# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_sx899b
_database_code_depnum_ccdc_archive 'CCDC 2095300'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica Yrezabal'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 Fe N4'
_chemical_formula_sum            'C10 H11 Fe N4'
_chemical_formula_weight         243.08
_chemical_absolute_configuration ad
_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'

_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      cubic
_space_group_IT_number           217
_space_group_name_H-M_alt        'I -4 3 m'
_space_group_name_Hall           'I -4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, z'
'-y, -x, z'
'y, -x, -z'
'-y, x, -z'
'x, z, y'
'-x, z, -y'
'-x, -z, y'
'x, -z, -y'
'z, y, x'
'z, -y, -x'
'-z, y, -x'
'-z, -y, x'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1/2, -x+1/2, -y+1/2'
'-z+1/2, -x+1/2, y+1/2'
'-z+1/2, x+1/2, -y+1/2'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x+1/2'
'-y+1/2, -z+1/2, x+1/2'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, z+1/2, y+1/2'
'-x+1/2, z+1/2, -y+1/2'
'-x+1/2, -z+1/2, y+1/2'
'x+1/2, -z+1/2, -y+1/2'
'z+1/2, y+1/2, x+1/2'
'z+1/2, -y+1/2, -x+1/2'
'-z+1/2, y+1/2, -x+1/2'
'-z+1/2, -y+1/2, x+1/2'

_cell_length_a                   17.1728(6)
_cell_length_b                   17.1728(6)
_cell_length_c                   17.1728(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5064.3(6)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1902
_cell_measurement_temperature    119.5(8)
_cell_measurement_theta_max      16.8580
_cell_measurement_theta_min      3.3440
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.956
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1500
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1646
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.965
_diffrn_reflns_theta_max         24.965
_diffrn_reflns_theta_min         2.905
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.5(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0267
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  15.00   1.00   30.00    --  -14.89 -77.00  30.00   57
  2  ω    -41.00  15.00   1.00   30.00    --  -14.89 -77.00 -60.00   56
  3  ω    -88.00  56.00   1.00   30.00    --  -14.89   0.00-120.00  144
  4  ω    -74.00 -35.00   1.00   30.00    --  -14.89 127.00-153.39   39
  5  ω    -40.00  58.00   1.00   30.00    --  -14.89  38.00 -60.00   98
  6  ω     -6.00  85.00   1.00   30.00    --   15.83  57.00-180.00   91
  7  ω     -4.00  85.00   1.00   30.00    --   15.83  57.00 -90.00   89
  8  ω    -27.00  46.00   1.00   30.00    --   15.83 -77.00  30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0403714000
_diffrn_orient_matrix_UB_12      0.0023788000
_diffrn_orient_matrix_UB_13      0.0084555000
_diffrn_orient_matrix_UB_21      0.0067567000
_diffrn_orient_matrix_UB_22      -0.0168148000
_diffrn_orient_matrix_UB_23      0.0371694000
_diffrn_orient_matrix_UB_31      0.0055937000
_diffrn_orient_matrix_UB_32      0.0375557000
_diffrn_orient_matrix_UB_33      0.0161044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                637
_reflns_number_total             863
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         863
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.046
_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)+(0.0623P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1187
_refine_special_details          
'Refined as a 2-component inversion twin.,Twin,SQUEEZE'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.88(8)
 0.12(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C3-C5 = C6-C5
 1.39 with sigma of 0.002
 C6_$2-C6_$3
 1.39 with sigma of 0.02
4. Restrained planarity
 C3, C3_$1, C5_$1, C6_$1, C6, C5
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
6. Rigid body (RIGU) restrains
 C4, C2, N1, C3, C5, C6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
7. Others
 Fixed Sof: H3(0.75) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5) C6(0.25) H6(0.25)
 C5(0.25) H5(0.25)
8.a Riding coordinates:
 C6(H6)
8.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
8.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 -0.500000 -0.250000 -1.000000 0.0684(7) Uani 1 4 d S T P . .
C2 C -0.6241(3) -0.3759(3) -0.9963(7) 0.059(2) Uani 1 2 d S T P . .
N1 N -0.5847(3) -0.3233(3) -1.0395(3) 0.0708(15) Uani 1 1 d . . . . .
C3 C -0.6146(4) -0.3289(5) -1.1141(4) 0.084(2) Uani 1 1 d D . . . .
H3 H -0.599093 -0.299468 -1.156791 0.100 Uiso 0.75 1 calc R U P A 2
C4 C -0.613(2) -0.3965(19) -0.9158(6) 0.078(7) Uani 0.5 1 d . . P B -1
H4A H -0.644850 -0.441174 -0.903713 0.117 Uiso 0.5 1 calc R U P B -1
H4B H -0.628841 -0.353628 -0.883393 0.117 Uiso 0.5 1 calc R U P B -1
H4C H -0.559662 -0.408490 -0.906587 0.117 Uiso 0.5 1 calc R U P B -1
C6 C -0.6252(9) -0.3178(8) -1.2554(10) 0.049(5) Uani 0.25 1 d D U P C -1
H6 H -0.615450 -0.289418 -1.300501 0.058 Uiso 0.25 1 d R U P C -1
C5 C -0.5883(10) -0.3010(11) -1.1854(6) 0.071(7) Uani 0.25 1 d D U P C -1
H5 H -0.544102 -0.269814 -1.186251 0.085 Uiso 0.25 1 calc R U P C -1


_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 2.040(6) . ?
Fe1 N1 2.040(6) 48_344 ?
Fe1 N1 2.040(6) 46_543 ?
Fe1 N1 2.040(6) 3_453 ?
C2 N1 1.350(7) 14_445 ?
C2 N1 1.350(7) . ?
C2 C4 1.438(15) . ?
N1 C3 1.383(7) . ?
C3 C3 1.372(15) 14_445 ?
C3 H3 0.9300 . ?
C3 C5 1.390(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C6 1.38(2) 14_445 ?
C6 H6 0.9299 . ?
C6 C5 1.389(3) . ?
C5 H5 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
N1 Fe1 N1 112.38(15) . 46_543 ?
N1 Fe1 N1 103.8(3) 46_543 48_344 ?
N1 Fe1 N1 112.38(15) 46_543 3_453 ?
N1 Fe1 N1 112.38(15) 48_344 3_453 ?
N1 Fe1 N1 103.8(3) . 3_453 ?
N1 Fe1 N1 112.38(15) . 48_344 ?
N1 C2 N1 111.6(10) 14_445 . ?
N1 C2 C4 119(2) 14_445 . ?
N1 C2 C4 129(2) . . ?
C2 N1 Fe1 126.0(5) . . ?
C2 N1 C3 106.1(7) . . ?
C3 N1 Fe1 128.0(5) . . ?
N1 C3 H3 125.9 . . ?
N1 C3 C5 132.2(9) . . ?
C3 C3 N1 108.1(4) 14_445 . ?
C3 C3 H3 125.9 14_445 . ?
C3 C3 C5 118.2(8) 14_445 . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C6 H6 119.9 14_445 . ?
C6 C6 C5 117.9(8) 14_445 . ?
C5 C6 H6 122.0 . . ?
C3 C5 H5 118.5 . . ?
C6 C5 C3 122.9(15) . . ?
C6 C5 H5 118.5 . . ?

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 C3 C3 -179.4(3) . . . 14_445 ?
Fe1 N1 C3 C5 15.0(16) . . . . ?
C2 N1 C3 C3 -0.4(5) . . . 14_445 ?
C2 N1 C3 C5 -166.1(14) . . . . ?
N1 C2 N1 Fe1 179.7(2) 14_445 . . . ?
N1 C2 N1 C3 0.8(8) 14_445 . . . ?
N1 C3 C5 C6 175.6(13) . . . . ?
C3 C3 C5 C6 11(2) 14_445 . . . ?
C4 C2 N1 Fe1 -4.3(11) . . . . ?
C4 C2 N1 C3 176.7(9) . . . . ?
C6 C6 C5 C3 -11(2) 14_445 . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 474 electrons were 
found in a volume of 1804Å³ in 1 void per unit cell. 
This is consistent with the presence of 
4[H2O] per Asymmetric Unit 
which account for 480 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 901.5 236.6 '24 water'
2 0.000 0.000 0.500 8.8 0.0 ?
3 0.000 0.500 0.000 8.8 0.0 ?
4 0.000 0.500 0.500 8.8 0.0 ?
5 0.500 0.500 0.500 901.5 236.6 '24 water'
6 0.500 0.000 0.000 8.8 0.0 ?
7 0.500 0.000 0.500 8.8 0.0 ?
8 0.500 0.500 0.000 8.8 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.112
_oxdiff_exptl_absorpt_empirical_full_min 0.943
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.88(8)
2 0.12(8)

####################################################################### 
# 
# 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_sx831
_database_code_depnum_ccdc_archive 'CCDC 2095301'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica Yrezabal'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 Fe N4, 4[H2O]'
_chemical_formula_sum            'C12 H14 Fe N4'
_chemical_formula_weight         270.12
_chemical_absolute_configuration ad
_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'

_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      cubic
_space_group_IT_number           217
_space_group_name_H-M_alt        'I -4 3 m'
_space_group_name_Hall           'I -4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, z'
'-y, -x, z'
'y, -x, -z'
'-y, x, -z'
'x, z, y'
'-x, z, -y'
'-x, -z, y'
'x, -z, -y'
'z, y, x'
'z, -y, -x'
'-z, y, -x'
'-z, -y, x'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1/2, -x+1/2, -y+1/2'
'-z+1/2, -x+1/2, y+1/2'
'-z+1/2, x+1/2, -y+1/2'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x+1/2'
'-y+1/2, -z+1/2, x+1/2'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, z+1/2, y+1/2'
'-x+1/2, z+1/2, -y+1/2'
'-x+1/2, -z+1/2, y+1/2'
'x+1/2, -z+1/2, -y+1/2'
'z+1/2, y+1/2, x+1/2'
'z+1/2, -y+1/2, -x+1/2'
'-z+1/2, y+1/2, -x+1/2'
'-z+1/2, -y+1/2, x+1/2'

_cell_length_a                   17.31700(10)
_cell_length_b                   17.31700(10)
_cell_length_c                   17.31700(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5193.00(9)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    12309
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      23.0420
_cell_measurement_theta_min      4.0640
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33960
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.960
_diffrn_reflns_theta_min         3.327
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0267
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  12.00   1.00   20.00    --  -14.89 -80.00  59.00   53
  2  ω    -30.00  53.00   1.00   20.00    --  -14.89  38.00 -90.00   83
  3  ω     -6.00  85.00   1.00   20.00    --   15.83  57.00 -60.00   91
  4  ω    -53.00  30.00   1.00   20.00    --   15.83 -57.00  30.00   83
  5  ω      1.00  85.00   1.00   20.00    --   15.83  57.00  30.00   84
  6  ω     39.00  71.00   1.00   20.00    --   15.83 178.00  60.00   32
  7  ω     -3.00  85.00   1.00   20.00    --   15.83  57.00-180.00   88
  8  ω    -42.00  46.00   1.00   20.00    --   15.83 -77.00 150.00   88
  9  ω     33.00  58.00   1.00   20.00    --   15.83 -99.00  60.00   25
 10  ω     41.00  76.00   1.00   20.00    --   15.83-129.00 -37.38   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0020559000
_diffrn_orient_matrix_UB_12      -0.0183244000
_diffrn_orient_matrix_UB_13      0.0365479000
_diffrn_orient_matrix_UB_21      -0.0241439000
_diffrn_orient_matrix_UB_22      0.0301183000
_diffrn_orient_matrix_UB_23      0.0137372000
_diffrn_orient_matrix_UB_31      -0.0330605000
_diffrn_orient_matrix_UB_32      -0.0208260000
_diffrn_orient_matrix_UB_33      -0.0123228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                917
_reflns_number_total             1169
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.16(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1169
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.023
_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)+(0.0586P)²+1.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          
'Refined as a 2-component inversion twin.,Twin,SQUEEZE'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.84(4)
 0.16(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Shared sites
{C1, C1A}
4. Restrained planarity
 C2, N1, C3, C5, C6
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C1) = Uanis(C1A)
Uanis(C1A) = Uanis(C1)
6. Others
 Fixed Sof: H3(0.6667) C5(0.33333) H5(0.33333) C6(0.33333) H6(0.33333)
 C1(0.33335) H1A(0.33335) H1B(0.33335) C4(0.33335) H4A(0.33335) H4B(0.33335)
 H4C(0.33335) C1A(0.16665) H1AA(0.16665) H1AB(0.16665) H1AC(0.16665)
7.a Riding coordinates:
 C6(H6)
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
7.c Me refined with riding coordinates:
 C1A(H1AA,H1AB,H1AC)
7.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
7.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.500000 0.250000 1.000000 0.0565(3) Uani 1 4 d S T P . .
N1 N 0.58646(19) 0.32176(16) 1.03487(17) 0.0568(7) Uani 1 1 d . . . . .
C2 C 0.62517(18) 0.37483(18) 0.9906(3) 0.0511(11) Uani 1 2 d S T P . .
C3 C 0.6169(2) 0.3288(2) 1.1085(2) 0.0651(9) Uani 1 1 d . . . . .
H3 H 0.601696 0.299996 1.151224 0.078 Uiso 0.6667 1 calc R U P A 2
C5 C 0.5891(5) 0.2885(7) 1.1935(7) 0.058(3) Uani 0.3333 1 d . U P B -1
H5 H 0.551109 0.250665 1.196157 0.070 Uiso 0.3333 1 calc R U P B -1
C6 C 0.6281(6) 0.3166(7) 1.2610(6) 0.064(3) Uani 0.3333 1 d . U P B -1
H6 H 0.613013 0.292682 1.306628 0.077 Uiso 0.3333 1 d R U P B -1
C1 C 0.605(3) 0.387(3) 0.9111(4) 0.082(6) Uani 0.3334 1 d . . P C -1
H1A H 0.588454 0.338882 0.888553 0.098 Uiso 0.3334 1 calc R U P C -1
H1B H 0.650678 0.404465 0.883247 0.098 Uiso 0.3334 1 calc R U P C -1
C4 C 0.5365(16) 0.4517(10) 0.9011(11) 0.129(9) Uani 0.3334 1 d . . P C -1
H4A H 0.544894 0.480494 0.854498 0.193 Uiso 0.3334 1 calc R U P C -1
H4B H 0.537067 0.486159 0.944509 0.193 Uiso 0.3334 1 calc R U P C -1
H4C H 0.487462 0.426045 0.898454 0.193 Uiso 0.3334 1 calc R U P C -1
C1A C 0.605(3) 0.387(3) 0.9111(4) 0.082(6) Uani 0.1666 1 d . . P C -2
H1AA H 0.566024 0.351157 0.896010 0.123 Uiso 0.1666 1 calc R U P C -2
H1AB H 0.586141 0.438985 0.904771 0.123 Uiso 0.1666 1 calc R U P C -2
H1AC H 0.650156 0.380193 0.879457 0.123 Uiso 0.1666 1 calc R U P C -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 N1 2.037(3) . ?
Fe1 N1 2.037(3) 46_456 ?
Fe1 N1 2.037(3) 3_657 ?
Fe1 N1 2.037(3) 48_655 ?
N1 C2 1.372(4) . ?
N1 C3 1.385(5) . ?
C2 C1 1.435(10) . ?
C2 C1A 1.435(10) . ?
C3 C3 1.332(9) 14_665 ?
C3 H3 0.9300 . ?
C3 C5 1.699(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.434(14) . ?
C6 C6 1.355(19) 14_665 ?
C6 H6 0.9298 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C4 1.639(15) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?

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 111.84(9) . 46_456 ?
N1 Fe1 N1 111.85(9) . 48_655 ?
N1 Fe1 N1 111.85(9) 3_657 48_655 ?
N1 Fe1 N1 111.85(9) 46_456 3_657 ?
N1 Fe1 N1 104.82(17) . 3_657 ?
N1 Fe1 N1 104.82(17) 46_456 48_655 ?
C2 N1 Fe1 127.0(3) . . ?
C2 N1 C3 105.7(3) . . ?
C3 N1 Fe1 127.3(3) . . ?
N1 C2 N1 110.0(5) 14_665 . ?
N1 C2 C1 129(3) 14_665 . ?
N1 C2 C1 121(3) . . ?
N1 C2 C1A 121(3) . . ?
N1 C2 C1A 129(3) 14_665 . ?
N1 C3 H3 125.3 . . ?
N1 C3 C5 130.9(4) . . ?
C3 C3 N1 109.3(2) 14_665 . ?
C3 C3 H3 125.3 14_665 . ?
C3 C3 C5 119.4(3) 14_665 . ?
C3 C5 H5 122.1 . . ?
C6 C5 C3 115.7(8) . . ?
C6 C5 H5 122.1 . . ?
C5 C6 H6 114.2 . . ?
C6 C6 C5 124.9(6) 14_665 . ?
C6 C6 H6 120.9 14_665 . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C2 C1 C4 112.3(9) . . ?
H1A C1 H1B 107.9 . . ?
C4 C1 H1A 109.2 . . ?
C4 C1 H1B 109.2 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C1A H1AA 109.5 . . ?
C2 C1A H1AB 109.5 . . ?
C2 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 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 C2 N1 178.57(13) . . . 14_665 ?
Fe1 N1 C2 C1 2.3(8) . . . . ?
Fe1 N1 C2 C1A 2.3(8) . . . . ?
Fe1 N1 C3 C3 -178.48(17) . . . 14_665 ?
Fe1 N1 C3 C5 -6.2(7) . . . . ?
N1 C2 C1 C4 87(4) . . . . ?
N1 C2 C1 C4 -88(4) 14_665 . . . ?
N1 C3 C5 C6 -172.1(7) . . . . ?
C2 N1 C3 C3 -0.1(3) . . . 14_665 ?
C2 N1 C3 C5 172.1(6) . . . . ?
C3 N1 C2 N1 0.2(5) . . . 14_665 ?
C3 N1 C2 C1 -176.0(6) . . . . ?
C3 N1 C2 C1A -176.0(6) . . . . ?
C3 C3 C5 C6 -0.5(10) 14_665 . . . ?
C3 C5 C6 C6 0.6(10) . . . 14_665 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 844.8 176.8 '24 water'
2 0.500 0.500 0.500 844.8 176.8 '24 water'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.907
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.84(4)
2 0.16(4)

