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

 
data_160K
 
_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'
 'O'  'O'   0.0106   0.0060
 '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'
 '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            163
_space_group_name_H-M_alt         'P -3 1 c'
_space_group_name_Hall            '-P 3 2c'
 
_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, -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'
 
_cell_length_a                    8.2603(3)
_cell_length_b                    8.2603(3)
_cell_length_c                    13.8466(4)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 120
_cell_volume                      818.20(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     159.97(18)
_cell_measurement_reflns_used   3151
_cell_measurement_theta_min     2.8360
_cell_measurement_theta_max     28.9930
 
_exptl_crystal_description        column
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.737          
_exptl_crystal_F_000              434
_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     1.831
_exptl_absorpt_correction_T_min                   0.88904
_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           0.961
_oxdiff_exptl_absorpt_empirical_full_max           1.088
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature 159.97(18) 
_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             5752
_diffrn_reflns_av_unetI/netI      0.0148
_diffrn_reflns_av_R_equivalents   0.0216
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.847
_diffrn_reflns_theta_max          29.403
_diffrn_reflns_theta_full         28.000
_diffrn_measured_fraction_theta_max   0.939
_diffrn_measured_fraction_theta_full  0.986
_diffrn_reflns_Laue_measured_fraction_max    0.939
_diffrn_reflns_Laue_measured_fraction_full   0.986
_diffrn_reflns_point_group_measured_fraction_max   0.939
_diffrn_reflns_point_group_measured_fraction_full  0.986
_reflns_number_total              723
_reflns_number_gt                 641
_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)+(0.0200P)²+0.5900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          723
_refine_ls_number_parameters      40
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0270
_refine_ls_R_factor_gt            0.0216
_refine_ls_wR_factor_ref          0.0499
_refine_ls_wR_factor_gt           0.0480
_refine_ls_goodness_of_fit_ref    1.041
_refine_ls_restrained_S_all       1.054
_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 0.3333 0.6667 0.2500 0.01184(12) Uani 1 6 d S T P . .
Fe2 Fe 0.0000 1.0000 0.0000 0.01005(12) Uani 1 6 d S T P . .
O1 O 0.11391(15) 0.65801(16) 0.16653(8) 0.0255(3) Uani 1 1 d . . . . .
O2 O -0.01291(14) 0.79341(14) 0.08181(7) 0.0176(2) Uani 1 1 d . . . . .
C1 C 0.1246(2) 0.7889(2) 0.11842(10) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.2428 0.8918 0.1084 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3333 0.6667 0.8673(7) 0.069(3) Uani 0.5 3 d DS T P . .
H2A H 0.4591 0.7698 0.8644 0.104 Uiso 0.1667 1 calc R U P . .
H2B H 0.3224 0.5855 0.9196 0.104 Uiso 0.1667 1 calc R U P . .
H2C H 0.2487 0.7129 0.8775 0.104 Uiso 0.1667 1 calc R U P . .
C21 C 0.3333 0.6667 0.6866(7) 0.069(3) Uani 0.5 3 d DS T P . .
H21A H 0.4621 0.7114 0.6710 0.104 Uiso 0.1667 1 calc R U P . .
H21B H 0.3133 0.7709 0.6939 0.104 Uiso 0.1667 1 calc R U P . .
H21C H 0.2554 0.5872 0.6356 0.104 Uiso 0.1667 1 calc R U P . .
N1 N 0.2870(14) 0.5620(12) 0.7758(4) 0.032(2) Uiso 0.1667 1 d D . P . .
H1A H 0.3442 0.4949 0.7755 0.038 Uiso 0.1667 1 calc R U P . .
H1B H 0.1646 0.4817 0.7755 0.038 Uiso 0.1667 1 calc R U P . .
 
 
_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 O1 2.1205(10) 4_665 ?
Fe1 O1 2.1205(10) 6_565 ?
Fe1 O1 2.1205(10) 3_565 ?
Fe1 O1 2.1205(10) . ?
Fe1 O1 2.1205(10) 2_665 ?
Fe1 O1 2.1205(10) 5 ?
Fe2 O2 2.0061(9) 7_575 ?
Fe2 O2 2.0061(9) . ?
Fe2 O2 2.0062(9) 8_455 ?
Fe2 O2 2.0062(9) 2_675 ?
Fe2 O2 2.0062(9) 9_665 ?
Fe2 O2 2.0062(9) 3_465 ?
O1 C1 1.2349(17) . ?
O2 C1 1.2615(17) . ?
C2 N1 1.473(8) . ?
C21 N1 1.445(8) . ?
 
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
O1 Fe1 O1 93.12(4) 4_665 6_565 ?
O1 Fe1 O1 84.50(6) 4_665 3_565 ?
O1 Fe1 O1 176.66(6) 6_565 3_565 ?
O1 Fe1 O1 89.36(6) 4_665 . ?
O1 Fe1 O1 84.50(6) 6_565 . ?
O1 Fe1 O1 93.12(4) 3_565 . ?
O1 Fe1 O1 176.66(6) 4_665 2_665 ?
O1 Fe1 O1 89.36(6) 6_565 2_665 ?
O1 Fe1 O1 93.12(4) 3_565 2_665 ?
O1 Fe1 O1 93.12(4) . 2_665 ?
O1 Fe1 O1 93.12(4) 4_665 5 ?
O1 Fe1 O1 93.12(4) 6_565 5 ?
O1 Fe1 O1 89.36(6) 3_565 5 ?
O1 Fe1 O1 176.65(6) . 5 ?
O1 Fe1 O1 84.50(6) 2_665 5 ?
O2 Fe2 O2 180.0 7_575 . ?
O2 Fe2 O2 91.25(4) 7_575 8_455 ?
O2 Fe2 O2 88.75(4) . 8_455 ?
O2 Fe2 O2 88.75(4) 7_575 2_675 ?
O2 Fe2 O2 91.25(4) . 2_675 ?
O2 Fe2 O2 180.00(5) 8_455 2_675 ?
O2 Fe2 O2 91.25(4) 7_575 9_665 ?
O2 Fe2 O2 88.75(4) . 9_665 ?
O2 Fe2 O2 91.25(4) 8_455 9_665 ?
O2 Fe2 O2 88.75(4) 2_675 9_665 ?
O2 Fe2 O2 88.75(4) 7_575 3_465 ?
O2 Fe2 O2 91.25(4) . 3_465 ?
O2 Fe2 O2 88.75(4) 8_455 3_465 ?
O2 Fe2 O2 91.25(4) 2_675 3_465 ?
O2 Fe2 O2 180.0 9_665 3_465 ?
C1 O1 Fe1 125.36(10) . . ?
C1 O2 Fe2 125.90(9) . . ?
O1 C1 O2 124.84(14) . . ?
C21 N1 C2 118.1(8) . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N1 H1A O1  0.89 2.43 3.174(9) 141.7 11_666
N1 H1A O1  0.89 2.54 3.241(10) 135.6 8_556
N1 H1B O1  0.89 2.15 2.982(10) 155.8 7_566
C2 H2C O2  0.96 2.59 3.448(2) 149.6 9_666
 
_refine_diff_density_max    0.257
_refine_diff_density_min   -0.283
_refine_diff_density_rms    0.052


