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

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#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_lhk-12-5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 Fe N13 O'
_chemical_formula_weight         690.54

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           ?
_symmetry_space_group_name_H-M   p_1_21/n_1

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                   11.734(5)
_cell_length_b                   11.967(5)
_cell_length_c                   12.461(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.528(7)
_cell_angle_gamma                90.00
_cell_volume                     1591.9(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(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          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             714
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_T_max  0.9396
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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            11638
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2767
_reflns_number_gt                1753
_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)+(0.1793P)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_number_reflns         2767
_refine_ls_number_parameters     277
_refine_ls_number_restraints     134
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2637
_refine_ls_wR_factor_gt          0.2326
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.5000 0.5000 0.0416(2) Uani 1 2 d S . .
N1 N 0.3938(3) 0.3665(3) 0.4910(3) 0.0419(8) Uani 1 1 d . A .
N2 N 0.5055(3) 0.5361(3) 0.6575(3) 0.0478(9) Uani 1 1 d . . .
C1 C 0.5723(3) 0.6216(3) 0.7326(3) 0.0441(10) Uani 1 1 d . . .
C2 C 0.5602(4) 0.6143(4) 0.8435(4) 0.0600(13) Uani 1 1 d . . .
H2A H 0.5960 0.6617 0.9081 0.072 Uiso 1 1 calc R . .
C3 C 0.4859(4) 0.5242(4) 0.8344(4) 0.0687(14) Uani 1 1 d . . .
H3A H 0.4594 0.4991 0.8909 0.082 Uiso 1 1 calc R . .
C4 C 0.4565(4) 0.4759(4) 0.7213(4) 0.0596(13) Uani 1 1 d . . .
C5 C 0.3836(4) 0.3783(5) 0.6817(4) 0.0872(17) Uani 1 1 d . . .
C6 C 0.3576(4) 0.3296(4) 0.5734(4) 0.0618(13) Uani 1 1 d . A .
C7 C 0.2832(5) 0.2272(5) 0.5344(4) 0.0816(16) Uani 1 1 d . . .
H7A H 0.2482 0.1859 0.5762 0.098 Uiso 1 1 calc R A .
C8 C 0.2759(4) 0.2052(4) 0.4270(4) 0.0665(14) Uani 1 1 d . . .
H8A H 0.2349 0.1450 0.3794 0.080 Uiso 1 1 calc R . .
C9 C 0.3436(3) 0.2925(3) 0.3985(4) 0.0494(11) Uani 1 1 d . . .
C10 C 0.3580(4) 0.2975(3) 0.2931(3) 0.0477(11) Uani 1 1 d . . .
C11 C 0.2940(4) 0.2094(3) 0.2035(3) 0.0472(11) Uani 1 1 d . . .
C12 C 0.1715(4) 0.1788(4) 0.1526(4) 0.0617(13) Uani 1 1 d . A .
H12A H 0.1077 0.2139 0.1656 0.074 Uiso 1 1 calc R . .
C16 C 0.2670(4) 0.0667(4) 0.0877(5) 0.0694(14) Uani 1 1 d . . .
H16A H 0.2854 0.0080 0.0485 0.083 Uiso 1 1 calc R A .
N6 N 0.1555(3) 0.0899(3) 0.0800(3) 0.0474(9) Uani 1 1 d . . .
N5 N 0.3523(3) 0.1390(3) 0.1600(4) 0.0825(14) Uani 1 1 d . . .
N3 N 0.2755(4) 0.2848(4) 0.7845(4) 0.0916(12) Uani 1 1 d DU . .
C13 C 0.2642(8) 0.2175(9) 0.8598(9) 0.088(2) Uani 0.50 1 d PDU A 1
H13A H 0.1944 0.2002 0.8740 0.106 Uiso 0.50 1 calc PR A 1
C14 C 0.4577(7) 0.2244(9) 0.8634(8) 0.088(3) Uani 0.50 1 d PDU A 1
H14A H 0.5422 0.2111 0.8838 0.106 Uiso 0.50 1 calc PR A 1
C15 C 0.3713(8) 0.2973(7) 0.7727(7) 0.0613(18) Uani 0.50 1 d PDU A 1
N4 N 0.3800(7) 0.1800(8) 0.9113(7) 0.089(2) Uani 0.50 1 d PDU A 1
H4A H 0.4048 0.1329 0.9686 0.107 Uiso 0.50 1 calc PR A 1
O1W O 0.0595(6) 0.4089(8) 0.6022(9) 0.113(3) Uani 0.50 1 d P B 1
N1A N -0.0331(11) 0.5161(12) 0.0205(11) 0.143(4) Uani 0.50 1 d PDU . 1
C2A C -0.0640(16) 0.5489(17) -0.1007(13) 0.143(4) Uani 0.50 1 d PDU . 1
C1A C -0.1145(14) 0.5675(17) 0.0682(17) 0.162(5) Uani 0.50 1 d PDU C 1
C15A C 0.2770(8) 0.3793(10) 0.7414(10) 0.087(2) Uani 0.50 1 d PDU A 2
C14A C 0.1856(8) 0.4408(8) 0.7594(10) 0.106(3) Uani 0.50 1 d PDU A 2
H14B H 0.1686 0.5163 0.7429 0.127 Uiso 0.50 1 calc PR A 2
N4A N 0.1244(9) 0.3701(8) 0.8060(9) 0.114(3) Uani 0.50 1 d PDU A 2
H4AA H 0.0554 0.3820 0.8127 0.137 Uiso 0.50 1 calc PR A 2
C13A C 0.1988(9) 0.2769(10) 0.8391(10) 0.100(3) Uani 0.50 1 d PDU A 2
H13B H 0.1964 0.2201 0.8890 0.120 Uiso 0.50 1 calc PR A 2


_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 N2 1.984(4) . ?
Fe1 N2 1.984(4) 3_666 ?
Fe1 N6 1.993(3) 4_666 ?
Fe1 N6 1.993(3) 2 ?
Fe1 N1 2.000(3) 3_666 ?
Fe1 N1 2.000(3) . ?
N1 C6 1.339(6) . ?
N1 C9 1.378(5) . ?
N2 C4 1.364(6) . ?
N2 C1 1.390(5) . ?
C1 C10 1.388(6) 3_666 ?
C1 C2 1.449(6) . ?
C2 C3 1.361(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.427(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.410(7) . ?
C5 C6 1.382(7) . ?
C5 C15 1.543(9) . ?
C5 C15A 1.700(12) . ?
C6 C7 1.465(7) . ?
C7 C8 1.331(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.443(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.393(6) . ?
C10 C1 1.388(6) 3_666 ?
C10 C11 1.492(5) . ?
C11 N5 1.334(6) . ?
C11 C12 1.359(5) . ?
C12 N6 1.358(5) . ?
C12 H12A 0.9300 . ?
C16 N6 1.302(5) . ?
C16 N5 1.346(6) . ?
C16 H16A 0.9300 . ?
N6 Fe1 1.993(3) 2_545 ?
N3 C15 1.202(9) . ?
N3 C15A 1.255(12) . ?
N3 C13 1.285(10) . ?
N3 C13A 1.338(12) . ?
C13 N4 1.317(10) . ?
C13 H13A 0.9300 . ?
C14 N4 1.385(11) . ?
C14 C15 1.455(11) . ?
C14 H14A 0.9300 . ?
N4 H4A 0.8600 . ?
N1A N1A 1.16(3) 3_565 ?
N1A C2A 1.40(2) 3_565 ?
N1A C1A 1.454(16) . ?
N1A C2A 1.454(15) . ?
C2A N1A 1.40(2) 3_565 ?
C15A C14A 1.394(11) . ?
C14A N4A 1.383(11) . ?
C14A H14B 0.9300 . ?
N4A C13A 1.370(12) . ?
N4A H4AA 0.8600 . ?
C13A H13B 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
N2 Fe1 N2 180.0 . 3_666 ?
N2 Fe1 N6 88.62(13) . 4_666 ?
N2 Fe1 N6 91.38(13) 3_666 4_666 ?
N2 Fe1 N6 91.38(13) . 2 ?
N2 Fe1 N6 88.62(13) 3_666 2 ?
N6 Fe1 N6 180.000(1) 4_666 2 ?
N2 Fe1 N1 90.42(14) . 3_666 ?
N2 Fe1 N1 89.58(14) 3_666 3_666 ?
N6 Fe1 N1 89.06(13) 4_666 3_666 ?
N6 Fe1 N1 90.94(13) 2 3_666 ?
N2 Fe1 N1 89.58(14) . . ?
N2 Fe1 N1 90.42(14) 3_666 . ?
N6 Fe1 N1 90.94(13) 4_666 . ?
N6 Fe1 N1 89.06(13) 2 . ?
N1 Fe1 N1 180.0 3_666 . ?
C6 N1 C9 105.5(3) . . ?
C6 N1 Fe1 127.5(3) . . ?
C9 N1 Fe1 126.9(3) . . ?
C4 N2 C1 104.6(3) . . ?
C4 N2 Fe1 127.8(3) . . ?
C1 N2 Fe1 127.2(3) . . ?
C10 C1 N2 125.4(4) 3_666 . ?
C10 C1 C2 124.3(4) 3_666 . ?
N2 C1 C2 110.3(4) . . ?
C3 C2 C1 106.3(4) . . ?
C3 C2 H2A 126.8 . . ?
C1 C2 H2A 126.8 . . ?
C2 C3 C4 106.7(4) . . ?
C2 C3 H3A 126.6 . . ?
C4 C3 H3A 126.6 . . ?
N2 C4 C5 125.1(4) . . ?
N2 C4 C3 112.0(4) . . ?
C5 C4 C3 123.0(4) . . ?
C6 C5 C4 123.1(5) . . ?
C6 C5 C15 113.7(5) . . ?
C4 C5 C15 119.4(5) . . ?
C6 C5 C15A 121.7(5) . . ?
C4 C5 C15A 106.9(6) . . ?
C15 C5 C15A 51.1(5) . . ?
N1 C6 C5 126.7(4) . . ?
N1 C6 C7 110.8(4) . . ?
C5 C6 C7 122.5(5) . . ?
C8 C7 C6 106.3(5) . . ?
C8 C7 H7A 126.9 . . ?
C6 C7 H7A 126.9 . . ?
C7 C8 C9 107.0(4) . . ?
C7 C8 H8A 126.5 . . ?
C9 C8 H8A 126.5 . . ?
N1 C9 C10 125.7(4) . . ?
N1 C9 C8 110.3(4) . . ?
C10 C9 C8 123.9(4) . . ?
C1 C10 C9 124.2(4) 3_666 . ?
C1 C10 C11 118.7(4) 3_666 . ?
C9 C10 C11 117.1(4) . . ?
N5 C11 C12 105.1(4) . . ?
N5 C11 C10 124.6(4) . . ?
C12 C11 C10 130.2(4) . . ?
C11 C12 N6 110.4(4) . . ?
C11 C12 H12A 124.8 . . ?
N6 C12 H12A 124.8 . . ?
N6 C16 N5 110.9(4) . . ?
N6 C16 H16A 124.5 . . ?
N5 C16 H16A 124.5 . . ?
C16 N6 C12 105.1(3) . . ?
C16 N6 Fe1 127.2(3) . 2_545 ?
C12 N6 Fe1 127.0(3) . 2_545 ?
C11 N5 C16 108.3(4) . . ?
C15 N3 C15A 69.8(6) . . ?
C15 N3 C13 123.6(6) . . ?
C15A N3 C13 154.4(9) . . ?
C15 N3 C13A 158.7(7) . . ?
C15A N3 C13A 114.4(8) . . ?
C13 N3 C13A 44.7(6) . . ?
N3 C13 N4 99.8(7) . . ?
N3 C13 H13A 130.1 . . ?
N4 C13 H13A 130.1 . . ?
N4 C14 C15 101.2(7) . . ?
N4 C14 H14A 129.4 . . ?
C15 C14 H14A 129.4 . . ?
N3 C15 C14 102.4(7) . . ?
N3 C15 C5 123.1(7) . . ?
C14 C15 C5 134.5(7) . . ?
C13 N4 C14 112.9(8) . . ?
C13 N4 H4A 123.5 . . ?
C14 N4 H4A 123.5 . . ?
N1A N1A C2A 68.5(12) 3_565 3_565 ?
N1A N1A C1A 174(2) 3_565 . ?
C2A N1A C1A 115.0(15) 3_565 . ?
N1A N1A C2A 63.6(13) 3_565 . ?
C2A N1A C2A 132.1(12) 3_565 . ?
C1A N1A C2A 112.8(14) . . ?
N1A C2A N1A 47.9(12) 3_565 . ?
N3 C15A C14A 105.0(9) . . ?
N3 C15A C5 109.0(7) . . ?
C14A C15A C5 146.0(10) . . ?
N4A C14A C15A 108.2(9) . . ?
N4A C14A H14B 125.9 . . ?
C15A C14A H14B 125.9 . . ?
C13A N4A C14A 104.3(9) . . ?
C13A N4A H4AA 127.8 . . ?
C14A N4A H4AA 127.8 . . ?
N3 C13A N4A 105.6(9) . . ?
N3 C13A H13B 127.2 . . ?
N4A C13A H13B 127.2 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.125
_database_code_depnum_ccdc_archive 'CCDC 904982'
