# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

 
data_100K
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
  'C8 H14 Fe2 N O12' 
_chemical_formula_weight          427.91

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'
 
_space_group_crystal_system       trigonal
_space_group_IT_number            167
_space_group_name_H-M_alt         'R -3 c :H'
_space_group_name_Hall            '-R 3 2"c'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-y, x-y, z'
 '-x+y, -x, z'
 'y, x, -z+1/2'
 'x-y, -y, -z+1/2'
 '-x, -x+y, -z+1/2'
 'x+2/3, y+1/3, z+1/3'
 '-y+2/3, x-y+1/3, z+1/3'
 '-x+y+2/3, -x+1/3, z+1/3'
 'y+2/3, x+1/3, -z+5/6'
 'x-y+2/3, -y+1/3, -z+5/6'
 '-x+2/3, -x+y+1/3, -z+5/6'
 'x+1/3, y+2/3, z+2/3'
 '-y+1/3, x-y+2/3, z+2/3'
 '-x+y+1/3, -x+2/3, z+2/3'
 'y+1/3, x+2/3, -z+7/6'
 'x-y+1/3, -y+2/3, -z+7/6'
 '-x+1/3, -x+y+2/3, -z+7/6'
 '-x, -y, -z'
 'y, -x+y, -z'
 'x-y, x, -z'
 '-y, -x, z-1/2'
 '-x+y, y, z-1/2'
 'x, x-y, z-1/2'
 '-x+2/3, -y+1/3, -z+1/3'
 'y+2/3, -x+y+1/3, -z+1/3'
 'x-y+2/3, x+1/3, -z+1/3'
 '-y+2/3, -x+1/3, z-1/6'
 '-x+y+2/3, y+1/3, z-1/6'
 'x+2/3, x-y+1/3, z-1/6'
 '-x+1/3, -y+2/3, -z+2/3'
 'y+1/3, -x+y+2/3, -z+2/3'
 'x-y+1/3, x+2/3, -z+2/3'
 '-y+1/3, -x+2/3, z+1/6'
 '-x+y+1/3, y+2/3, z+1/6'
 'x+1/3, x-y+2/3, z+1/6'
 
_cell_length_a                    14.2916(5)
_cell_length_b                    14.2916(5)
_cell_length_c                    41.4795(17)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 120
_cell_volume                      7337.1(6)
_cell_formula_units_Z             18
_cell_measurement_temperature     100.0(3)
_cell_measurement_reflns_used   4547
_cell_measurement_theta_min     2.8460
_cell_measurement_theta_max     28.9980
 
_exptl_crystal_description        column
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.743          
_exptl_crystal_F_000              3906
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_absorpt_coefficient_mu     1.838
_exptl_absorpt_correction_T_min                   0.90208
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min           0.963
_oxdiff_exptl_absorpt_empirical_full_max           1.072
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature 100.0(3) 
_diffrn_ambient_environment N~2~
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Atlas'
_diffrn_detector 'CCD plate'
_diffrn_detector_type Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number             15149
_diffrn_reflns_av_unetI/netI      0.0168
_diffrn_reflns_av_R_equivalents   0.0312
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -49
_diffrn_reflns_limit_l_max        50
_diffrn_reflns_theta_min          2.562
_diffrn_reflns_theta_max          25.679
_diffrn_reflns_theta_full         25.679
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              1558
_reflns_number_gt                 1297
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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.
;
 
_computing_data_collection     'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement     'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction      'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1558
_refine_ls_number_parameters      113
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0347
_refine_ls_R_factor_gt            0.0246
_refine_ls_wR_factor_ref          0.0704
_refine_ls_wR_factor_gt           0.0656
_refine_ls_goodness_of_fit_ref    0.984
_refine_ls_restrained_S_all       0.983
_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_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 -0.00721(2) 0.3333 0.0833 0.00759(14) Uani 1 2 d S T P . .
Fe2 Fe 0.0000 0.0000 0.0000 0.00656(16) Uani 1 6 d S T P . .
Fe3 Fe -0.3333 0.3333 -0.00259(2) 0.00686(14) Uani 1 3 d S T P . .
O1 O 0.05888(9) 0.47776(9) 0.05491(3) 0.0135(3) Uani 1 1 d . . . . .
O2 O -0.15582(10) 0.25295(9) 0.05745(3) 0.0134(3) Uani 1 1 d . . . . .
O3 O -0.19873(9) 0.39114(9) -0.02896(2) 0.0107(3) Uani 1 1 d . . . . .
O4 O 0.06326(9) 0.26548(9) 0.05435(3) 0.0148(3) Uani 1 1 d . . . . .
O5 O -0.27945(9) 0.25565(9) 0.02592(2) 0.0111(3) Uani 1 1 d . . . . .
O6 O 0.06712(9) 0.13435(9) 0.02712(3) 0.0116(3) Uani 1 1 d . . . . .
C1 C 0.01846(15) 0.17875(13) 0.03964(4) 0.0123(4) Uani 1 1 d . . . . .
H1 H -0.0563 0.1436 0.0376 0.015 Uiso 1 1 calc R U . . .
C2 C -0.18513(14) 0.29802(15) 0.03735(4) 0.0122(4) Uani 1 1 d . . . . .
H2 H -0.1345 0.3669 0.0304 0.015 Uiso 1 1 calc R U . . .
C3 C 0.14795(14) 0.51540(14) 0.04117(4) 0.0123(4) Uani 1 1 d . . . . .
H3 H 0.1792 0.4719 0.0398 0.015 Uiso 1 1 calc R U . . .
N11B N -0.0450(5) 0.6152(5) 0.07199(17) 0.0124(8) Uiso 0.277(5) 1 d D . P A 1
H11A H -0.0459 0.5526 0.0729 0.015 Uiso 0.277(5) 1 calc R U P A 1
H11B H -0.1128 0.6013 0.0738 0.015 Uiso 0.277(5) 1 calc R U P A 1
C10A C 0.0178(6) 0.6826(6) 0.0990(2) 0.021(2) Uiso 0.277(5) 1 d D . P A 1
H10A H 0.0862 0.6851 0.0999 0.032 Uiso 0.277(5) 1 calc R U P A 1
H10B H -0.0209 0.6527 0.1187 0.032 Uiso 0.277(5) 1 calc R U P A 1
H10C H 0.0296 0.7543 0.0962 0.032 Uiso 0.277(5) 1 calc R U P A 1
C10B C -0.0029(5) 0.6648(5) 0.0409(2) 0.0118(19) Uiso 0.277(5) 1 d D . P A 1
H10D H -0.0071 0.7296 0.0390 0.018 Uiso 0.277(5) 1 calc R U P A 1
H10E H -0.0447 0.6154 0.0240 0.018 Uiso 0.277(5) 1 calc R U P A 1
H10F H 0.0711 0.6824 0.0390 0.018 Uiso 0.277(5) 1 calc R U P A 1
N1 N -0.0517(4) 0.6150(4) 0.0833 0.0124(8) Uiso 0.445(11) 2 d DS . P A 2
H1A H -0.1174 0.6073 0.0835 0.015 Uiso 0.223(5) 1 calc R U P A 2
H1B H -0.0593 0.5492 0.0832 0.015 Uiso 0.223(5) 1 calc R U P A 2
C12 C 0.0042(4) 0.6717(4) 0.05427(16) 0.0199(15) Uiso 0.445(11) 1 d D . P A 2
H12A H 0.0144 0.7434 0.0546 0.030 Uiso 0.445(11) 1 calc R U P A 2
H12B H -0.0380 0.6335 0.0358 0.030 Uiso 0.445(11) 1 calc R U P A 2
H12C H 0.0732 0.6757 0.0532 0.030 Uiso 0.445(11) 1 calc R U P 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 O4 2.0919(12) 17_554 ?
Fe1 O4 2.0920(12) . ?
Fe1 O2 2.1315(12) 17_554 ?
Fe1 O2 2.1315(12) . ?
Fe1 O1 2.1431(11) 17_554 ?
Fe1 O1 2.1432(11) . ?
Fe2 O6 2.0076(11) 21 ?
Fe2 O6 2.0076(11) 3 ?
Fe2 O6 2.0076(11) . ?
Fe2 O6 2.0077(11) 19 ?
Fe2 O6 2.0077(11) 2 ?
Fe2 O6 2.0077(11) 20 ?
Fe3 O3 1.9974(11) 3_455 ?
Fe3 O3 1.9974(11) 2_565 ?
Fe3 O3 1.9974(11) . ?
Fe3 O5 2.0199(11) . ?
Fe3 O5 2.0200(11) 2_565 ?
Fe3 O5 2.0200(11) 3_455 ?
O1 C3 1.245(2) . ?
O2 C2 1.2470(19) . ?
O3 C3 1.2641(19) 19_565 ?
O4 C1 1.235(2) . ?
O5 C2 1.2618(19) . ?
O6 C1 1.2638(19) . ?
C3 O3 1.2641(19) 19_565 ?
N11B C10B 1.451(7) . ?
N11B C10A 1.457(7) . ?
N1 C12 1.449(6) 16_454 ?
N1 C12 1.449(6) . ?
 
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
O4 Fe1 O4 89.01(6) 17_554 . ?
O4 Fe1 O2 92.39(4) 17_554 17_554 ?
O4 Fe1 O2 174.42(4) . 17_554 ?
O4 Fe1 O2 174.42(4) 17_554 . ?
O4 Fe1 O2 92.39(4) . . ?
O2 Fe1 O2 86.74(6) 17_554 . ?
O4 Fe1 O1 92.74(4) 17_554 17_554 ?
O4 Fe1 O1 90.60(5) . 17_554 ?
O2 Fe1 O1 94.73(4) 17_554 17_554 ?
O2 Fe1 O1 81.84(5) . 17_554 ?
O4 Fe1 O1 90.60(5) 17_554 . ?
O4 Fe1 O1 92.74(4) . . ?
O2 Fe1 O1 81.84(5) 17_554 . ?
O2 Fe1 O1 94.73(4) . . ?
O1 Fe1 O1 175.32(6) 17_554 . ?
O6 Fe2 O6 180.00(7) 21 3 ?
O6 Fe2 O6 88.34(4) 21 . ?
O6 Fe2 O6 91.66(4) 3 . ?
O6 Fe2 O6 91.66(4) 21 19 ?
O6 Fe2 O6 88.34(4) 3 19 ?
O6 Fe2 O6 180.0 . 19 ?
O6 Fe2 O6 88.34(4) 21 2 ?
O6 Fe2 O6 91.66(4) 3 2 ?
O6 Fe2 O6 91.66(4) . 2 ?
O6 Fe2 O6 88.34(4) 19 2 ?
O6 Fe2 O6 91.66(4) 21 20 ?
O6 Fe2 O6 88.34(4) 3 20 ?
O6 Fe2 O6 88.34(4) . 20 ?
O6 Fe2 O6 91.66(4) 19 20 ?
O6 Fe2 O6 180.00(7) 2 20 ?
O3 Fe3 O3 92.90(4) 3_455 2_565 ?
O3 Fe3 O3 92.89(4) 3_455 . ?
O3 Fe3 O3 92.89(4) 2_565 . ?
O3 Fe3 O5 88.17(5) 3_455 . ?
O3 Fe3 O5 177.13(4) 2_565 . ?
O3 Fe3 O5 89.71(5) . . ?
O3 Fe3 O5 177.13(4) 3_455 2_565 ?
O3 Fe3 O5 89.71(5) 2_565 2_565 ?
O3 Fe3 O5 88.17(5) . 2_565 ?
O5 Fe3 O5 89.17(5) . 2_565 ?
O3 Fe3 O5 89.71(5) 3_455 3_455 ?
O3 Fe3 O5 88.17(5) 2_565 3_455 ?
O3 Fe3 O5 177.13(4) . 3_455 ?
O5 Fe3 O5 89.17(5) . 3_455 ?
O5 Fe3 O5 89.17(5) 2_565 3_455 ?
C3 O1 Fe1 122.07(11) . . ?
C2 O2 Fe1 124.05(11) . . ?
C3 O3 Fe3 125.58(11) 19_565 . ?
C1 O4 Fe1 128.39(11) . . ?
C2 O5 Fe3 124.44(11) . . ?
C1 O6 Fe2 126.20(11) . . ?
O4 C1 O6 124.58(17) . . ?
O2 C2 O5 123.87(17) . . ?
O1 C3 O3 124.25(17) . 19_565 ?
C10B N11B C10A 113.1(6) . . ?
C12 N1 C12 112.6(6) 16_454 . ?
 
_refine_diff_density_max    0.244
_refine_diff_density_min   -0.342
_refine_diff_density_rms    0.055



