# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_SUM-31
_database_code_depnum_ccdc_archive 'CCDC 2223527'
loop_
_audit_author_name
_audit_author_address
'Chong Liu'
;Sichuan University
China
;
_audit_update_record             
;
2022-12-01 deposited with the CCDC.	2023-02-10 downloaded from the CCDC.
;
_audit_creation_date             2021-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Fe2 N6 O12'
_chemical_formula_sum            'C12 H12 Fe2 N6 O12'
_chemical_formula_weight         543.98
_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 0.0137 0.0067 '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 -0.2673 2.5550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   13.635(18)
_cell_length_b                   21.87(2)
_cell_length_c                   17.252(18)
_cell_angle_alpha                90
_cell_angle_beta                 111.89(5)
_cell_angle_gamma                90
_cell_volume                     4773(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    711
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      46.38
_cell_measurement_theta_min      8.73
_shelx_estimated_absorpt_T_max   0.717
_shelx_estimated_absorpt_T_min   0.674
_exptl_absorpt_coefficient_mu    3.568
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.4287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1384 before and 0.0928 after correction.
The Ratio of minimum to maximum transmission is 0.5702.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    0.757
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15851
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.797
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2130
_reflns_number_total             5217
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5217
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0922
_refine_ls_restrained_S_all      0.956
_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)+(0.1817P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2820
_refine_ls_wR_factor_ref         0.3227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C6B-C6B_$1 \\sim C6A-C6A_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O2B \\sim O1B \\sim N3B \\sim C5B \\sim C6B \\sim C6A \\sim C5A \\sim O1A \\sim
N3A \\sim O2A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
4. Others
 Sof(O2B)=Sof(O1B)=Sof(N3B)=Sof(H3B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=1-FVAR(1)
 Sof(C6A)=Sof(H6A)=Sof(C5A)=Sof(O1A)=Sof(N3A)=Sof(H3A)=Sof(O2A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3B(H3B), N1(H1), C3(H3), C2(H2A), C6B(H6B), C6A(H6A), N3A(H3A)
;
_atom_sites_solution_hydrogens   geom
_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 0.80721(8) 0.54775(5) 0.03562(5) 0.0793(4) Uani 1 1 d . . . . .
O4 O 0.8311(3) 0.54237(18) 0.1566(2) 0.0739(11) Uani 1 1 d . . . . .
O6 O 0.8947(3) 0.52380(18) 0.5423(2) 0.0714(11) Uani 1 1 d . . . . .
O5 O 0.7650(4) 0.4707(2) 0.4137(2) 0.0924(15) Uani 1 1 d . . . . .
O2B O 0.9341(18) 0.5911(8) 0.0423(11) 0.064(3) Uani 0.540(19) 1 d . U P A 2
N2 N 0.8952(4) 0.5382(2) 0.4665(3) 0.0686(13) Uani 1 1 d . . . . .
H2 H 0.939156 0.565662 0.460765 0.082 Uiso 1 1 calc R U . . .
O1B O 0.7346(12) 0.6246(6) 0.0045(9) 0.072(3) Uani 0.540(19) 1 d . U P A 2
O3 O 0.6697(4) 0.5142(3) 0.0290(2) 0.1103(17) Uani 1 1 d . . . . .
N3B N 0.9018(15) 0.6556(7) 0.0252(9) 0.072(3) Uani 0.540(19) 1 d . U P A 2
H3B H 0.948283 0.682177 0.021446 0.086 Uiso 0.540(19) 1 calc R U P A 2
N1 N 0.6727(5) 0.5029(4) 0.1072(3) 0.117(2) Uani 1 1 d . . . . .
H1 H 0.618392 0.485820 0.114642 0.140 Uiso 1 1 calc R U . . .
C4 C 0.8287(5) 0.5102(3) 0.4025(3) 0.0741(17) Uani 1 1 d . . . . .
C5B C 0.8165(16) 0.6731(9) 0.0162(10) 0.071(3) Uani 0.540(19) 1 d . U P A 2
C3 C 0.8315(5) 0.5253(3) 0.3209(3) 0.0675(15) Uani 1 1 d . . . . .
H3 H 0.887662 0.549062 0.316822 0.081 Uiso 1 1 calc R U . . .
C1 C 0.7549(6) 0.5173(3) 0.1692(3) 0.0808(18) Uani 1 1 d . . . . .
C2 C 0.7530(6) 0.5049(4) 0.2513(4) 0.091(2) Uani 1 1 d . . . . .
H2A H 0.696130 0.482244 0.256165 0.109 Uiso 1 1 calc R U . . .
C6B C 0.7872(11) 0.7295(7) 0.0002(10) 0.071(3) Uani 0.540(19) 1 d D U P A 2
H6B H 0.836455 0.749586 -0.018089 0.085 Uiso 0.540(19) 1 calc R U P A 2
C6A C 0.8041(8) 0.7473(9) 0.0195(11) 0.073(3) Uani 0.460(19) 1 d D U P A 1
H6A H 0.848733 0.782286 0.033198 0.087 Uiso 0.460(19) 1 calc R U P A 1
C5A C 0.8471(19) 0.6856(9) 0.0388(13) 0.074(3) Uani 0.460(19) 1 d . U P A 1
O1A O 0.7710(14) 0.6452(8) 0.0203(9) 0.072(3) Uani 0.460(19) 1 d . U P A 1
N3A N 0.9315(15) 0.6624(8) 0.0535(10) 0.069(3) Uani 0.460(19) 1 d . U P A 1
H3A H 0.985643 0.686414 0.059276 0.083 Uiso 0.460(19) 1 calc R U P A 1
O2A O 0.948(2) 0.6038(11) 0.0614(12) 0.067(3) Uani 0.460(19) 1 d . U P A 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 O4 1.992(4) . ?
Fe1 O6 1.945(4) 6_565 ?
Fe1 O5 2.004(4) 6_565 ?
Fe1 O2B 1.94(2) . ?
Fe1 O1B 1.924(11) . ?
Fe1 O3 1.976(6) . ?
Fe1 O1A 2.182(16) . ?
Fe1 O2A 2.18(3) . ?
O4 C1 1.264(7) . ?
O6 N2 1.348(5) . ?
O5 C4 1.288(7) . ?
O2B N3B 1.47(2) . ?
N2 H2 0.8800 . ?
N2 C4 1.292(7) . ?
O1B C5B 1.498(18) . ?
O3 N1 1.357(6) . ?
N3B H3B 0.8800 . ?
N3B C5B 1.18(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.268(8) . ?
C4 C3 1.460(7) . ?
C5B C6B 1.29(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.352(8) . ?
C1 C2 1.451(7) . ?
C2 H2A 0.9500 . ?
C6B C6B 1.353(16) 7_665 ?
C6B H6B 0.9500 . ?
C6A C6A 1.381(18) 7_665 ?
C6A H6A 0.9500 . ?
C6A C5A 1.46(2) . ?
C5A O1A 1.31(2) . ?
C5A N3A 1.19(2) . ?
N3A H3A 0.8800 . ?
N3A O2A 1.30(2) . ?

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 O5 163.4(2) . 6_565 ?
O4 Fe1 O1A 97.2(4) . . ?
O4 Fe1 O2A 91.8(6) . . ?
O6 Fe1 O4 91.89(15) 6_565 . ?
O6 Fe1 O5 80.20(16) 6_565 6_565 ?
O6 Fe1 O3 104.6(2) 6_565 . ?
O6 Fe1 O1A 154.1(5) 6_565 . ?
O6 Fe1 O2A 88.1(7) 6_565 . ?
O5 Fe1 O1A 96.1(4) 6_565 . ?
O5 Fe1 O2A 102.4(5) 6_565 . ?
O2B Fe1 O4 100.0(5) . . ?
O2B Fe1 O5 93.5(5) . 6_565 ?
O2B Fe1 O3 172.5(6) . . ?
O1B Fe1 O4 102.1(4) . . ?
O1B Fe1 O5 88.1(4) . 6_565 ?
O1B Fe1 O2B 86.8(7) . . ?
O1B Fe1 O3 86.0(5) . . ?
O3 Fe1 O4 79.61(18) . . ?
O3 Fe1 O5 88.2(2) . 6_565 ?
O3 Fe1 O1A 100.9(6) . . ?
O3 Fe1 O2A 164.8(6) . . ?
O2A Fe1 O1A 67.5(9) . . ?
C1 O4 Fe1 112.5(4) . . ?
N2 O6 Fe1 110.8(3) . 6_566 ?
C4 O5 Fe1 110.3(3) . 6_566 ?
N3B O2B Fe1 105.2(12) . . ?
O6 N2 H2 121.2 . . ?
C4 N2 O6 117.6(5) . . ?
C4 N2 H2 121.2 . . ?
C5B O1B Fe1 107.5(9) . . ?
N1 O3 Fe1 109.5(4) . . ?
O2B N3B H3B 118.5 . . ?
C5B N3B O2B 123.0(15) . . ?
C5B N3B H3B 118.5 . . ?
O3 N1 H1 120.6 . . ?
C1 N1 O3 118.9(6) . . ?
C1 N1 H1 120.6 . . ?
O5 C4 N2 119.1(5) . . ?
O5 C4 C3 123.8(5) . . ?
N2 C4 C3 117.0(6) . . ?
N3B C5B O1B 115.9(15) . . ?
N3B C5B C6B 123.3(17) . . ?
C6B C5B O1B 119.4(14) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.0(6) . . ?
C2 C3 H3 120.5 . . ?
O4 C1 N1 119.2(5) . . ?
O4 C1 C2 124.3(6) . . ?
N1 C1 C2 116.5(6) . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C5B C6B H6B 108.2 . . ?
C6B C6B H6B 108.2 7_665 . ?
C6A C6A H6A 121.5 7_665 . ?
C6A C6A C5A 117(2) 7_665 . ?
C5A C6A H6A 121.5 . . ?
O1A C5A C6A 110.7(16) . . ?
N3A C5A C6A 135.4(18) . . ?
N3A C5A O1A 112.4(15) . . ?
C5A O1A Fe1 120.4(11) . . ?
C5A N3A H3A 118.2 . . ?
C5A N3A O2A 123.6(17) . . ?
O2A N3A H3A 118.2 . . ?
N3A O2A Fe1 115.6(16) . . ?

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 O4 C1 N1 -4.7(9) . . . . ?
Fe1 O4 C1 C2 177.1(6) . . . . ?
Fe1 O6 N2 C4 10.1(6) 6_566 . . . ?
Fe1 O5 C4 N2 -10.7(7) 6_566 . . . ?
Fe1 O5 C4 C3 168.7(5) 6_566 . . . ?
Fe1 O2B N3B C5B 4.9(15) . . . . ?
Fe1 O1B C5B N3B 14.0(15) . . . . ?
Fe1 O1B C5B C6B -179.2(11) . . . . ?
Fe1 O3 N1 C1 3.5(9) . . . . ?
O4 C1 C2 C3 6.2(11) . . . . ?
O6 N2 C4 O5 0.7(9) . . . . ?
O6 N2 C4 C3 -178.8(5) . . . . ?
O5 C4 C3 C2 11.2(10) . . . . ?
O2B N3B C5B O1B -12.9(18) . . . . ?
O2B N3B C5B C6B -179.2(11) . . . . ?
N2 C4 C3 C2 -169.4(6) . . . . ?
O1B C5B C6B C6B 30(4) . . . 7_665 ?
O3 N1 C1 O4 0.8(11) . . . . ?
O3 N1 C1 C2 179.2(6) . . . . ?
N3B C5B C6B C6B -164(3) . . . 7_665 ?
N1 C1 C2 C3 -172.0(7) . . . . ?
C4 C3 C2 C1 -178.0(6) . . . . ?
C6A C6A C5A O1A -5(2) 7_665 . . . ?
C6A C6A C5A N3A 160(3) 7_665 . . . ?
C6A C5A O1A Fe1 177.0(10) . . . . ?
C6A C5A N3A O2A -173.2(16) . . . . ?
C5A N3A O2A Fe1 5(2) . . . . ?
O1A C5A N3A O2A -9(2) . . . . ?
N3A C5A O1A Fe1 8.7(19) . . . . ?

_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 -0.849 -0.178 -0.929 3263.1 796.5 '20 DMF'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
