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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  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_sample1

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H14 Fe I N O4'
_chemical_formula_moiety         'C14 H14 Fe I N O4'
_chemical_formula_weight         443.02
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.997(3)
_cell_length_b                   7.231(3)
_cell_length_c                   15.311(6)
_cell_angle_alpha                93.523(5)
_cell_angle_beta                 97.073(4)
_cell_angle_gamma                101.321(6)
_cell_volume                     750.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2853
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      30.64
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432.00
_exptl_absorpt_coefficient_mu    3.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.912

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            9145
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3556
_reflns_number_gt                3058
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0484
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         3556
_refine_ls_number_parameters     246
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0233P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.570
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Fe Fe 0.3463 0.8444
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
I1 I -0.05850(2) 0.649281(19) 0.093939(9) 0.02313(6) Uani 1.0 2 d . . .
Fe1 Fe 0.27509(4) 1.08602(4) 0.198580(18) 0.01263(7) Uani 1.0 2 d . . .
O1 O 0.4376(3) 0.7219(3) 0.53038(10) 0.0183(4) Uani 1.0 2 d . . .
O4 O 0.3926(3) 0.5409(2) 0.40248(9) 0.0188(4) Uani 1.0 2 d . . .
O5 O -0.2370(3) 0.8538(3) 0.38672(13) 0.0369(5) Uani 1.0 2 d . . .
O6 O -0.1032(3) 0.7152(3) 0.49140(11) 0.0341(5) Uani 1.0 2 d . . .
N1 N -0.1384(3) 0.7415(3) 0.41352(12) 0.0193(4) Uani 1.0 2 d . . .
C1 C 0.0150(3) 0.9005(3) 0.17628(13) 0.0130(4) Uani 1.0 2 d . . .
C2 C 0.0906(3) 0.9192(3) 0.26869(12) 0.0109(4) Uani 1.0 2 d . . .
C3 C 0.1093(3) 1.1140(3) 0.29843(14) 0.0138(4) Uani 1.0 2 d . . .
C4 C 0.0481(3) 1.2114(3) 0.22582(14) 0.0174(5) Uani 1.0 2 d . . .
C5 C -0.0121(3) 1.0806(3) 0.14987(14) 0.0153(5) Uani 1.0 2 d . . .
C6 C 0.4557(4) 1.0049(5) 0.11495(17) 0.0330(7) Uani 1.0 2 d . . .
C7 C 0.5319(4) 0.9888(4) 0.20270(16) 0.0278(6) Uani 1.0 2 d . . .
C8 C 0.5666(4) 1.1679(4) 0.24946(17) 0.0288(6) Uani 1.0 2 d . . .
C9 C 0.5115(4) 1.2972(4) 0.1902(2) 0.0354(7) Uani 1.0 2 d . . .
C10 C 0.4433(4) 1.1951(5) 0.10655(18) 0.0380(8) Uani 1.0 2 d . . .
C11 C 0.1367(3) 0.7625(3) 0.32300(13) 0.0107(4) Uani 1.0 2 d . . .
C12 C 0.2888(3) 0.8373(3) 0.40404(13) 0.0119(4) Uani 1.0 2 d . . .
C13 C 0.3762(3) 0.6847(3) 0.44531(13) 0.0128(4) Uani 1.0 2 d . . .
C14 C -0.0493(4) 0.6353(3) 0.34774(14) 0.0153(5) Uani 1.0 2 d . . .
H1 H 0.160(3) 1.166(3) 0.3548(15) 0.012(6) Uiso 1.0 2 d . . .
H2 H 0.049(4) 1.343(4) 0.2276(16) 0.024(7) Uiso 1.0 2 d . . .
H3 H -0.062(3) 1.108(3) 0.0920(15) 0.014(6) Uiso 1.0 2 d . . .
H4 H 0.184(3) 0.680(3) 0.2854(14) 0.009(6) Uiso 1.0 2 d . . .
H5 H 0.395(3) 0.918(3) 0.3850(14) 0.009(6) Uiso 1.0 2 d . . .
H6 H 0.235(3) 0.901(3) 0.4462(14) 0.008(5) Uiso 1.0 2 d . . .
H7 H -0.019(4) 0.527(4) 0.3771(15) 0.021(7) Uiso 1.0 2 d . . .
H8 H -0.145(4) 0.590(4) 0.2966(16) 0.019(6) Uiso 1.0 2 d . . .
H9 H 0.422(5) 0.905(5) 0.070(2) 0.057(10) Uiso 1.0 2 d . . .
H10 H 0.559(4) 0.871(4) 0.2267(18) 0.037(8) Uiso 1.0 2 d . . .
H11 H 0.614(4) 1.202(4) 0.313(2) 0.045(8) Uiso 1.0 2 d . . .
H12 H 0.512(4) 1.415(4) 0.2044(18) 0.032(8) Uiso 1.0 2 d . . .
H13 H 0.400(4) 1.242(4) 0.0626(19) 0.033(8) Uiso 1.0 2 d . . .
H14 H 0.487(5) 0.641(5) 0.549(2) 0.047(10) Uiso 1.0 2 d . . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
I1 C1 2.085(2) yes . .
Fe1 C1 2.0149(19) yes . .
Fe1 C2 2.040(2) yes . .
Fe1 C3 2.053(3) yes . .
Fe1 C4 2.049(3) yes . .
Fe1 C5 2.047(3) yes . .
Fe1 C6 2.044(3) yes . .
Fe1 C7 2.049(3) yes . .
Fe1 C8 2.048(3) yes . .
Fe1 C9 2.041(3) yes . .
Fe1 C10 2.043(3) yes . .
O1 C13 1.314(3) yes . .
O4 C13 1.228(3) yes . .
O5 N1 1.223(3) yes . .
O6 N1 1.222(3) yes . .
N1 C14 1.496(3) yes . .
C1 C2 1.437(3) yes . .
C1 C5 1.428(3) yes . .
C2 C3 1.429(3) yes . .
C2 C11 1.508(3) yes . .
C3 C4 1.419(4) yes . .
C4 C5 1.419(3) yes . .
C6 C7 1.404(4) yes . .
C6 C10 1.408(5) yes . .
C7 C8 1.403(4) yes . .
C8 C9 1.416(5) yes . .
C9 C10 1.418(4) yes . .
C11 C12 1.527(3) yes . .
C11 C14 1.542(3) yes . .
C12 C13 1.498(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 Fe1 C2 41.50(8) yes . . .
C1 Fe1 C3 68.61(8) yes . . .
C1 Fe1 C4 68.45(9) yes . . .
C1 Fe1 C5 41.14(9) yes . . .
C1 Fe1 C6 108.45(10) yes . . .
C1 Fe1 C7 119.70(10) yes . . .
C1 Fe1 C8 153.27(10) yes . . .
C1 Fe1 C9 164.88(11) yes . . .
C1 Fe1 C10 127.27(10) yes . . .
C2 Fe1 C3 40.88(8) yes . . .
C2 Fe1 C4 68.92(9) yes . . .
C2 Fe1 C5 69.72(9) yes . . .
C2 Fe1 C6 128.10(11) yes . . .
C2 Fe1 C7 108.57(10) yes . . .
C2 Fe1 C8 118.65(10) yes . . .
C2 Fe1 C9 152.20(10) yes . . .
C2 Fe1 C10 165.79(10) yes . . .
C3 Fe1 C4 40.47(9) yes . . .
C3 Fe1 C5 68.54(9) yes . . .
C3 Fe1 C6 166.22(11) yes . . .
C3 Fe1 C7 128.60(10) yes . . .
C3 Fe1 C8 108.57(10) yes . . .
C3 Fe1 C9 118.42(11) yes . . .
C3 Fe1 C10 152.11(12) yes . . .
C4 Fe1 C5 40.52(9) yes . . .
C4 Fe1 C6 152.32(11) yes . . .
C4 Fe1 C7 165.64(9) yes . . .
C4 Fe1 C8 127.70(10) yes . . .
C4 Fe1 C9 107.46(11) yes . . .
C4 Fe1 C10 118.27(12) yes . . .
C5 Fe1 C6 118.76(10) yes . . .
C5 Fe1 C7 153.19(9) yes . . .
C5 Fe1 C8 164.67(10) yes . . .
C5 Fe1 C9 126.44(11) yes . . .
C5 Fe1 C10 107.13(10) yes . . .
C6 Fe1 C7 40.11(11) yes . . .
C6 Fe1 C8 67.60(11) yes . . .
C6 Fe1 C9 67.97(12) yes . . .
C6 Fe1 C10 40.30(14) yes . . .
C7 Fe1 C8 40.04(11) yes . . .
C7 Fe1 C9 67.76(12) yes . . .
C7 Fe1 C10 67.62(12) yes . . .
C8 Fe1 C9 40.51(12) yes . . .
C8 Fe1 C10 67.95(11) yes . . .
C9 Fe1 C10 40.62(12) yes . . .
O5 N1 O6 123.7(2) yes . . .
O5 N1 C14 118.27(19) yes . . .
O6 N1 C14 118.0(2) yes . . .
I1 C1 Fe1 127.76(11) yes . . .
I1 C1 C2 125.94(15) yes . . .
I1 C1 C5 124.70(15) yes . . .
Fe1 C1 C2 70.20(10) yes . . .
Fe1 C1 C5 70.64(11) yes . . .
C2 C1 C5 109.29(17) yes . . .
Fe1 C2 C1 68.31(11) yes . . .
Fe1 C2 C3 70.03(12) yes . . .
Fe1 C2 C11 127.19(15) yes . . .
C1 C2 C3 106.26(18) yes . . .
C1 C2 C11 126.38(17) yes . . .
C3 C2 C11 127.35(17) yes . . .
Fe1 C3 C2 69.09(12) yes . . .
Fe1 C3 C4 69.63(14) yes . . .
C2 C3 C4 108.67(18) yes . . .
Fe1 C4 C3 69.90(14) yes . . .
Fe1 C4 C5 69.66(13) yes . . .
C3 C4 C5 108.91(19) yes . . .
Fe1 C5 C1 68.22(12) yes . . .
Fe1 C5 C4 69.82(12) yes . . .
C1 C5 C4 106.87(19) yes . . .
Fe1 C6 C7 70.16(16) yes . . .
Fe1 C6 C10 69.81(17) yes . . .
C7 C6 C10 108.2(3) yes . . .
Fe1 C7 C6 69.74(16) yes . . .
Fe1 C7 C8 69.92(15) yes . . .
C6 C7 C8 108.4(3) yes . . .
Fe1 C8 C7 70.03(13) yes . . .
Fe1 C8 C9 69.49(14) yes . . .
C7 C8 C9 108.0(3) yes . . .
Fe1 C9 C8 69.99(15) yes . . .
Fe1 C9 C10 69.74(15) yes . . .
C8 C9 C10 107.6(3) yes . . .
Fe1 C10 C6 69.90(17) yes . . .
Fe1 C10 C9 69.64(16) yes . . .
C6 C10 C9 107.9(3) yes . . .
C2 C11 C12 112.06(16) yes . . .
C2 C11 C14 112.72(17) yes . . .
C12 C11 C14 111.84(17) yes . . .
C11 C12 C13 112.89(16) yes . . .
O1 C13 O4 123.5(2) yes . . .
O1 C13 C12 113.88(18) yes . . .
O4 C13 C12 122.55(18) yes . . .
N1 C14 C11 110.27(16) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 996655'
