# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_at61ewort_a
_database_code_depnum_ccdc_archive 'CCDC 1998328'
loop_
_audit_author_name
_audit_author_address
'Jerome Marrot'
;Institut Lavoisier de Versailles
France
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl Fe N5 O8'
_chemical_formula_weight         471.60

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-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'

_cell_length_a                   9.053(3)
_cell_length_b                   15.456(6)
_cell_length_c                   13.532(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1893.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    625
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      13.26

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   0.8174
_exptl_transmission_factor_max   0.8452
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.992
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2016/2)'
_exptl_absorpt_special_details   
'Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10'
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23471
_diffrn_reflns_av_unetI/netI     0.1728
_diffrn_reflns_av_R_equivalents  0.3827
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.607
_diffrn_reflns_theta_max         25.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1727
_reflns_number_gt                858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1929P)²+8.5800P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_number_reflns         1727
_refine_ls_number_parameters     126
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2185
_refine_ls_R_factor_gt           0.1233
_refine_ls_wR_factor_ref         0.3795
_refine_ls_wR_factor_gt          0.3242
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.067
_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 0.6756(4) 0.500000 0.500000 0.081(2) Uani 1 2 d S T P . .
N1 N 0.593(2) 0.3748(16) 0.4511(17) 0.084(7) Uani 1 1 d . . . . .
C2 C 0.651(3) 0.308(2) 0.419(2) 0.095(9) Uani 1 1 d . . . . .
H2 H 0.753729 0.299770 0.417393 0.114 Uiso 1 1 calc R U . . .
C3 C 0.545(3) 0.2399(17) 0.381(2) 0.085(9) Uani 1 1 d . . . . .
H3 H 0.563303 0.185388 0.353284 0.102 Uiso 1 1 calc R U . . .
C4 C 0.409(2) 0.2818(17) 0.4005(19) 0.072(7) Uani 1 1 d . . . . .
H4 H 0.313293 0.259763 0.389815 0.087 Uiso 1 1 calc R U . . .
N5 N 0.4467(19) 0.3631(14) 0.4387(16) 0.079(6) Uani 1 1 d . . . . .
C6 C 0.352(2) 0.4307(17) 0.4717(17) 0.072(7) Uani 1 1 d . . . . .
C7 C 0.202(2) 0.4317(15) 0.468(2) 0.085(10) Uani 1 1 d . . . . .
H7 H 0.151044 0.383541 0.442543 0.102 Uiso 1 1 calc R U . . .
C8 C 0.126(3) 0.500000 0.500000 0.090(8) Uani 1 2 d S T P . .
C9 C -0.051(3) 0.500000 0.500000 0.090(8) Uani 1 2 d S T P . .
N10 N 0.430(2) 0.500000 0.500000 0.068(7) Uani 1 2 d S T P . .
O11 O -0.1107(18) 0.4286(12) 0.4718(18) 0.106(8) Uani 1 1 d . . . . .
O12 O 0.674(3) 0.4555(12) 0.6465(15) 0.108(7) Uani 1 1 d . . . . .
C13 C 0.732(4) 0.494(2) 0.731(3) 0.149(13) Uiso 1 1 d . . . . .
H13A H 0.815594 0.530239 0.712372 0.223 Uiso 1 1 calc R U . . .
H13B H 0.765154 0.449607 0.776257 0.223 Uiso 1 1 calc R U . . .
H13C H 0.657219 0.529312 0.762120 0.223 Uiso 1 1 calc R U . . .
Cl1 Cl 0.500000 0.2641(6) 0.750000 0.082(3) Uani 1 2 d DS T P . .
O21 O 0.480(5) 0.286(2) 0.8521(18) 0.086(10) Uiso 0.5 1 d D . P . .
O22 O 0.427(6) 0.182(3) 0.761(5) 0.148(19) Uiso 0.5 1 d . . P . .
O20 O 0.413(5) 0.317(3) 0.681(3) 0.111(14) Uiso 0.5 1 d . . P . .
O23 O 0.355(8) 0.296(4) 0.777(4) 0.156(19) Uiso 0.5 1 d . . 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 O12 2.10(2) . ?
Fe1 O12 2.10(2) 4_566 ?
Fe1 N1 2.18(3) 4_566 ?
Fe1 N1 2.18(3) . ?
Fe1 O11 2.259(18) 4_666 ?
Fe1 O11 2.259(18) 1_655 ?
Fe1 N10 2.22(2) . ?
N1 C2 1.24(4) . ?
N1 N5 1.35(3) . ?
C2 C3 1.51(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.41(3) . ?
C3 H3 0.9400 . ?
C4 N5 1.40(3) . ?
C4 H4 0.9400 . ?
N5 C6 1.42(3) . ?
C6 N10 1.34(3) . ?
C6 C7 1.36(3) . ?
C7 C8 1.33(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.60(4) . ?
C9 O11 1.29(2) . ?
C9 O11 1.29(2) 4_566 ?
O12 C13 1.39(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
Cl1 O21 1.43(2) 3_656 ?
Cl1 O21 1.43(2) . ?
Cl1 O22 1.43(5) 3_656 ?
Cl1 O22 1.43(5) . ?
Cl1 O23 1.45(7) 3_656 ?
Cl1 O23 1.45(7) . ?
Cl1 O20 1.47(5) . ?
Cl1 O20 1.47(5) 3_656 ?
O21 O20 1.17(5) 3_656 ?
O21 O23 1.53(7) . ?
O22 O22 1.35(10) 3_656 ?
O20 O23 1.44(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
O12 Fe1 O12 179.2(14) . 4_566 ?
O12 Fe1 N1 90.1(8) . 4_566 ?
O12 Fe1 N1 89.6(8) 4_566 4_566 ?
O12 Fe1 N1 89.6(8) . . ?
O12 Fe1 N1 90.1(8) 4_566 . ?
N1 Fe1 N1 139.8(11) 4_566 . ?
O12 Fe1 O11 90.4(8) . 4_666 ?
O12 Fe1 O11 90.3(9) 4_566 4_666 ?
N1 Fe1 O11 79.0(7) 4_566 4_666 ?
N1 Fe1 O11 141.2(7) . 4_666 ?
O12 Fe1 O11 90.3(9) . 1_655 ?
O12 Fe1 O11 90.4(8) 4_566 1_655 ?
N1 Fe1 O11 141.2(7) 4_566 1_655 ?
N1 Fe1 O11 79.0(7) . 1_655 ?
O11 Fe1 O11 62.2(10) 4_666 1_655 ?
O12 Fe1 N10 89.6(7) . . ?
O12 Fe1 N10 89.6(7) 4_566 . ?
N1 Fe1 N10 69.9(5) 4_566 . ?
N1 Fe1 N10 69.9(5) . . ?
O11 Fe1 N10 148.9(5) 4_666 . ?
O11 Fe1 N10 148.9(5) 1_655 . ?
C2 N1 N5 105(2) . . ?
C2 N1 Fe1 134.7(17) . . ?
N5 N1 Fe1 119.7(18) . . ?
N1 C2 C3 115(2) . . ?
N1 C2 H2 122.3 . . ?
C3 C2 H2 122.3 . . ?
C4 C3 C2 100(2) . . ?
C4 C3 H3 130.0 . . ?
C2 C3 H3 130.0 . . ?
N5 C4 C3 105(2) . . ?
N5 C4 H4 127.3 . . ?
C3 C4 H4 127.3 . . ?
N1 N5 C4 114(2) . . ?
N1 N5 C6 117(2) . . ?
C4 N5 C6 128.8(18) . . ?
N10 C6 C7 122(2) . . ?
N10 C6 N5 111.0(17) . . ?
C7 C6 N5 127(2) . . ?
C8 C7 C6 121(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C7 118(3) . 4_566 ?
C7 C8 C9 121.1(15) . . ?
C7 C8 C9 121.1(15) 4_566 . ?
O11 C9 O11 130(3) . 4_566 ?
O11 C9 C8 115.0(15) . . ?
O11 C9 C8 115.0(15) 4_566 . ?
C6 N10 C6 116(3) 4_566 . ?
C6 N10 Fe1 121.9(13) 4_566 . ?
C6 N10 Fe1 121.9(13) . . ?
C9 O11 Fe1 83.9(16) . 1_455 ?
C13 O12 Fe1 129(2) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O21 Cl1 O21 153(3) 3_656 . ?
O21 Cl1 O22 93(3) 3_656 3_656 ?
O21 Cl1 O22 111(3) . 3_656 ?
O21 Cl1 O22 111(3) 3_656 . ?
O21 Cl1 O22 93(3) . . ?
O22 Cl1 O22 56(4) 3_656 . ?
O21 Cl1 O23 64(3) 3_656 3_656 ?
O21 Cl1 O23 106(3) . 3_656 ?
O22 Cl1 O23 82(3) 3_656 3_656 ?
O22 Cl1 O23 138(3) . 3_656 ?
O21 Cl1 O23 106(3) 3_656 . ?
O21 Cl1 O23 64(3) . . ?
O22 Cl1 O23 138(3) 3_656 . ?
O22 Cl1 O23 82(3) . . ?
O23 Cl1 O23 140(4) 3_656 . ?
O21 Cl1 O20 48(2) 3_656 . ?
O21 Cl1 O20 115(2) . . ?
O22 Cl1 O20 132(3) 3_656 . ?
O22 Cl1 O20 108(3) . . ?
O23 Cl1 O20 98(3) 3_656 . ?
O23 Cl1 O20 59(3) . . ?
O21 Cl1 O20 115(2) 3_656 3_656 ?
O21 Cl1 O20 48(2) . 3_656 ?
O22 Cl1 O20 108(3) 3_656 3_656 ?
O22 Cl1 O20 132(3) . 3_656 ?
O23 Cl1 O20 59(3) 3_656 3_656 ?
O23 Cl1 O20 98(3) . 3_656 ?
O20 Cl1 O20 112(3) . 3_656 ?
O20 O21 Cl1 68(3) 3_656 . ?
O20 O21 O23 109(4) 3_656 . ?
Cl1 O21 O23 59(3) . . ?
O22 O22 Cl1 62(2) 3_656 . ?
O21 O20 O23 124(5) 3_656 . ?
O21 O20 Cl1 64(3) 3_656 . ?
O23 O20 Cl1 60(3) . . ?
O20 O23 Cl1 61(3) . . ?
O20 O23 O21 111(5) . . ?
Cl1 O23 O21 57(3) . . ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.145

