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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_1
#TrackingRef '17282_web_deposit_cif_file_0_HaiyingZhao_1359425289.guole3h.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Fe N3 O2'
_chemical_formula_weight         347.15

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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.961(2)
_cell_length_b                   12.6449(16)
_cell_length_c                   7.1365(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.320(2)
_cell_angle_gamma                90.00
_cell_volume                     1436.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5300
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.32

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10344
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.40
_reflns_number_total             3608
_reflns_number_gt                3051
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     mixed
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 0.641117(13) 0.006123(16) 0.77610(3) 0.02852(11) Uani 1 1 d . . .
O1 O 0.85650(8) 0.10630(13) 0.67052(16) 0.0496(4) Uani 1 1 d . . .
O2 O 1.01679(8) 0.11694(11) 0.61410(16) 0.0435(3) Uani 1 1 d . . .
N1 N 0.78775(9) 0.11536(11) 1.23481(17) 0.0337(3) Uani 1 1 d . . .
N2 N 0.86923(9) 0.12003(12) 1.28923(19) 0.0350(3) Uani 1 1 d . . .
H21 H 0.8868 0.1205 1.4062 0.042 Uiso 1 1 d R . .
N3 N 0.92154(9) 0.12407(11) 1.15651(17) 0.0326(3) Uani 1 1 d . . .
C1 C 0.65300(15) -0.15314(16) 0.8238(3) 0.0524(5) Uani 1 1 d . . .
H1 H 0.6545 -0.1881 0.9466 0.063 Uiso 1 1 d R . .
C2 C 0.69424(11) -0.06824(15) 0.5611(2) 0.0425(4) Uani 1 1 d . . .
H2 H 0.7290 -0.0351 0.4700 0.051 Uiso 1 1 d R . .
C3 C 0.72391(13) -0.11337(15) 0.7370(3) 0.0474(4) Uani 1 1 d . . .
H3 H 0.7826 -0.1164 0.7883 0.057 Uiso 1 1 d R . .
C4 C 0.60559(11) -0.08030(15) 0.5416(3) 0.0439(4) Uani 1 1 d . . .
H4 H 0.5683 -0.0563 0.4347 0.053 Uiso 1 1 d R . .
C5 C 0.58003(14) -0.13287(16) 0.7031(3) 0.0484(5) Uani 1 1 d . . .
H5 H 0.5222 -0.1511 0.7281 0.058 Uiso 1 1 d R . .
C6 C 0.70291(10) 0.11808(12) 0.9422(2) 0.0300(3) Uani 1 1 d . . .
C7 C 0.67990(11) 0.15962(13) 0.7593(2) 0.0356(4) Uani 1 1 d . . .
H7 H 0.7185 0.1876 0.6710 0.043 Uiso 1 1 d R . .
C8 C 0.62715(11) 0.08621(15) 1.0219(2) 0.0383(4) Uani 1 1 d . . .
H8 H 0.6234 0.0542 1.1460 0.046 Uiso 1 1 d R . .
C9 C 0.59067(12) 0.15410(14) 0.7289(3) 0.0412(4) Uani 1 1 d . . .
H9 H 0.5573 0.1768 0.6152 0.049 Uiso 1 1 d R . .
C10 C 0.55881(11) 0.10820(14) 0.8901(3) 0.0424(4) Uani 1 1 d . . .
H10 H 0.4995 0.0940 0.9069 0.051 Uiso 1 1 d R . .
C11 C 0.78568(10) 0.11651(11) 1.0469(2) 0.0283(3) Uani 1 1 d . . .
C12 C 0.87003(9) 0.12176(12) 0.99771(19) 0.0285(3) Uani 1 1 d . . .
C13 C 0.90410(10) 0.11807(13) 0.8125(2) 0.0311(3) Uani 1 1 d . . .
C14 C 0.99425(10) 0.12636(12) 0.7955(2) 0.0317(3) Uani 1 1 d . . .
C15 C 1.06416(11) 0.14178(15) 0.9121(3) 0.0406(4) Uani 1 1 d . . .
H15 H 1.0664 0.1503 1.0418 0.049 Uiso 1 1 calc R . .
C16 C 1.13329(12) 0.14243(18) 0.7983(3) 0.0507(5) Uani 1 1 d . . .
H16 H 1.1896 0.1515 0.8388 0.061 Uiso 1 1 calc R . .
C17 C 1.10174(12) 0.12758(17) 0.6224(3) 0.0508(5) Uani 1 1 d . . .
H17 H 1.1336 0.1248 0.5187 0.061 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.02687(17) 0.03076(17) 0.02805(16) -0.00045(7) 0.00282(10) -0.00306(7)
O1 0.0353(6) 0.0936(11) 0.0195(5) -0.0036(6) -0.0004(4) -0.0087(6)
O2 0.0375(6) 0.0626(8) 0.0316(6) 0.0018(5) 0.0103(5) 0.0040(6)
N1 0.0365(7) 0.0418(7) 0.0232(6) -0.0013(5) 0.0039(5) 0.0005(6)
N2 0.0415(8) 0.0447(8) 0.0183(6) -0.0011(5) -0.0002(5) -0.0008(6)
N3 0.0364(7) 0.0410(7) 0.0201(6) -0.0017(5) -0.0016(5) -0.0023(6)
C1 0.0741(14) 0.0325(9) 0.0509(11) 0.0042(8) 0.0069(10) -0.0021(9)
C2 0.0392(9) 0.0504(10) 0.0388(9) -0.0074(8) 0.0095(7) -0.0005(8)
C3 0.0418(10) 0.0471(11) 0.0530(11) -0.0077(8) 0.0013(8) 0.0110(8)
C4 0.0412(9) 0.0502(10) 0.0399(9) -0.0133(8) -0.0003(7) -0.0057(8)
C5 0.0485(11) 0.0409(10) 0.0568(12) -0.0117(8) 0.0104(9) -0.0154(8)
C6 0.0303(7) 0.0315(8) 0.0281(7) -0.0023(6) 0.0011(6) -0.0008(6)
C7 0.0365(9) 0.0331(8) 0.0362(8) 0.0057(6) -0.0047(6) -0.0046(7)
C8 0.0354(8) 0.0464(9) 0.0340(8) -0.0070(7) 0.0084(6) -0.0018(7)
C9 0.0371(9) 0.0351(9) 0.0496(10) 0.0016(7) -0.0087(8) 0.0028(7)
C10 0.0272(8) 0.0469(10) 0.0532(10) -0.0115(8) 0.0045(7) 0.0014(7)
C11 0.0340(8) 0.0286(7) 0.0223(7) -0.0006(5) 0.0017(5) -0.0013(6)
C12 0.0313(7) 0.0341(8) 0.0196(6) -0.0015(5) -0.0014(5) -0.0014(6)
C13 0.0330(8) 0.0383(8) 0.0218(7) -0.0007(6) 0.0000(6) -0.0025(6)
C14 0.0343(8) 0.0349(8) 0.0262(7) 0.0010(6) 0.0046(6) 0.0011(6)
C15 0.0339(9) 0.0472(10) 0.0400(9) -0.0004(7) -0.0010(7) -0.0008(7)
C16 0.0314(9) 0.0559(12) 0.0650(13) 0.0072(10) 0.0052(9) -0.0020(8)
C17 0.0380(10) 0.0592(12) 0.0576(12) 0.0088(9) 0.0202(9) 0.0060(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C2 2.0380(17) . ?
Fe1 C3 2.0403(18) . ?
Fe1 C4 2.0431(17) . ?
Fe1 C7 2.0435(17) . ?
Fe1 C6 2.0508(15) . ?
Fe1 C1 2.049(2) . ?
Fe1 C9 2.0548(18) . ?
Fe1 C10 2.0530(17) . ?
Fe1 C8 2.0519(16) . ?
Fe1 C5 2.0578(19) . ?
O1 C13 1.2292(18) . ?
O2 C17 1.359(2) . ?
O2 C14 1.3745(18) . ?
N1 N2 1.330(2) . ?
N1 C11 1.3394(19) . ?
N2 N3 1.310(2) . ?
N2 H21 0.8600 . ?
N3 C12 1.3493(18) . ?
C1 C5 1.419(3) . ?
C1 C3 1.423(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.427(3) . ?
C2 C4 1.419(2) . ?
C2 H2 0.9799 . ?
C3 H3 0.9801 . ?
C4 C5 1.417(3) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C7 1.429(2) . ?
C6 C8 1.432(2) . ?
C6 C11 1.468(2) . ?
C7 C9 1.426(3) . ?
C7 H7 0.9800 . ?
C8 C10 1.413(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.417(3) . ?
C9 H9 0.9800 . ?
C10 H10 0.9801 . ?
C11 C12 1.418(2) . ?
C12 C13 1.467(2) . ?
C13 C14 1.457(2) . ?
C14 C15 1.355(2) . ?
C15 C16 1.418(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.330(3) . ?
C16 H16 0.9300 . ?
C17 H17 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
C2 Fe1 C3 40.96(8) . . ?
C2 Fe1 C4 40.71(7) . . ?
C3 Fe1 C4 68.56(8) . . ?
C2 Fe1 C7 104.42(8) . . ?
C3 Fe1 C7 119.55(7) . . ?
C4 Fe1 C7 121.77(7) . . ?
C2 Fe1 C6 122.99(7) . . ?
C3 Fe1 C6 107.58(7) . . ?
C4 Fe1 C6 159.14(7) . . ?
C7 Fe1 C6 40.86(6) . . ?
C2 Fe1 C1 68.48(8) . . ?
C3 Fe1 C1 40.72(9) . . ?
C4 Fe1 C1 68.10(9) . . ?
C7 Fe1 C1 156.73(9) . . ?
C6 Fe1 C1 123.22(8) . . ?
C2 Fe1 C9 118.48(8) . . ?
C3 Fe1 C9 154.39(9) . . ?
C4 Fe1 C9 105.76(8) . . ?
C7 Fe1 C9 40.73(7) . . ?
C6 Fe1 C9 68.39(7) . . ?
C1 Fe1 C9 162.28(9) . . ?
C2 Fe1 C10 154.60(8) . . ?
C3 Fe1 C10 163.79(9) . . ?
C4 Fe1 C10 120.96(8) . . ?
C7 Fe1 C10 68.40(7) . . ?
C6 Fe1 C10 68.36(7) . . ?
C1 Fe1 C10 127.31(8) . . ?
C9 Fe1 C10 40.35(8) . . ?
C2 Fe1 C8 161.70(7) . . ?
C3 Fe1 C8 126.56(8) . . ?
C4 Fe1 C8 157.36(7) . . ?
C7 Fe1 C8 68.55(7) . . ?
C6 Fe1 C8 40.86(7) . . ?
C1 Fe1 C8 110.95(8) . . ?
C9 Fe1 C8 67.94(8) . . ?
C10 Fe1 C8 40.28(7) . . ?
C2 Fe1 C5 68.36(8) . . ?
C3 Fe1 C5 68.42(9) . . ?
C4 Fe1 C5 40.42(8) . . ?
C7 Fe1 C5 159.42(9) . . ?
C6 Fe1 C5 159.07(8) . . ?
C1 Fe1 C5 40.43(9) . . ?
C9 Fe1 C5 124.33(9) . . ?
C10 Fe1 C5 109.40(8) . . ?
C8 Fe1 C5 123.93(8) . . ?
C17 O2 C14 106.33(15) . . ?
N2 N1 C11 103.99(12) . . ?
N3 N2 N1 116.94(13) . . ?
N3 N2 H21 121.5 . . ?
N1 N2 H21 121.5 . . ?
N2 N3 C12 103.01(13) . . ?
C5 C1 C3 108.36(19) . . ?
C5 C1 Fe1 70.13(11) . . ?
C3 C1 Fe1 69.32(11) . . ?
C5 C1 H1 126.0 . . ?
C3 C1 H1 125.6 . . ?
Fe1 C1 H1 126.0 . . ?
C3 C2 C4 107.81(17) . . ?
C3 C2 Fe1 69.61(10) . . ?
C4 C2 Fe1 69.84(10) . . ?
C3 C2 H2 126.0 . . ?
C4 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C1 C3 C2 107.60(18) . . ?
C1 C3 Fe1 69.97(11) . . ?
C2 C3 Fe1 69.43(10) . . ?
C1 C3 H3 126.3 . . ?
C2 C3 H3 126.1 . . ?
Fe1 C3 H3 126.1 . . ?
C5 C4 C2 108.44(18) . . ?
C5 C4 Fe1 70.35(11) . . ?
C2 C4 Fe1 69.45(10) . . ?
C5 C4 H4 125.7 . . ?
C2 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C4 C5 C1 107.78(18) . . ?
C4 C5 Fe1 69.23(10) . . ?
C1 C5 Fe1 69.45(11) . . ?
C4 C5 H5 126.2 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.1 . . ?
C7 C6 C8 107.43(15) . . ?
C7 C6 C11 128.99(15) . . ?
C8 C6 C11 123.27(14) . . ?
C7 C6 Fe1 69.30(9) . . ?
C8 C6 Fe1 69.61(9) . . ?
C11 C6 Fe1 131.30(11) . . ?
C9 C7 C6 107.82(16) . . ?
C9 C7 Fe1 70.06(9) . . ?
C6 C7 Fe1 69.85(9) . . ?
C9 C7 H7 126.0 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 126.1 . . ?
C10 C8 C6 108.23(15) . . ?
C10 C8 Fe1 69.90(10) . . ?
C6 C8 Fe1 69.53(9) . . ?
C10 C8 H8 125.9 . . ?
C6 C8 H8 125.9 . . ?
Fe1 C8 H8 125.9 . . ?
C10 C9 C7 108.17(15) . . ?
C10 C9 Fe1 69.75(10) . . ?
C7 C9 Fe1 69.21(9) . . ?
C10 C9 H9 125.9 . . ?
C7 C9 H9 125.9 . . ?
Fe1 C9 H9 125.8 . . ?
C9 C10 C8 108.34(15) . . ?
C9 C10 Fe1 69.89(10) . . ?
C8 C10 Fe1 69.82(10) . . ?
C9 C10 H10 125.7 . . ?
C8 C10 H10 125.9 . . ?
Fe1 C10 H10 125.9 . . ?
N1 C11 C12 107.21(13) . . ?
N1 C11 C6 117.59(14) . . ?
C12 C11 C6 135.10(14) . . ?
N3 C12 C11 108.85(13) . . ?
N3 C12 C13 120.89(14) . . ?
C11 C12 C13 130.13(13) . . ?
O1 C13 C14 119.53(14) . . ?
O1 C13 C12 119.90(14) . . ?
C14 C13 C12 120.56(13) . . ?
C15 C14 O2 109.21(15) . . ?
C15 C14 C13 137.04(15) . . ?
O2 C14 C13 113.75(14) . . ?
C14 C15 C16 106.83(17) . . ?
C14 C15 H15 126.6 . . ?
C16 C15 H15 126.6 . . ?
C17 C16 C15 106.49(17) . . ?
C17 C16 H16 126.8 . . ?
C15 C16 H16 126.8 . . ?
C16 C17 O2 111.14(17) . . ?
C16 C17 H17 124.4 . . ?
O2 C17 H17 124.4 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.052


_database_code_depnum_ccdc_archive 'CCDC 922174'