03(12) . . ?
C9 C10 Fe1 69.45(12) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
C1 C11 N1 112.83(17) . . ?
C1 C11 H11A 109.0 . . ?
N1 C11 H11A 109.0 . . ?
C1 C11 H11B 109.0 . . ?
N1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 N2 109.23(17) . . ?
N1 C12 H12 125.4 . . ?
N2 C12 H12 125.4 . . ?
C14 C13 N2 107.30(17) . . ?
C14 C13 H13 126.3 . . ?
N2 C13 H13 126.3 . . ?
C13 C14 N1 106.88(18) . . ?
C13 C14 H14 126.6 . . ?
N1 C14 H14 126.6 . . ?
N2 C15 C16 112.35(19) . . ?
N2 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.3(2) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 C23 125.26(18) . . ?
O1 C18 C19 124.00(18) . . ?
C23 C18 C19 110.63(15) . . ?
C20 C19 C18 126.14(18) . . ?
C20 C19 N3 117.51(19) . . ?
C18 C19 N3 116.29(17) . . ?
C19 C20 C21 118.09(18) . . ?
C19 C20 H20A 121.0 . . ?
C21 C20 H20A 121.0 . . ?
C22 C21 C20 120.94(16) . . ?
C22 C21 N4 119.59(17) . . ?
C20 C21 N4 119.47(17) . . ?
C23 C22 C21 119.51(17) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C18 124.62(17) . . ?
C22 C23 N5 116.78(17) . . ?
C18 C23 N5 118.56(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 973760'
#######################################################################
#
#                 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_exp_5982

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 Fe N5 O7'
_chemical_formula_weight         537.31

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.0568(4)
_cell_length_b                   11.2915(4)
_cell_length_c                   11.3242(4)
_cell_angle_alpha                77.032(3)
_cell_angle_beta                 73.612(3)
_cell_angle_gamma                62.236(4)
_cell_volume                     1192.99(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9040
_exptl_absorpt_correction_T_max  0.9283
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            24002
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4676
_reflns_number_gt                3929
_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)+(0.0614P)²+0.8412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4676
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 -0.02895(4) 0.27937(4) 0.41209(3) 0.04717(14) Uani 1 1 d . . .
C1 C 0.4214(3) 0.3732(3) 0.9747(2) 0.0448(6) Uani 1 1 d . . .
C2 C 0.5260(3) 0.3455(2) 0.8603(2) 0.0442(5) Uani 1 1 d . . .
C3 C 0.5456(3) 0.4434(3) 0.7716(2) 0.0475(6) Uani 1 1 d . . .
H3 H 0.6161 0.4197 0.7012 0.057 Uiso 1 1 calc R . .
C4 C 0.4606(3) 0.5768(2) 0.7871(2) 0.0448(6) Uani 1 1 d . . .
C5 C 0.3523(3) 0.6140(3) 0.8890(2) 0.0453(6) Uani 1 1 d . . .
H5 H 0.2936 0.7045 0.8973 0.054 Uiso 1 1 calc R . .
C6 C 0.3324(3) 0.5171(3) 0.9771(2) 0.0451(6) Uani 1 1 d . . .
C7 C 0.1793(2) 0.1705(2) 0.3996(2) 0.0418(5) Uani 1 1 d . . .
C8 C 0.1343(3) 0.2948(3) 0.4456(3) 0.0591(7) Uani 1 1 d . . .
H8 H 0.1667 0.3647 0.4073 0.071 Uiso 1 1 calc R . .
C9 C 0.0335(3) 0.2997(4) 0.5566(3) 0.0754(10) Uani 1 1 d . . .
H9 H -0.0169 0.3745 0.6080 0.090 Uiso 1 1 calc R . .
C10 C 0.0169(3) 0.1807(4) 0.5797(3) 0.0752(10) Uani 1 1 d . . .
H10 H -0.0472 0.1579 0.6499 0.090 Uiso 1 1 calc R . .
C11 C 0.1061(3) 0.0999(3) 0.4834(3) 0.0551(7) Uani 1 1 d . . .
H11 H 0.1158 0.0110 0.4758 0.066 Uiso 1 1 calc R . .
C12 C -0.0664(4) 0.3227(7) 0.2405(3) 0.116(2) Uani 1 1 d . . .
H12 H 0.0029 0.3000 0.1631 0.140 Uiso 1 1 calc R . .
C13 C -0.1214(5) 0.4397(5) 0.2947(5) 0.1040(16) Uani 1 1 d . . .
H13 H -0.0958 0.5149 0.2634 0.125 Uiso 1 1 calc R . .
C14 C -0.2173(4) 0.4345(5) 0.3952(5) 0.0970(14) Uani 1 1 d . . .
H14 H -0.2712 0.5051 0.4510 0.116 Uiso 1 1 calc R . .
C15 C -0.2272(4) 0.3186(6) 0.4115(4) 0.0884(13) Uani 1 1 d . . .
H15 H -0.2901 0.2914 0.4794 0.106 Uiso 1 1 calc R . .
C16 C -0.1347(5) 0.2435(4) 0.3174(5) 0.1022(16) Uani 1 1 d . . .
H16 H -0.1216 0.1554 0.3034 0.123 Uiso 1 1 calc R . .
C17 C 0.2765(3) 0.1259(3) 0.2806(2) 0.0477(6) Uani 1 1 d . . .
H17A H 0.2792 0.2042 0.2253 0.057 Uiso 1 1 calc R . .
H17B H 0.2409 0.0833 0.2423 0.057 Uiso 1 1 calc R . .
C18 C 0.4600(3) -0.0644(3) 0.3937(3) 0.0569(7) Uani 1 1 d . . .
H18 H 0.4012 -0.0754 0.4680 0.068 Uiso 1 1 calc R . .
C19 C 0.5978(3) -0.1381(3) 0.3636(3) 0.0579(7) Uani 1 1 d . . .
H19 H 0.6528 -0.2093 0.4130 0.070 Uiso 1 1 calc R . .
C20 C 0.5339(3) 0.0124(2) 0.2076(2) 0.0428(5) Uani 1 1 d . . .
H20 H 0.5362 0.0633 0.1308 0.051 Uiso 1 1 calc R . .
C21 C 0.7887(3) -0.1471(3) 0.1743(3) 0.0546(7) Uani 1 1 d . . .
H21 H 0.8471 -0.2120 0.2319 0.066 Uiso 1 1 calc R . .
C22 C 0.7980(4) -0.2245(4) 0.0774(4) 0.0880(12) Uani 1 1 d . . .
H22A H 0.7645 -0.2914 0.1163 0.132 Uiso 1 1 calc R . .
H22B H 0.8935 -0.2676 0.0351 0.132 Uiso 1 1 calc R . .
H22C H 0.7421 -0.1638 0.0191 0.132 Uiso 1 1 calc R . .
C23 C 0.8411(4) -0.0406(4) 0.1254(4) 0.0938(13) Uani 1 1 d . . .
H23A H 0.7901 0.0219 0.0644 0.141 Uiso 1 1 calc R . .
H23B H 0.9387 -0.0820 0.0882 0.141 Uiso 1 1 calc R . .
H23C H 0.8280 0.0064 0.1922 0.141 Uiso 1 1 calc R . .
O1 O 0.4104(2) 0.2882(2) 1.0606(2) 0.0727(6) Uani 1 1 d . . .
O2 O 0.6087(4) 0.1166(2) 0.9103(3) 0.1254(14) Uani 1 1 d . . .
O3 O 0.7001(4) 0.1858(3) 0.7384(3) 0.1191(13) Uani 1 1 d . . .
O4 O 0.5798(3) 0.6455(3) 0.6072(2) 0.0962(9) Uani 1 1 d . . .
O5 O 0.4021(3) 0.7982(2) 0.7068(2) 0.0726(6) Uani 1 1 d . . .
O6 O 0.1632(3) 0.6784(3) 1.1001(3) 0.1204(12) Uani 1 1 d . . .
O7 O 0.1731(5) 0.4900(4) 1.1442(5) 0.206(3) Uani 1 1 d . . .
N1 N 0.6198(3) 0.2076(2) 0.8367(2) 0.0614(6) Uani 1 1 d . . .
N2 N 0.4819(3) 0.6801(3) 0.6950(2) 0.0587(6) Uani 1 1 d . . .
N3 N 0.2151(3) 0.5630(3) 1.0809(3) 0.0671(7) Uani 1 1 d . . .
N4 N 0.4208(2) 0.0300(2) 0.29581(18) 0.0417(4) Uani 1 1 d . . .
N5 N 0.6430(2) -0.0891(2) 0.24630(19) 0.0447(5) Uani 1 1 d . . .


_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 C16 2.006(4) . ?
Fe1 C12 2.007(3) . ?
Fe1 C13 2.013(4) . ?
Fe1 C7 2.022(2) . ?
Fe1 C15 2.026(3) . ?
Fe1 C11 2.029(3) . ?
Fe1 C14 2.030(4) . ?
Fe1 C8 2.035(3) . ?
Fe1 C9 2.040(3) . ?
Fe1 C10 2.042(3) . ?
C1 O1 1.226(3) . ?
C1 C2 1.454(4) . ?
C1 C6 1.458(4) . ?
C2 C3 1.371(3) . ?
C2 N1 1.449(3) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 N2 1.442(3) . ?
C5 C6 1.361(3) . ?
C5 H5 0.9300 . ?
C6 N3 1.456(3) . ?
C7 C11 1.421(4) . ?
C7 C8 1.422(4) . ?
C7 C17 1.486(3) . ?
C8 C9 1.417(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.399(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.412(5) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C12 C13 1.376(7) . ?
C12 C16 1.427(7) . ?
C12 H12 0.9800 . ?
C13 C14 1.331(7) . ?
C13 H13 0.9800 . ?
C14 C15 1.331(6) . ?
C14 H14 0.9800 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9800 . ?
C16 H16 0.9800 . ?
C17 N4 1.487(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.336(4) . ?
C18 N4 1.365(3) . ?
C18 H18 0.9300 . ?
C19 N5 1.368(3) . ?
C19 H19 0.9300 . ?
C20 N5 1.321(3) . ?
C20 N4 1.324(3) . ?
C20 H20 0.9300 . ?
C21 N5 1.485(3) . ?
C21 C23 1.502(5) . ?
C21 C22 1.504(4) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O2 N1 1.201(3) . ?
O3 N1 1.204(3) . ?
O4 N2 1.219(3) . ?
O5 N2 1.221(3) . ?
O6 N3 1.197(4) . ?
O7 N3 1.146(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
C16 Fe1 C12 41.7(2) . . ?
C16 Fe1 C13 67.7(2) . . ?
C12 Fe1 C13 40.0(2) . . ?
C16 Fe1 C7 121.97(16) . . ?
C12 Fe1 C7 107.84(13) . . ?
C13 Fe1 C7 125.74(17) . . ?
C16 Fe1 C15 39.80(19) . . ?
C12 Fe1 C15 67.41(16) . . ?
C13 Fe1 C15 65.64(18) . . ?
C7 Fe1 C15 157.65(18) . . ?
C16 Fe1 C11 108.25(16) . . ?
C12 Fe1 C11 125.9(2) . . ?
C13 Fe1 C11 163.0(2) . . ?
C7 Fe1 C11 41.07(10) . . ?
C15 Fe1 C11 122.66(17) . . ?
C16 Fe1 C14 65.95(19) . . ?
C12 Fe1 C14 65.97(18) . . ?
C13 Fe1 C14 38.44(19) . . ?
C7 Fe1 C14 161.62(19) . . ?
C15 Fe1 C14 38.33(19) . . ?
C11 Fe1 C14 156.66(19) . . ?
C16 Fe1 C8 157.5(2) . . ?
C12 Fe1 C8 120.79(19) . . ?
C13 Fe1 C8 108.22(17) . . ?
C7 Fe1 C8 41.02(11) . . ?
C15 Fe1 C8 160.59(18) . . ?
C11 Fe1 C8 68.75(12) . . ?
C14 Fe1 C8 125.56(18) . . ?
C16 Fe1 C9 160.8(2) . . ?
C12 Fe1 C9 155.7(3) . . ?
C13 Fe1 C9 121.2(2) . . ?
C7 Fe1 C9 68.63(11) . . ?
C15 Fe1 C9 124.92(16) . . ?
C11 Fe1 C9 68.16(14) . . ?
C14 Fe1 C9 109.37(16) . . ?
C8 Fe1 C9 40.69(14) . . ?
C16 Fe1 C10 125.0(2) . . ?
C12 Fe1 C10 163.0(3) . . ?
C13 Fe1 C10 155.3(2) . . ?
C7 Fe1 C10 68.60(11) . . ?
C15 Fe1 C10 109.16(15) . . ?
C11 Fe1 C10 40.60(13) . . ?
C14 Fe1 C10 122.46(17) . . ?
C8 Fe1 C10 68.19(14) . . ?
C9 Fe1 C10 40.08(16) . . ?
O1 C1 C2 125.2(2) . . ?
O1 C1 C6 123.5(2) . . ?
C2 C1 C6 111.3(2) . . ?
C3 C2 N1 116.2(2) . . ?
C3 C2 C1 123.9(2) . . ?
N1 C2 C1 119.9(2) . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 N2 119.9(2) . . ?
C5 C4 N2 119.1(2) . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 N3 116.6(2) . . ?
C5 C6 C1 124.4(2) . . ?
N3 C6 C1 118.9(2) . . ?
C11 C7 C8 107.6(2) . . ?
C11 C7 C17 125.6(2) . . ?
C8 C7 C17 126.6(2) . . ?
C11 C7 Fe1 69.71(15) . . ?
C8 C7 Fe1 69.98(15) . . ?
C17 C7 Fe1 122.13(17) . . ?
C9 C8 C7 107.6(3) . . ?
C9 C8 Fe1 69.84(18) . . ?
C7 C8 Fe1 69.00(15) . . ?
C9 C8 H8 126.2 . . ?
C7 C8 H8 126.2 . . ?
Fe1 C8 H8 126.2 . . ?
C10 C9 C8 108.5(3) . . ?
C10 C9 Fe1 70.01(19) . . ?
C8 C9 Fe1 69.46(17) . . ?
C10 C9 H9 125.7 . . ?
C8 C9 H9 125.7 . . ?
Fe1 C9 H9 125.7 . . ?
C9 C10 C11 108.4(3) . . ?
C9 C10 Fe1 69.91(19) . . ?
C11 C10 Fe1 69.21(16) . . ?
C9 C10 H10 125.8 . . ?
C11 C10 H10 125.8 . . ?
Fe1 C10 H10 125.8 . . ?
C10 C11 C7 107.9(3) . . ?
C10 C11 Fe1 70.19(17) . . ?
C7 C11 Fe1 69.23(14) . . ?
C10 C11 H11 126.1 . . ?
C7 C11 H11 126.1 . . ?
Fe1 C11 H11 126.1 . . ?
C13 C12 C16 106.1(4) . . ?
C13 C12 Fe1 70.2(2) . . ?
C16 C12 Fe1 69.1(2) . . ?
C13 C12 H12 126.9 . . ?
C16 C12 H12 126.9 . . ?
Fe1 C12 H12 126.9 . . ?
C14 C13 C12 108.5(5) . . ?
C14 C13 Fe1 71.4(2) . . ?
C12 C13 Fe1 69.7(2) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
Fe1 C13 H13 125.7 . . ?
C13 C14 C15 110.6(4) . . ?
C13 C14 Fe1 70.1(2) . . ?
C15 C14 Fe1 70.7(2) . . ?
C13 C14 H14 124.7 . . ?
C15 C14 H14 124.7 . . ?
Fe1 C14 H14 124.7 . . ?
C14 C15 C16 108.6(4) . . ?
C14 C15 Fe1 71.0(2) . . ?
C16 C15 Fe1 69.3(2) . . ?
C14 C15 H15 125.7 . . ?
C16 C15 H15 125.7 . . ?
Fe1 C15 H15 125.7 . . ?
C15 C16 C12 106.1(4) . . ?
C15 C16 Fe1 70.9(2) . . ?
C12 C16 Fe1 69.2(2) . . ?
C15 C16 H16 126.9 . . ?
C12 C16 H16 126.9 . . ?
Fe1 C16 H16 126.9 . . ?
C7 C17 N4 113.0(2) . . ?
C7 C17 H17A 109.0 . . ?
N4 C17 H17A 109.0 . . ?
C7 C17 H17B 109.0 . . ?
N4 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 N4 107.7(2) . . ?
C19 C18 H18 126.2 . . ?
N4 C18 H18 126.2 . . ?
C18 C19 N5 107.2(2) . . ?
C18 C19 H19 126.4 . . ?
N5 C19 H19 126.4 . . ?
N5 C20 N4 109.1(2) . . ?
N5 C20 H20 125.5 . . ?
N4 C20 H20 125.5 . . ?
N5 C21 C23 111.0(2) . . ?
N5 C21 C22 109.5(3) . . ?
C23 C21 C22 114.7(3) . . ?
N5 C21 H21 107.1 . . ?
C23 C21 H21 107.1 . . ?
C22 C21 H21 107.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 N1 O3 120.7(3) . . ?
O2 N1 C2 119.8(3) . . ?
O3 N1 C2 119.2(2) . . ?
O4 N2 O5 122.4(2) . . ?
O4 N2 C4 118.1(3) . . ?
O5 N2 C4 119.5(3) . . ?
O7 N3 O6 120.1(3) . . ?
O7 N3 C6 120.7(3) . . ?
O6 N3 C6 119.2(3) . . ?
C20 N4 C18 107.9(2) . . ?
C20 N4 C17 124.2(2) . . ?
C18 N4 C17 127.5(2) . . ?
C20 N5 C19 108.1(2) . . ?
C20 N5 C21 126.9(2) . . ?
C19 N5 C21 124.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 973761'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 Fe N5 O7'
_chemical_formula_weight         551.34

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   22.3748(9)
_cell_length_b                   5.7925(3)
_cell_length_c                   19.3420(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2506.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8911
_exptl_absorpt_correction_T_max  0.9314
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13298
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4775
_reflns_number_gt                3178
_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)+(0.0479P)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    constr
_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   -0.02(3)
_refine_ls_number_reflns         4775
_refine_ls_number_parameters     335
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.61762(3) 0.34542(10) 0.67450(5) 0.0562(2) Uani 1 1 d . . .
C1 C 0.7050(2) 0.3842(8) 0.6494(2) 0.0513(13) Uani 1 1 d . . .
C2 C 0.6801(2) 0.6016(7) 0.6661(4) 0.0659(14) Uani 1 1 d . . .
H2 H 0.6779 0.7364 0.6356 0.079 Uiso 1 1 calc R . .
C9 C 0.5360(3) 0.2221(17) 0.7005(4) 0.105(3) Uani 1 1 d . . .
H9 H 0.5217 0.1891 0.7473 0.126 Uiso 1 1 calc R . .
C5 C 0.6989(2) 0.2366(10) 0.7063(3) 0.0656(15) Uani 1 1 d . . .
H5 H 0.7125 0.0760 0.7091 0.079 Uiso 1 1 calc R . .
C4 C 0.6701(2) 0.3642(13) 0.7598(3) 0.0816(19) Uani 1 1 d . . .
H4 H 0.6601 0.3075 0.8061 0.098 Uiso 1 1 calc R . .
C11 C 0.7326(2) 0.3351(10) 0.5804(3) 0.0701(15) Uani 1 1 d . . .
H11A H 0.7261 0.1741 0.5688 0.084 Uiso 1 1 calc R . .
H11B H 0.7130 0.4284 0.5455 0.084 Uiso 1 1 calc R . .
C8 C 0.5301(2) 0.4286(11) 0.6651(5) 0.091(2) Uani 1 1 d . . .
H8 H 0.5111 0.5691 0.6828 0.109 Uiso 1 1 calc R . .
C3 C 0.6593(2) 0.5891(12) 0.7337(4) 0.0806(19) Uani 1 1 d . . .
H3 H 0.6393 0.7142 0.7589 0.097 Uiso 1 1 calc R . .
C22 C 0.8444(3) 0.5992(11) 0.8035(3) 0.0665(16) Uani 1 1 d . . .
O5 O 0.9205(3) 0.6525(9) 0.7259(2) 0.1111(17) Uani 1 1 d . . .
N5 N 0.8837(3) 0.1253(11) 0.9182(3) 0.126(3) Uani 1 1 d D . .
N4 N 0.8707(3) 0.7067(11) 0.7446(3) 0.0985(18) Uani 1 1 d . . .
C19 C 0.7981(3) 0.3991(10) 0.9272(3) 0.0617(14) Uani 1 1 d . . .
C23 C 0.8740(2) 0.4174(11) 0.8346(3) 0.0678(15) Uani 1 1 d . . .
H23 H 0.9094 0.3617 0.8159 0.081 Uiso 1 1 calc R . .
C24 C 0.8512(2) 0.3210(9) 0.8925(3) 0.0630(13) Uani 1 1 d D . .
O6 O 0.9302(3) 0.0966(13) 0.9110(6) 0.291(7) Uani 1 1 d D . .
N3 N 0.7122(2) 0.6722(12) 0.9127(3) 0.0857(16) Uani 1 1 d . . .
C21 C 0.7925(3) 0.6738(10) 0.8305(3) 0.0688(15) Uani 1 1 d . . .
H21 H 0.7721 0.7935 0.8088 0.083 Uiso 1 1 calc R . .
C20 C 0.7688(2) 0.5795(10) 0.8887(3) 0.0642(14) Uani 1 1 d . . .
O4 O 0.8401(4) 0.8427(12) 0.7130(3) 0.181(3) Uani 1 1 d . . .
C13 C 0.8922(3) 0.3648(13) 0.5985(3) 0.088(2) Uani 1 1 d . . .
H13 H 0.9298 0.3187 0.6138 0.105 Uiso 1 1 calc R . .
C10 C 0.5650(3) 0.0669(11) 0.6559(8) 0.134(5) Uani 1 1 d . . .
H10 H 0.5746 -0.0954 0.6651 0.161 Uiso 1 1 calc R . .
N1 N 0.79654(19) 0.3838(8) 0.5796(2) 0.0629(11) Uani 1 1 d . . .
C14 C 0.8402(3) 0.2608(12) 0.6129(3) 0.0853(18) Uani 1 1 d . . .
H14 H 0.8347 0.1302 0.6402 0.102 Uiso 1 1 calc R . .
C12 C 0.8221(3) 0.5560(10) 0.5473(3) 0.0650(15) Uani 1 1 d . . .
H12 H 0.8023 0.6661 0.5208 0.078 Uiso 1 1 calc R . .
N2 N 0.88018(19) 0.5492(9) 0.5578(3) 0.0708(13) Uani 1 1 d . . .
C6 C 0.5752(3) 0.189(2) 0.5949(6) 0.127(4) Uani 1 1 d . . .
H6 H 0.5944 0.1274 0.5533 0.152 Uiso 1 1 calc R . .
C7 C 0.5544(3) 0.4025(16) 0.6024(4) 0.099(2) Uani 1 1 d . . .
H7 H 0.5563 0.5230 0.5669 0.118 Uiso 1 1 calc R . .
O1 O 0.78139(18) 0.3262(6) 0.9847(2) 0.0826(12) Uani 1 1 d . . .
O3 O 0.6979(3) 0.8641(10) 0.8953(3) 0.119(2) Uani 1 1 d . . .
O2 O 0.6803(2) 0.5468(10) 0.9496(3) 0.1160(17) Uani 1 1 d . . .
C16 C 0.9376(3) 0.6326(15) 0.4506(5) 0.119(3) Uani 1 1 d . . .
H16A H 0.9010 0.6456 0.4240 0.143 Uiso 1 1 calc R . .
H16B H 0.9659 0.7430 0.4318 0.143 Uiso 1 1 calc R . .
C15 C 0.9243(3) 0.6990(14) 0.5243(5) 0.114(3) Uani 1 1 d . . .
H15A H 0.9611 0.6944 0.5507 0.137 Uiso 1 1 calc R . .
H15B H 0.9097 0.8566 0.5251 0.137 Uiso 1 1 calc R . .
C17 C 0.9618(3) 0.4008(16) 0.4408(4) 0.113(2) Uani 1 1 d . . .
H17A H 0.9357 0.2897 0.4630 0.136 Uiso 1 1 calc R . .
H17B H 1.0007 0.3912 0.4628 0.136 Uiso 1 1 calc R . .
O7 O 0.8593(3) -0.0242(12) 0.9498(4) 0.157(2) Uani 1 1 d D . .
C18 C 0.9680(4) 0.3401(19) 0.3664(4) 0.152(4) Uani 1 1 d . . .
H18A H 0.9307 0.2814 0.3495 0.228 Uiso 1 1 calc R . .
H18B H 0.9984 0.2244 0.3612 0.228 Uiso 1 1 calc R . .
H18C H 0.9790 0.4753 0.3406 0.228 Uiso 1 1 calc R . .


_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 C7 2.014(6) . ?
Fe1 C5 2.021(5) . ?
Fe1 C6 2.022(7) . ?
Fe1 C9 2.024(6) . ?
Fe1 C8 2.024(5) . ?
Fe1 C1 2.026(5) . ?
Fe1 C4 2.028(6) . ?
Fe1 C10 2.029(6) . ?
Fe1 C3 2.043(6) . ?
Fe1 C2 2.046(5) . ?
C1 C5 1.401(7) . ?
C1 C2 1.414(6) . ?
C1 C11 1.497(7) . ?
C2 C3 1.391(9) . ?
C2 H2 0.9800 . ?
C9 C8 1.384(9) . ?
C9 C10 1.405(12) . ?
C9 H9 0.9800 . ?
C5 C4 1.425(8) . ?
C5 H5 0.9800 . ?
C4 C3 1.418(8) . ?
C4 H4 0.9800 . ?
C11 N1 1.459(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C8 C7 1.339(10) . ?
C8 H8 0.9800 . ?
C3 H3 0.9800 . ?
C22 C21 1.345(8) . ?
C22 C23 1.383(8) . ?
C22 N4 1.424(8) . ?
O5 N4 1.215(7) . ?
N5 O6 1.061(8) . ?
N5 O7 1.193(8) . ?
N5 C24 1.436(8) . ?
N4 O4 1.210(7) . ?
C19 O1 1.246(6) . ?
C19 C24 1.437(8) . ?
C19 C20 1.441(8) . ?
C23 C24 1.350(8) . ?
C23 H23 0.9300 . ?
N3 O3 1.205(7) . ?
N3 O2 1.243(7) . ?
N3 C20 1.453(7) . ?
C21 C20 1.358(7) . ?
C21 H21 0.9300 . ?
C13 C14 1.340(9) . ?
C13 N2 1.354(8) . ?
C13 H13 0.9300 . ?
C10 C6 1.394(14) . ?
C10 H10 0.9800 . ?
N1 C12 1.309(7) . ?
N1 C14 1.369(7) . ?
C14 H14 0.9300 . ?
C12 N2 1.316(7) . ?
C12 H12 0.9300 . ?
N2 C15 1.465(9) . ?
C6 C7 1.328(11) . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
C16 C17 1.460(9) . ?
C16 C15 1.506(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.486(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C7 Fe1 C5 153.4(3) . . ?
C7 Fe1 C6 38.4(3) . . ?
C5 Fe1 C6 121.0(3) . . ?
C7 Fe1 C9 66.2(3) . . ?
C5 Fe1 C9 128.8(3) . . ?
C6 Fe1 C9 66.9(4) . . ?
C7 Fe1 C8 38.7(3) . . ?
C5 Fe1 C8 166.4(3) . . ?
C6 Fe1 C8 65.4(3) . . ?
C9 Fe1 C8 40.0(3) . . ?
C7 Fe1 C1 119.5(3) . . ?
C5 Fe1 C1 40.50(19) . . ?
C6 Fe1 C1 108.7(3) . . ?
C9 Fe1 C1 165.6(3) . . ?
C8 Fe1 C1 152.2(3) . . ?
C7 Fe1 C4 164.1(4) . . ?
C5 Fe1 C4 41.2(2) . . ?
C6 Fe1 C4 156.2(4) . . ?
C9 Fe1 C4 109.8(3) . . ?
C8 Fe1 C4 128.4(3) . . ?
C1 Fe1 C4 68.3(2) . . ?
C7 Fe1 C10 66.5(3) . . ?
C5 Fe1 C10 109.1(2) . . ?
C6 Fe1 C10 40.2(4) . . ?
C9 Fe1 C10 40.6(3) . . ?
C8 Fe1 C10 67.2(3) . . ?
C1 Fe1 C10 127.2(4) . . ?
C4 Fe1 C10 121.5(4) . . ?
C7 Fe1 C3 126.6(3) . . ?
C5 Fe1 C3 68.5(2) . . ?
C6 Fe1 C3 161.9(5) . . ?
C9 Fe1 C3 121.1(3) . . ?
C8 Fe1 C3 109.1(3) . . ?
C1 Fe1 C3 67.5(2) . . ?
C4 Fe1 C3 40.8(2) . . ?
C10 Fe1 C3 156.0(5) . . ?
C7 Fe1 C2 107.8(3) . . ?
C5 Fe1 C2 68.6(2) . . ?
C6 Fe1 C2 125.8(5) . . ?
C9 Fe1 C2 153.2(3) . . ?
C8 Fe1 C2 118.8(2) . . ?
C1 Fe1 C2 40.64(18) . . ?
C4 Fe1 C2 68.3(3) . . ?
C10 Fe1 C2 163.6(5) . . ?
C3 Fe1 C2 39.8(3) . . ?
C5 C1 C2 109.0(5) . . ?
C5 C1 C11 128.6(5) . . ?
C2 C1 C11 122.3(5) . . ?
C5 C1 Fe1 69.5(3) . . ?
C2 C1 Fe1 70.4(3) . . ?
C11 C1 Fe1 126.2(3) . . ?
C3 C2 C1 107.5(5) . . ?
C3 C2 Fe1 70.0(3) . . ?
C1 C2 Fe1 68.9(2) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
Fe1 C2 H2 126.3 . . ?
C8 C9 C10 107.1(7) . . ?
C8 C9 Fe1 70.0(3) . . ?
C10 C9 Fe1 69.9(4) . . ?
C8 C9 H9 126.5 . . ?
C10 C9 H9 126.5 . . ?
Fe1 C9 H9 126.5 . . ?
C1 C5 C4 107.3(5) . . ?
C1 C5 Fe1 70.0(3) . . ?
C4 C5 Fe1 69.6(3) . . ?
C1 C5 H5 126.4 . . ?
C4 C5 H5 126.4 . . ?
Fe1 C5 H5 126.4 . . ?
C3 C4 C5 107.3(5) . . ?
C3 C4 Fe1 70.2(4) . . ?
C5 C4 Fe1 69.2(3) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
Fe1 C4 H4 126.4 . . ?
N1 C11 C1 112.1(4) . . ?
N1 C11 H11A 109.2 . . ?
C1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C7 C8 C9 108.2(7) . . ?
C7 C8 Fe1 70.2(4) . . ?
C9 C8 Fe1 70.0(3) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
Fe1 C8 H8 125.9 . . ?
C2 C3 C4 108.9(5) . . ?
C2 C3 Fe1 70.2(3) . . ?
C4 C3 Fe1 69.0(3) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
Fe1 C3 H3 125.5 . . ?
C21 C22 C23 119.2(5) . . ?
C21 C22 N4 121.8(6) . . ?
C23 C22 N4 118.9(6) . . ?
O6 N5 O7 113.7(8) . . ?
O6 N5 C24 125.1(7) . . ?
O7 N5 C24 121.2(6) . . ?
O4 N4 O5 122.5(6) . . ?
O4 N4 C22 117.1(7) . . ?
O5 N4 C22 120.3(7) . . ?
O1 C19 C24 124.0(6) . . ?
O1 C19 C20 124.7(5) . . ?
C24 C19 C20 111.3(5) . . ?
C24 C23 C22 119.7(5) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 N5 115.0(5) . . ?
C23 C24 C19 124.6(5) . . ?
N5 C24 C19 120.4(5) . . ?
O3 N3 O2 123.3(6) . . ?
O3 N3 C20 118.8(6) . . ?
O2 N3 C20 117.9(6) . . ?
C22 C21 C20 122.0(5) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C20 C19 122.9(5) . . ?
C21 C20 N3 117.1(6) . . ?
C19 C20 N3 120.0(5) . . ?
C14 C13 N2 107.6(5) . . ?
C14 C13 H13 126.2 . . ?
N2 C13 H13 126.2 . . ?
C6 C10 C9 105.6(6) . . ?
C6 C10 Fe1 69.6(4) . . ?
C9 C10 Fe1 69.5(4) . . ?
C6 C10 H10 127.2 . . ?
C9 C10 H10 127.2 . . ?
Fe1 C10 H10 127.2 . . ?
C12 N1 C14 108.0(5) . . ?
C12 N1 C11 125.5(5) . . ?
C14 N1 C11 126.4(5) . . ?
C13 C14 N1 106.7(6) . . ?
C13 C14 H14 126.6 . . ?
N1 C14 H14 126.6 . . ?
N1 C12 N2 109.6(5) . . ?
N1 C12 H12 125.2 . . ?
N2 C12 H12 125.2 . . ?
C12 N2 C13 108.1(5) . . ?
C12 N2 C15 125.4(6) . . ?
C13 N2 C15 126.2(6) . . ?
C7 C6 C10 108.9(8) . . ?
C7 C6 Fe1 70.4(4) . . ?
C10 C6 Fe1 70.1(5) . . ?
C7 C6 H6 125.5 . . ?
C10 C6 H6 125.5 . . ?
Fe1 C6 H6 125.5 . . ?
C6 C7 C8 110.2(8) . . ?
C6 C7 Fe1 71.1(4) . . ?
C8 C7 Fe1 71.1(4) . . ?
C6 C7 H7 124.9 . . ?
C8 C7 H7 124.9 . . ?
Fe1 C7 H7 124.9 . . ?
C17 C16 C15 115.6(7) . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
N2 C15 C16 113.6(6) . . ?
N2 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
N2 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C17 C18 112.2(8) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 992136'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Fe N6 O7'
_chemical_formula_weight         510.25

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.4026(4)
_cell_length_b                   10.9599(4)
_cell_length_c                   12.3548(5)
_cell_angle_alpha                107.976(4)
_cell_angle_beta                 102.058(4)
_cell_angle_gamma                92.430(4)
_cell_volume                     1051.35(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8795
_exptl_absorpt_correction_T_max  0.9335
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            21217
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4136
_reflns_number_gt                3472
_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)+(0.0346P)²+0.6591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4136
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.12863(4) 0.76716(3) 0.52437(3) 0.04244(12) Uani 1 1 d . . .
N1 N 0.2449(2) 0.96994(15) 0.90478(14) 0.0312(4) Uani 1 1 d . . .
N2 N 0.1545(2) 1.07224(16) 0.91847(15) 0.0359(4) Uani 1 1 d . . .
N3 N 0.2362(2) 1.03198(15) 1.08395(14) 0.0305(4) Uani 1 1 d . . .
N4 N 0.4459(3) 0.4366(2) 0.25079(17) 0.0489(5) Uani 1 1 d . . .
N5 N 0.3713(2) 0.25060(17) -0.17644(16) 0.0402(4) Uani 1 1 d . . .
N6 N 0.1343(2) 0.64004(17) -0.01185(17) 0.0395(4) Uani 1 1 d . . .
O1 O 0.0792(2) 0.64004(18) -0.11174(16) 0.0620(5) Uani 1 1 d . . .
O7 O 0.4970(2) 0.25124(14) 0.06186(14) 0.0452(4) Uani 1 1 d . . .
O8 O 0.5618(3) 0.5137(3) 0.31047(19) 0.0957(8) Uani 1 1 d . . .
O9 O 0.3822(3) 0.3572(2) 0.28191(18) 0.0868(7) Uani 1 1 d . . .
O10 O 0.4903(2) 0.19058(16) -0.16829(15) 0.0545(5) Uani 1 1 d . . .
O11 O 0.2718(3) 0.23200(19) -0.26847(15) 0.0683(6) Uani 1 1 d . . .
O12 O 0.1147(2) 0.72476(16) 0.07376(16) 0.0578(5) Uani 1 1 d . . .
C1 C 0.1316(3) 0.8518(2) 0.69567(18) 0.0386(5) Uani 1 1 d . . .
C2 C 0.0537(4) 0.7233(3) 0.6556(2) 0.0624(8) Uani 1 1 d . . .
H2 H 0.0874 0.6537 0.6865 0.075 Uiso 1 1 calc R . .
C3 C -0.0828(4) 0.7146(4) 0.5624(2) 0.0793(11) Uani 1 1 d . . .
H3 H -0.1588 0.6368 0.5168 0.095 Uiso 1 1 calc R . .
C4 C -0.0890(3) 0.8346(4) 0.5451(2) 0.0663(9) Uani 1 1 d . . .
H4 H -0.1701 0.8552 0.4857 0.080 Uiso 1 1 calc R . .
C5 C 0.0422(3) 0.9203(3) 0.62683(19) 0.0463(6) Uani 1 1 d . . .
H5 H 0.0680 1.0111 0.6347 0.056 Uiso 1 1 calc R . .
C6 C 0.3631(4) 0.7636(4) 0.5042(3) 0.0748(9) Uani 1 1 d . . .
H6 H 0.4628 0.7974 0.5666 0.090 Uiso 1 1 calc R . .
C7 C 0.2852(5) 0.6393(3) 0.4650(3) 0.0753(9) Uani 1 1 d . . .
H7 H 0.3196 0.5691 0.4949 0.090 Uiso 1 1 calc R . .
C8 C 0.1481(4) 0.6309(3) 0.3746(2) 0.0707(9) Uani 1 1 d . . .
H8 H 0.0704 0.5537 0.3304 0.085 Uiso 1 1 calc R . .
C9 C 0.1417(4) 0.7505(3) 0.3582(2) 0.0619(8) Uani 1 1 d . . .
H9 H 0.0593 0.7723 0.3004 0.074 Uiso 1 1 calc R . .
C10 C 0.2740(4) 0.8330(3) 0.4371(3) 0.0704(9) Uani 1 1 d . . .
H10A H 0.3012 0.9237 0.4450 0.084 Uiso 1 1 calc R . .
C11 C 0.2824(3) 0.9047(2) 0.79014(18) 0.0385(5) Uani 1 1 d . . .
H11A H 0.3472 0.8350 0.7965 0.046 Uiso 1 1 calc R . .
H11B H 0.3472 0.9659 0.7697 0.046 Uiso 1 1 calc R . .
C12 C 0.2932(2) 0.94632(19) 1.00336(17) 0.0308(4) Uani 1 1 d . . .
H12A H 0.3558 0.8815 1.0148 0.037 Uiso 1 1 calc R . .
C13 C 0.1520(2) 1.10724(19) 1.02816(18) 0.0342(5) Uani 1 1 d . . .
H13 H 0.0991 1.1756 1.0645 0.041 Uiso 1 1 calc R . .
C14 C 0.2544(3) 1.0402(2) 1.20654(19) 0.0442(5) Uani 1 1 d . . .
H14A H 0.1543 1.0043 1.2164 0.066 Uiso 1 1 calc R . .
H14B H 0.2789 1.1290 1.2553 0.066 Uiso 1 1 calc R . .
H14C H 0.3420 0.9927 1.2283 0.066 Uiso 1 1 calc R . .
C15 C 0.3779(3) 0.4404(2) 0.13278(18) 0.0340(5) Uani 1 1 d . . .
C16 C 0.4160(2) 0.33701(18) 0.04026(18) 0.0314(4) Uani 1 1 d . . .
C17 C 0.3463(2) 0.34674(18) -0.07276(18) 0.0310(4) Uani 1 1 d . . .
C18 C 0.2532(2) 0.44207(19) -0.08973(18) 0.0332(4) Uani 1 1 d . . .
H18 H 0.2083 0.4424 -0.1651 0.040 Uiso 1 1 calc R . .
C19 C 0.2267(2) 0.53701(19) 0.00531(19) 0.0326(4) Uani 1 1 d . . .
C20 C 0.2908(3) 0.5377(2) 0.11912(19) 0.0350(5) Uani 1 1 d . . .
H20 H 0.2743 0.6029 0.1834 0.042 Uiso 1 1 calc R . .


_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 C1 2.026(2) . ?
Fe1 C5 2.030(2) . ?
Fe1 C9 2.031(2) . ?
Fe1 C8 2.031(3) . ?
Fe1 C10 2.032(3) . ?
Fe1 C3 2.034(3) . ?
Fe1 C2 2.034(2) . ?
Fe1 C4 2.037(3) . ?
Fe1 C6 2.037(3) . ?
Fe1 C7 2.040(3) . ?
N1 C12 1.308(3) . ?
N1 N2 1.368(2) . ?
N1 C11 1.482(3) . ?
N2 C13 1.295(3) . ?
N3 C12 1.328(2) . ?
N3 C13 1.361(3) . ?
N3 C14 1.464(3) . ?
N4 O9 1.202(3) . ?
N4 O8 1.205(3) . ?
N4 C15 1.465(3) . ?
N5 O11 1.216(2) . ?
N5 O10 1.224(2) . ?
N5 C17 1.447(3) . ?
N6 O12 1.220(2) . ?
N6 O1 1.224(2) . ?
N6 C19 1.441(2) . ?
O7 C16 1.246(2) . ?
C1 C2 1.418(3) . ?
C1 C5 1.423(3) . ?
C1 C11 1.486(3) . ?
C2 C3 1.422(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.397(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.407(4) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C7 1.380(5) . ?
C6 C10 1.416(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.405(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.351(3) . ?
C15 C16 1.441(3) . ?
C16 C17 1.435(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(3) . ?
C20 H20 0.9300 . ?

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
C1 Fe1 C5 41.08(9) . . ?
C1 Fe1 C9 159.22(11) . . ?
C5 Fe1 C9 122.33(11) . . ?
C1 Fe1 C8 159.77(11) . . ?
C5 Fe1 C8 157.45(12) . . ?
C9 Fe1 C8 39.97(12) . . ?
C1 Fe1 C10 124.42(12) . . ?
C5 Fe1 C10 108.58(12) . . ?
C9 Fe1 C10 39.90(13) . . ?
C8 Fe1 C10 66.98(14) . . ?
C1 Fe1 C3 68.49(10) . . ?
C5 Fe1 C3 67.96(13) . . ?
C9 Fe1 C3 121.79(13) . . ?
C8 Fe1 C3 107.24(14) . . ?
C10 Fe1 C3 157.67(15) . . ?
C1 Fe1 C2 40.89(10) . . ?
C5 Fe1 C2 68.79(11) . . ?
C9 Fe1 C2 158.09(12) . . ?
C8 Fe1 C2 122.98(13) . . ?
C10 Fe1 C2 160.45(14) . . ?
C3 Fe1 C2 40.92(12) . . ?
C1 Fe1 C4 68.63(10) . . ?
C5 Fe1 C4 40.47(11) . . ?
C9 Fe1 C4 106.66(11) . . ?
C8 Fe1 C4 121.70(13) . . ?
C10 Fe1 C4 122.86(14) . . ?
C3 Fe1 C4 40.15(14) . . ?
C2 Fe1 C4 68.56(13) . . ?
C1 Fe1 C6 109.31(11) . . ?
C5 Fe1 C6 124.92(13) . . ?
C9 Fe1 C6 67.82(12) . . ?
C8 Fe1 C6 67.25(14) . . ?
C10 Fe1 C6 40.72(13) . . ?
C3 Fe1 C6 159.20(17) . . ?
C2 Fe1 C6 123.77(14) . . ?
C4 Fe1 C6 160.04(16) . . ?
C1 Fe1 C7 124.20(11) . . ?
C5 Fe1 C7 160.57(13) . . ?
C9 Fe1 C7 67.65(12) . . ?
C8 Fe1 C7 40.38(13) . . ?
C10 Fe1 C7 67.31(14) . . ?
C3 Fe1 C7 123.29(16) . . ?
C2 Fe1 C7 108.33(13) . . ?
C4 Fe1 C7 158.02(15) . . ?
C6 Fe1 C7 39.57(14) . . ?
C12 N1 N2 111.25(16) . . ?
C12 N1 C11 128.28(17) . . ?
N2 N1 C11 120.41(16) . . ?
C13 N2 N1 103.57(16) . . ?
C12 N3 C13 105.93(17) . . ?
C12 N3 C14 126.96(17) . . ?
C13 N3 C14 127.06(17) . . ?
O9 N4 O8 124.3(2) . . ?
O9 N4 C15 117.9(2) . . ?
O8 N4 C15 117.8(2) . . ?
O11 N5 O10 122.56(19) . . ?
O11 N5 C17 118.34(18) . . ?
O10 N5 C17 119.10(18) . . ?
O12 N6 O1 122.29(18) . . ?
O12 N6 C19 118.81(18) . . ?
O1 N6 C19 118.90(19) . . ?
C2 C1 C5 107.8(2) . . ?
C2 C1 C11 126.3(2) . . ?
C5 C1 C11 125.9(2) . . ?
C2 C1 Fe1 69.85(13) . . ?
C5 C1 Fe1 69.62(12) . . ?
C11 C1 Fe1 124.62(15) . . ?
C1 C2 C3 107.1(3) . . ?
C1 C2 Fe1 69.25(13) . . ?
C3 C2 Fe1 69.53(15) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
Fe1 C2 H2 126.5 . . ?
C4 C3 C2 108.9(3) . . ?
C4 C3 Fe1 70.05(17) . . ?
C2 C3 Fe1 69.55(16) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 125.6 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 Fe1 69.81(19) . . ?
C5 C4 Fe1 69.52(14) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C4 C5 C1 108.1(2) . . ?
C4 C5 Fe1 70.01(16) . . ?
C1 C5 Fe1 69.30(13) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 107.6(3) . . ?
C7 C6 Fe1 70.31(19) . . ?
C10 C6 Fe1 69.46(17) . . ?
C7 C6 H6 126.2 . . ?
C10 C6 H6 126.2 . . ?
Fe1 C6 H6 126.2 . . ?
C6 C7 C8 108.0(3) . . ?
C6 C7 Fe1 70.12(17) . . ?
C8 C7 Fe1 69.47(17) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
Fe1 C7 H7 126.0 . . ?
C9 C8 C7 108.4(3) . . ?
C9 C8 Fe1 70.01(15) . . ?
C7 C8 Fe1 70.15(16) . . ?
C9 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
Fe1 C8 H8 125.8 . . ?
C10 C9 C8 107.8(3) . . ?
C10 C9 Fe1 70.12(16) . . ?
C8 C9 Fe1 70.02(15) . . ?
C10 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
Fe1 C9 H9 126.1 . . ?
C9 C10 C6 108.1(3) . . ?
C9 C10 Fe1 69.98(17) . . ?
C6 C10 Fe1 69.82(17) . . ?
C9 C10 H10A 125.9 . . ?
C6 C10 H10A 125.9 . . ?
Fe1 C10 H10A 125.9 . . ?
N1 C11 C1 112.11(17) . . ?
N1 C11 H11A 109.2 . . ?
C1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 N3 107.36(17) . . ?
N1 C12 H12A 126.3 . . ?
N3 C12 H12A 126.3 . . ?
N2 C13 N3 111.88(17) . . ?
N2 C13 H13 124.1 . . ?
N3 C13 H13 124.1 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 126.03(19) . . ?
C20 C15 N4 119.51(19) . . ?
C16 C15 N4 114.44(17) . . ?
O7 C16 C17 127.18(19) . . ?
O7 C16 C15 121.21(19) . . ?
C17 C16 C15 111.59(17) . . ?
C18 C17 C16 123.78(18) . . ?
C18 C17 N5 116.83(18) . . ?
C16 C17 N5 119.38(17) . . ?
C17 C18 C19 119.58(19) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 121.29(18) . . ?
C18 C19 N6 119.80(19) . . ?
C20 C19 N6 118.90(18) . . ?
C15 C20 C19 117.69(19) . . ?
C15 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 997738'
