# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20200531-hfp-wtx-20191231-20-ln-lin-mnbbbb_sq
_database_code_depnum_ccdc_archive 'CCDC 2381922'
loop_
_audit_author_name
_audit_author_address
'Han-Fu Liu'
;Guilin Medical University
China
;
_audit_update_record             
;
2024-09-04 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_audit_creation_date             2024-03-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Mn2 N8 O4'
_chemical_formula_sum            'C18 H14 Mn2 N8 O4'
_chemical_formula_weight         516.25
_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'
Mn Mn 0.3368 0.7283 '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'

_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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'
'-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'

_cell_length_a                   21.6779(8)
_cell_length_b                   21.6779(8)
_cell_length_c                   12.6682(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5155.6(4)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2540
_cell_measurement_theta_min      4.2200
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.726
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2340
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8753
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_min         3.255
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  94.00   1.00   45.00    --   17.77 178.00 -30.00   59
  2  ω    -41.00  49.00   1.00   45.00    --  -19.57  57.00 150.00   90
  3  ω     -8.00  88.00   1.00   45.00    --   17.77  38.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0154167000
_diffrn_orient_matrix_UB_12      -0.0372079000
_diffrn_orient_matrix_UB_13      -0.0080201000
_diffrn_orient_matrix_UB_21      -0.0316949000
_diffrn_orient_matrix_UB_22      -0.0057514000
_diffrn_orient_matrix_UB_23      0.0250933000
_diffrn_orient_matrix_UB_31      -0.0136232000
_diffrn_orient_matrix_UB_32      0.0031000000
_diffrn_orient_matrix_UB_33      -0.0494039000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1937
_reflns_number_total             2713
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    ?
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.064
_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)+(0.0474P)²+15.9024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O1, C1
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Mn1 Mn 0.41755(3) 0.25719(3) 0.34834(4) 0.02987(19) Uani 1 1 d . . . . .
O1 O 0.50681(18) 0.15594(16) 0.4408(2) 0.0582(8) Uani 1 1 d . U . . .
O2 O 0.49506(18) 0.25474(17) 0.4483(2) 0.0610(9) Uani 1 1 d . . . . .
N1 N 0.33837(14) 0.22866(13) 0.4913(2) 0.0289(6) Uani 1 1 d . . . . .
N2 N 0.44283(13) 0.35900(13) 0.4258(2) 0.0247(6) Uani 1 1 d . . . . .
N3 N 0.49000(14) 0.43027(13) 0.41123(19) 0.0254(6) Uani 1 1 d . . . . .
N4 N 0.42983(13) 0.41794(13) 0.5620(2) 0.0255(6) Uani 1 1 d . . . . .
C1 C 0.5276(3) 0.2211(3) 0.4526(5) 0.0760(15) Uani 1 1 d . U . . .
H1 H 0.575988 0.249120 0.467186 0.091 Uiso 1 1 calc R U . . .
C2 C 0.2680(2) 0.1028(2) 0.4503(3) 0.0574(12) Uani 1 1 d . . . . .
H2A H 0.252528 0.111134 0.383510 0.086 Uiso 1 1 calc R U . . .
H2B H 0.230460 0.059951 0.481102 0.086 Uiso 1 1 calc R U . . .
H2C H 0.309232 0.097958 0.440101 0.086 Uiso 1 1 calc R U . . .
C3 C 0.28610(18) 0.16363(18) 0.5217(3) 0.0349(8) Uani 1 1 d . . . . .
C4 C 0.25081(19) 0.15398(19) 0.6175(3) 0.0398(9) Uani 1 1 d . . . . .
H4 H 0.214895 0.108769 0.637060 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2687(2) 0.21053(19) 0.6829(3) 0.0418(9) Uani 1 1 d . . . . .
H5 H 0.245757 0.204291 0.747332 0.050 Uiso 1 1 calc R U . . .
C6 C 0.32168(19) 0.27743(19) 0.6510(3) 0.0348(8) Uani 1 1 d . . . . .
H6 H 0.334889 0.316981 0.693763 0.042 Uiso 1 1 calc R U . . .
C7 C 0.35446(16) 0.28448(16) 0.5553(2) 0.0245(6) Uani 1 1 d . . . . .
C8 C 0.40930(16) 0.35425(15) 0.5159(2) 0.0233(6) Uani 1 1 d . . . . .
C9 C 0.47970(16) 0.46159(16) 0.4933(2) 0.0261(7) Uani 1 1 d . . . . .


_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
Mn1 O1 2.112(3) 17 ?
Mn1 O2 2.125(3) . ?
Mn1 N1 2.355(3) . ?
Mn1 N2 2.219(2) . ?
Mn1 N3 2.293(2) 18_545 ?
Mn1 N4 2.432(3) 9_554 ?
O1 C1 1.259(6) . ?
O2 C1 1.244(6) . ?
N1 C3 1.350(4) . ?
N1 C7 1.350(4) . ?
N2 N3 1.374(3) . ?
N2 C8 1.329(4) . ?
N3 C9 1.320(4) . ?
N4 C8 1.353(4) . ?
N4 C9 1.341(4) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.480(5) . ?
C3 C4 1.394(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(4) . ?
C7 C8 1.467(4) . ?
C9 C9 1.453(6) 10_666 ?

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 Mn1 O2 95.68(12) 17 . ?
O1 Mn1 N1 160.60(11) 17 . ?
O1 Mn1 N2 89.14(11) 17 . ?
O1 Mn1 N3 86.88(11) 17 18_545 ?
O1 Mn1 N4 87.56(10) 17 9_554 ?
O2 Mn1 N1 90.98(11) . . ?
O2 Mn1 N2 87.49(10) . . ?
O2 Mn1 N3 95.29(10) . 18_545 ?
O2 Mn1 N4 169.41(10) . 9_554 ?
N1 Mn1 N4 89.20(9) . 9_554 ?
N2 Mn1 N1 72.92(9) . . ?
N2 Mn1 N3 175.35(9) . 18_545 ?
N2 Mn1 N4 102.67(9) . 9_554 ?
N3 Mn1 N1 110.67(9) 18_545 . ?
N3 Mn1 N4 74.77(9) 18_545 9_554 ?
C1 O1 Mn1 139.0(3) . 18_545 ?
C1 O2 Mn1 136.7(3) . . ?
C3 N1 Mn1 127.9(2) . . ?
C7 N1 Mn1 113.5(2) . . ?
C7 N1 C3 118.1(3) . . ?
N3 N2 Mn1 137.23(19) . . ?
C8 N2 Mn1 116.68(19) . . ?
C8 N2 N3 105.8(2) . . ?
N2 N3 Mn1 141.51(19) . 17 ?
C9 N3 Mn1 112.26(19) . 17 ?
C9 N3 N2 104.5(2) . . ?
C8 N4 Mn1 151.6(2) . 5 ?
C9 N4 Mn1 106.41(19) . 5 ?
C9 N4 C8 100.2(2) . . ?
O1 C1 H1 114.3 . . ?
O2 C1 O1 131.5(5) . . ?
O2 C1 H1 114.3 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
N1 C3 C2 117.8(3) . . ?
N1 C3 C4 121.1(3) . . ?
C4 C3 C2 121.1(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 120.5 . . ?
N1 C7 C6 122.9(3) . . ?
N1 C7 C8 115.6(3) . . ?
C6 C7 C8 121.5(3) . . ?
N2 C8 N4 113.8(3) . . ?
N2 C8 C7 120.1(3) . . ?
N4 C8 C7 126.0(3) . . ?
N3 C9 N4 115.6(3) . . ?
N3 C9 C9 121.4(3) . 10_666 ?
N4 C9 C9 123.0(3) . 10_666 ?

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
Mn1 O1 C1 O2 89.1(8) 18_545 . . . ?
Mn1 O2 C1 O1 -44.0(9) . . . . ?
Mn1 N1 C3 C2 -9.5(5) . . . . ?
Mn1 N1 C3 C4 169.9(3) . . . . ?
Mn1 N1 C7 C6 -170.3(3) . . . . ?
Mn1 N1 C7 C8 10.2(3) . . . . ?
Mn1 N2 N3 Mn1 -12.0(5) . . . 17 ?
Mn1 N2 N3 C9 -174.6(2) . . . . ?
Mn1 N2 C8 N4 176.6(2) . . . . ?
Mn1 N2 C8 C7 -4.7(4) . . . . ?
Mn1 N3 C9 N4 -168.4(2) 17 . . . ?
Mn1 N3 C9 C9 11.6(5) 17 . . 10_666 ?
Mn1 N4 C8 N2 158.6(3) 5 . . . ?
Mn1 N4 C8 C7 -19.9(6) 5 . . . ?
Mn1 N4 C9 N3 -169.4(2) 5 . . . ?
Mn1 N4 C9 C9 10.5(5) 5 . . 10_666 ?
N1 C3 C4 C5 -0.1(6) . . . . ?
N1 C7 C8 N2 -4.2(4) . . . . ?
N1 C7 C8 N4 174.3(3) . . . . ?
N2 N3 C9 N4 0.0(4) . . . . ?
N2 N3 C9 C9 -180.0(4) . . . 10_666 ?
N3 N2 C8 N4 1.3(3) . . . . ?
N3 N2 C8 C7 179.9(3) . . . . ?
C2 C3 C4 C5 179.3(4) . . . . ?
C3 N1 C7 C6 2.2(5) . . . . ?
C3 N1 C7 C8 -177.2(3) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 N1 -1.4(5) . . . . ?
C5 C6 C7 C8 178.0(3) . . . . ?
C6 C7 C8 N2 176.3(3) . . . . ?
C6 C7 C8 N4 -5.2(5) . . . . ?
C7 N1 C3 C2 179.1(3) . . . . ?
C7 N1 C3 C4 -1.5(5) . . . . ?
C8 N2 N3 Mn1 161.9(3) . . . 17 ?
C8 N2 N3 C9 -0.7(3) . . . . ?
C8 N4 C9 N3 0.7(4) . . . . ?
C8 N4 C9 C9 -179.3(4) . . . 10_666 ?
C9 N4 C8 N2 -1.2(3) . . . . ?
C9 N4 C8 C7 -179.8(3) . . . . ?

_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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.903
