# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_skr80-4
_database_code_depnum_ccdc_archive 'CCDC 1063582'
_audit_update_record             
;
2015-05-06 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;
_audit_creation_date             2014-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Fe N14 O4'
_chemical_formula_sum            'C22 H16 Fe N14 O4'
_chemical_formula_weight         596.34
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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'
'-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                   16.2431(8)
_cell_length_b                   10.5762(3)
_cell_length_c                   14.6113(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.796(4)
_cell_angle_gamma                90
_cell_volume                     2457.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8549
_cell_measurement_temperature    180.15
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_correction_T_min  0.8780
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0540
0 -1 0 0.0440
1 0 0 0.0910
-1 0 0 0.0500
0 0 1 0.1120
2 0 -1 0.1060
0 0 -1 0.1240
-2 0 1 0.0850

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6288
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.582
_diffrn_reflns_theta_min         2.313
_diffrn_ambient_temperature      180.15
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1926
_reflns_number_total             2298
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+2.2288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.42314(4) 0.2500 0.01431(13) Uani 1 2 d S T P . .
O1 O 0.81584(9) 0.58588(16) 0.60841(11) 0.0381(4) Uani 1 1 d . . . . .
O2 O 0.87434(9) 0.41117(17) 0.56489(12) 0.0424(4) Uani 1 1 d . . . . .
N1 N 0.57214(9) 0.29333(15) 0.21239(11) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.64907(9) 0.28393(16) 0.27300(11) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.59332(9) 0.43307(15) 0.35233(10) 0.0154(3) Uani 1 1 d . . . . .
N4 N 0.45926(9) 0.55165(15) 0.32473(11) 0.0170(3) Uani 1 1 d . . . . .
N5 N 0.39094(10) 0.62288(16) 0.32150(12) 0.0224(4) Uani 1 1 d . . . . .
N6 N 0.40496(10) 0.69839(17) 0.39508(12) 0.0274(4) Uani 1 1 d . . . . .
N7 N 0.48229(10) 0.67724(17) 0.44761(12) 0.0245(4) Uani 1 1 d . . . . .
C1 C 0.57288(12) 0.2062(2) 0.14773(14) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.5277 0.1897 0.0966 0.030 Uiso 1 1 calc R . . . .
C2 C 0.64993(14) 0.1418(2) 0.16542(15) 0.0322(5) Uani 1 1 d . . . . .
H2 H 0.6663 0.0757 0.1289 0.039 Uiso 1 1 calc R . . . .
C3 C 0.69678(12) 0.1922(2) 0.24489(15) 0.0273(5) Uani 1 1 d . . . . .
H3 H 0.7520 0.1679 0.2748 0.033 Uiso 1 1 calc R . . . .
C4 C 0.66169(11) 0.36335(17) 0.35141(13) 0.0158(4) Uani 1 1 d . . . . .
C5 C 0.73481(11) 0.37433(18) 0.41846(13) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.7823 0.3224 0.4175 0.023 Uiso 1 1 calc R . . . .
C6 C 0.73543(11) 0.46511(18) 0.48741(13) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.66505(11) 0.54004(19) 0.48887(14) 0.0205(4) Uani 1 1 d . . . . .
H7 H 0.6658 0.6023 0.5359 0.025 Uiso 1 1 calc R . . . .
C8 C 0.59433(11) 0.52098(18) 0.42001(13) 0.0169(4) Uani 1 1 d . . . . .
C9 C 0.51370(11) 0.58665(18) 0.40255(13) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.81596(12) 0.4820(2) 0.55746(14) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.89360(16) 0.6138(3) 0.67338(19) 0.0471(7) Uani 1 1 d . . . . .
H11A H 0.9396 0.6190 0.6394 0.071 Uiso 1 1 calc GR . . . .
H11B H 0.9056 0.5466 0.7204 0.071 Uiso 1 1 calc GR . . . .
H11C H 0.8883 0.6947 0.7043 0.071 Uiso 1 1 calc GR . . . .


_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 N1 1.9554(16) 2_655 ?
Fe1 N1 1.9553(16) . ?
Fe1 N3 1.9020(15) . ?
Fe1 N3 1.9020(15) 2_655 ?
Fe1 N4 1.9423(16) . ?
Fe1 N4 1.9423(16) 2_655 ?
O1 C10 1.327(3) . ?
O1 C11 1.447(3) . ?
O2 C10 1.196(3) . ?
N1 N2 1.380(2) . ?
N1 C1 1.321(3) . ?
N2 C3 1.357(2) . ?
N2 C4 1.401(2) . ?
N3 C4 1.335(2) . ?
N3 C8 1.355(2) . ?
N4 N5 1.334(2) . ?
N4 C9 1.342(2) . ?
N5 N6 1.321(2) . ?
N6 N7 1.350(2) . ?
N7 C9 1.322(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.360(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 C7 1.395(3) . ?
C6 C10 1.498(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 C9 1.458(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
N1 Fe1 N1 90.80(9) . 2_655 ?
N3 Fe1 N1 104.17(6) . 2_655 ?
N3 Fe1 N1 80.36(6) 2_655 2_655 ?
N3 Fe1 N1 80.36(6) . . ?
N3 Fe1 N1 104.17(6) 2_655 . ?
N3 Fe1 N3 173.68(10) . 2_655 ?
N3 Fe1 N4 80.09(6) 2_655 2_655 ?
N3 Fe1 N4 95.45(6) . 2_655 ?
N3 Fe1 N4 80.09(6) . . ?
N3 Fe1 N4 95.45(6) 2_655 . ?
N4 Fe1 N1 92.33(6) . 2_655 ?
N4 Fe1 N1 160.38(6) 2_655 2_655 ?
N4 Fe1 N1 160.38(6) . . ?
N4 Fe1 N1 92.33(6) 2_655 . ?
N4 Fe1 N4 91.19(9) . 2_655 ?
C10 O1 C11 115.84(18) . . ?
N2 N1 Fe1 112.73(11) . . ?
C1 N1 Fe1 141.64(13) . . ?
C1 N1 N2 105.62(15) . . ?
N1 N2 C4 116.33(14) . . ?
C3 N2 N1 110.83(16) . . ?
C3 N2 C4 132.76(16) . . ?
C4 N3 Fe1 119.50(12) . . ?
C4 N3 C8 120.01(16) . . ?
C8 N3 Fe1 120.02(12) . . ?
N5 N4 Fe1 138.74(13) . . ?
N5 N4 C9 105.87(15) . . ?
C9 N4 Fe1 115.35(12) . . ?
N6 N5 N4 107.98(15) . . ?
N5 N6 N7 110.37(15) . . ?
C9 N7 N6 104.23(16) . . ?
N1 C1 H1 124.9 . . ?
N1 C1 C2 110.21(18) . . ?
C2 C1 H1 124.9 . . ?
C1 C2 H2 126.6 . . ?
C3 C2 C1 106.83(18) . . ?
C3 C2 H2 126.6 . . ?
N2 C3 C2 106.50(17) . . ?
N2 C3 H3 126.8 . . ?
C2 C3 H3 126.8 . . ?
N3 C4 N2 110.86(15) . . ?
N3 C4 C5 122.86(17) . . ?
C5 C4 N2 126.24(16) . . ?
C4 C5 H5 121.6 . . ?
C4 C5 C6 116.73(17) . . ?
C6 C5 H5 121.6 . . ?
C5 C6 C7 121.26(17) . . ?
C5 C6 C10 116.97(17) . . ?
C7 C6 C10 121.73(18) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 117.97(18) . . ?
C8 C7 H7 121.0 . . ?
N3 C8 C7 121.14(17) . . ?
N3 C8 C9 108.83(16) . . ?
C7 C8 C9 129.99(18) . . ?
N4 C9 C8 115.43(16) . . ?
N7 C9 N4 111.55(16) . . ?
N7 C9 C8 133.01(17) . . ?
O1 C10 C6 112.38(17) . . ?
O2 C10 O1 124.03(18) . . ?
O2 C10 C6 123.57(19) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N1 N2 C3 179.43(13) . . . . ?
Fe1 N1 N2 C4 2.21(19) . . . . ?
Fe1 N1 C1 C2 -179.08(17) . . . . ?
Fe1 N3 C4 N2 -4.3(2) . . . . ?
Fe1 N3 C4 C5 173.56(14) . . . . ?
Fe1 N3 C8 C7 -172.34(14) . . . . ?
Fe1 N3 C8 C9 5.5(2) . . . . ?
Fe1 N4 N5 N6 -177.15(15) . . . . ?
Fe1 N4 C9 N7 177.85(13) . . . . ?
Fe1 N4 C9 C8 -1.2(2) . . . . ?
N1 N2 C3 C2 -0.1(2) . . . . ?
N1 N2 C4 N3 1.2(2) . . . . ?
N1 N2 C4 C5 -176.64(17) . . . . ?
N1 C1 C2 C3 0.7(3) . . . . ?
N2 N1 C1 C2 -0.7(2) . . . . ?
N2 C4 C5 C6 175.97(18) . . . . ?
N3 C4 C5 C6 -1.6(3) . . . . ?
N3 C8 C9 N4 -2.5(2) . . . . ?
N3 C8 C9 N7 178.6(2) . . . . ?
N4 N5 N6 N7 -0.3(2) . . . . ?
N5 N4 C9 N7 -0.4(2) . . . . ?
N5 N4 C9 C8 -179.44(15) . . . . ?
N5 N6 N7 C9 0.1(2) . . . . ?
N6 N7 C9 N4 0.2(2) . . . . ?
N6 N7 C9 C8 179.0(2) . . . . ?
C1 N1 N2 C3 0.5(2) . . . . ?
C1 N1 N2 C4 -176.69(16) . . . . ?
C1 C2 C3 N2 -0.3(3) . . . . ?
C3 N2 C4 N3 -175.3(2) . . . . ?
C3 N2 C4 C5 6.9(3) . . . . ?
C4 N2 C3 C2 176.5(2) . . . . ?
C4 N3 C8 C7 -0.2(3) . . . . ?
C4 N3 C8 C9 177.65(16) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C10 -176.98(17) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C10 O1 167.55(18) . . . . ?
C5 C6 C10 O2 -10.8(3) . . . . ?
C6 C7 C8 N3 -0.6(3) . . . . ?
C6 C7 C8 C9 -177.99(18) . . . . ?
C7 C6 C10 O1 -10.1(3) . . . . ?
C7 C6 C10 O2 171.5(2) . . . . ?
C7 C8 C9 N4 175.05(19) . . . . ?
C7 C8 C9 N7 -3.8(4) . . . . ?
C8 N3 C4 N2 -176.52(15) . . . . ?
C8 N3 C4 C5 1.4(3) . . . . ?
C9 N4 N5 N6 0.4(2) . . . . ?
C10 C6 C7 C8 177.93(17) . . . . ?
C11 O1 C10 O2 2.5(3) . . . . ?
C11 O1 C10 C6 -175.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       'Magnetic properties, Luminescent'
