# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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. 
# 
#######################################################################

data_mn_sq
_database_code_depnum_ccdc_archive 'CCDC 2220110'
loop_
_audit_author_name
_audit_author_address
'Lei Hou'
;Northwest University
China
;
_audit_update_record             
;
2022-11-16 deposited with the CCDC.	2022-12-28 downloaded from the CCDC.
;

_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 H8 Mn N5 O3'
_chemical_formula_weight         277.13

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           172
_space_group_name_H-M_alt        'P 64'
_space_group_name_Hall           'P 64'

_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+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z'
'y, -x+y, z+1/3'
'x-y, x, z+2/3'

_cell_length_a                   18.3490(3)
_cell_length_b                   18.3490(3)
_cell_length_c                   8.2189(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2396.45(10)
_cell_formula_units_Z            6
_cell_measurement_temperature    157(2)
_cell_measurement_reflns_used    13048
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   0.6601
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.829
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      157(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32741
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.790
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2939
_reflns_number_gt                2792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0363P)²+0.8654P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     157
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.303
_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
Mn1 Mn 0.71144(3) 0.42887(3) 0.08962(5) 0.01563(15) Uani 1 1 d . . . . .
N1 N 0.61447(19) 0.3868(2) -0.1037(4) 0.0179(7) Uani 1 1 d . . . . .
C1 C 0.5496(2) 0.3986(2) -0.1378(5) 0.0186(8) Uani 1 1 d . . . . .
C3 C 0.5000 0.5000 -0.1202(6) 0.0189(11) Uani 1 2 d S T P . .
H3 H 0.5000 0.5000 -0.2358 0.023 Uiso 1 2 calc R U P . .
C2 C 0.5226(2) 0.4483(2) -0.0369(4) 0.0180(8) Uani 1 1 d . . . . .
C4 C 0.5201(2) 0.4453(2) 0.1329(4) 0.0169(8) Uani 1 1 d . . . . .
O1 O 0.59799(17) 0.38287(17) 0.2434(3) 0.0229(6) Uani 1 1 d . . . . .
N2 N 0.62020(18) 0.34394(19) -0.2298(4) 0.0170(6) Uani 1 1 d . . . . .
O2 O 0.4697(2) 0.3374(2) 0.3255(5) 0.0436(9) Uani 1 1 d . . . . .
N4 N 0.5159(2) 0.3658(2) -0.2840(4) 0.0232(7) Uani 1 1 d . . . . .
C6 C 0.5293(2) 0.3839(2) 0.2384(4) 0.0189(8) Uani 1 1 d . . . . .
C5 C 0.5000 0.5000 0.2155(6) 0.0177(11) Uani 1 2 d S T P . .
H5 H 0.5000 0.5000 0.3311 0.021 Uiso 1 2 calc R U P . .
N3 N 0.5620(2) 0.3324(2) -0.3370(4) 0.0211(7) Uani 1 1 d . . . . .
O3 O 0.72217(17) 0.55041(18) 0.0893(4) 0.0353(7) Uani 1 1 d . U . . .
N5 N 0.7771(3) 0.6900(3) 0.1172(8) 0.0617(12) Uani 1 1 d . U . . .
C7 C 0.7806(3) 0.6201(3) 0.1227(8) 0.0485(11) Uani 1 1 d . U . . .
H7 H 0.8322 0.6242 0.1550 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7027(4) 0.6894(4) 0.0693(12) 0.0804(19) Uani 1 1 d . U . . .
H9A H 0.6731 0.6455 -0.0126 0.121 Uiso 1 1 calc R U . . .
H9B H 0.7172 0.7443 0.0230 0.121 Uiso 1 1 calc R U . . .
H9C H 0.6662 0.6781 0.1642 0.121 Uiso 1 1 calc R U . . .
C8 C 0.8445(5) 0.7708(5) 0.1444(13) 0.100(2) Uani 1 1 d . U . . .
H8A H 0.8914 0.7671 0.1924 0.150 Uiso 1 1 calc R U . . .
H8B H 0.8271 0.8009 0.2190 0.150 Uiso 1 1 calc R U . . .
H8C H 0.8624 0.8013 0.0409 0.150 Uiso 1 1 calc R U . . .


_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 O3 2.139(3) . ?
Mn1 O1 2.210(3) . ?
Mn1 O1 2.214(3) 3_664 ?
Mn1 N3 2.216(3) 3_665 ?
Mn1 N1 2.217(3) . ?
Mn1 N2 2.458(3) 2_655 ?
N1 N2 1.336(4) . ?
N1 C1 1.343(5) . ?
C1 N4 1.348(5) . ?
C1 C2 1.488(5) . ?
C3 C2 1.390(5) 4_665 ?
C3 C2 1.390(5) . ?
C3 H3 0.9500 . ?
C2 C4 1.397(5) . ?
C4 C5 1.405(4) . ?
C4 C6 1.496(5) . ?
O1 C6 1.272(4) . ?
O1 Mn1 2.214(3) 2_655 ?
N2 N3 1.318(4) . ?
N2 Mn1 2.458(3) 3_664 ?
O2 C6 1.225(5) . ?
N4 N3 1.340(4) . ?
C5 C4 1.405(4) 4_665 ?
C5 H5 0.9500 . ?
N3 Mn1 2.216(3) 2_654 ?
O3 C7 1.220(6) . ?
N5 C7 1.318(6) . ?
N5 C8 1.395(8) . ?
N5 C9 1.415(7) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
O3 Mn1 O1 88.68(11) . . ?
O3 Mn1 O1 118.85(11) . 3_664 ?
O1 Mn1 O1 149.09(9) . 3_664 ?
O3 Mn1 N3 97.77(13) . 3_665 ?
O1 Mn1 N3 81.43(11) . 3_665 ?
O1 Mn1 N3 106.37(12) 3_664 3_665 ?
O3 Mn1 N1 90.11(12) . . ?
O1 Mn1 N1 80.68(10) . . ?
O1 Mn1 N1 85.21(10) 3_664 . ?
N3 Mn1 N1 160.26(12) 3_665 . ?
O3 Mn1 N2 163.37(11) . 2_655 ?
O1 Mn1 N2 76.37(10) . 2_655 ?
O1 Mn1 N2 74.24(10) 3_664 2_655 ?
N3 Mn1 N2 87.30(11) 3_665 2_655 ?
N1 Mn1 N2 80.43(11) . 2_655 ?
N2 N1 C1 105.7(3) . . ?
N2 N1 Mn1 118.4(2) . . ?
C1 N1 Mn1 135.7(2) . . ?
N1 C1 N4 111.0(3) . . ?
N1 C1 C2 125.2(3) . . ?
N4 C1 C2 123.5(3) . . ?
C2 C3 C2 121.0(5) 4_665 . ?
C2 C3 H3 119.5 4_665 . ?
C2 C3 H3 119.5 . . ?
C3 C2 C4 120.3(4) . . ?
C3 C2 C1 116.6(3) . . ?
C4 C2 C1 123.1(3) . . ?
C2 C4 C5 118.0(4) . . ?
C2 C4 C6 126.5(3) . . ?
C5 C4 C6 115.2(3) . . ?
C6 O1 Mn1 136.7(2) . . ?
C6 O1 Mn1 102.9(2) . 2_655 ?
Mn1 O1 Mn1 118.31(11) . 2_655 ?
N3 N2 N1 108.5(3) . . ?
N3 N2 Mn1 126.9(2) . 3_664 ?
N1 N2 Mn1 124.5(2) . 3_664 ?
N3 N4 C1 103.9(3) . . ?
O2 C6 O1 121.1(3) . . ?
O2 C6 C4 117.8(3) . . ?
O1 C6 C4 121.0(3) . . ?
C4 C5 C4 122.2(5) 4_665 . ?
C4 C5 H5 118.9 4_665 . ?
C4 C5 H5 118.9 . . ?
N2 N3 N4 110.8(3) . . ?
N2 N3 Mn1 116.0(2) . 2_654 ?
N4 N3 Mn1 132.3(2) . 2_654 ?
C7 O3 Mn1 131.8(3) . . ?
C7 N5 C8 125.5(6) . . ?
C7 N5 C9 121.2(5) . . ?
C8 N5 C9 113.1(5) . . ?
O3 C7 N5 124.6(5) . . ?
O3 C7 H7 117.7 . . ?
N5 C7 H7 117.7 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.051



