# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_2_sq
_database_code_depnum_ccdc_archive 'CCDC 2231939'
loop_
_audit_author_name
_audit_author_address
'Xiu-Mei Zhang'
;Huaibei Normal University
China
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 Mn2 N2 O11'
_chemical_formula_weight         644.30

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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   24.7409(12)
_cell_length_b                   15.0833(12)
_cell_length_c                   8.7224(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.585(3)
_cell_angle_gamma                90
_cell_volume                     3102.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2774
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.870
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7223
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72298
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2999
_reflns_number_gt                2725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0506P)²+4.2591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_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 0.22659(2) 0.000000 0.25081(4) 0.02646(13) Uani 1 2 d S T P . .
Mn2 Mn 0.29476(2) 0.000000 0.83183(5) 0.03008(13) Uani 1 2 d S T P . .
O1 O 0.20225(6) 0.10214(10) 0.39202(16) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.27147(6) 0.10075(10) 0.62602(17) 0.0368(3) Uani 1 1 d . . . . .
O3 O 0.24935(7) 0.39845(10) 0.89073(18) 0.0433(4) Uani 1 1 d . . . . .
O4 O 0.17696(7) 0.39571(11) 0.99283(18) 0.0454(4) Uani 1 1 d . . . . .
O5 O 0.31581(9) 0.000000 0.4199(3) 0.0537(6) Uani 1 2 d S T P . .
H5 H 0.316800 -0.044870 0.479694 0.064 Uiso 1 1 d R U . . .
O6 O 0.38015(10) 0.000000 0.8071(3) 0.0603(7) Uani 1 2 d S T P . .
H6A H 0.401115 -0.035360 0.875534 0.090 Uiso 0.5 1 d R U P . .
H6B H 0.378615 -0.016660 0.712804 0.090 Uiso 0.5 1 d R U P . .
O7 O 0.20881(8) 0.000000 0.8239(2) 0.0374(5) Uani 1 2 d S T P . .
H7 H 0.206087 0.044830 0.880211 0.045 Uiso 1 1 d R U . . .
N1 N -0.13829(9) 0.000000 -0.0801(3) 0.0297(5) Uani 1 2 d S T P . .
N2 N 0.12341(9) 0.000000 0.5448(3) 0.0266(5) Uani 1 2 d S T P . .
C1 C 0.22224(8) 0.12081(12) 0.5384(2) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.18459(8) 0.17389(13) 0.6114(2) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.20827(8) 0.24278(13) 0.7157(2) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.247006 0.253538 0.741701 0.036 Uiso 1 1 calc R U . . .
C4 C 0.17533(8) 0.29588(13) 0.7819(2) 0.0301(4) Uani 1 1 d . . . . .
C5 C 0.11732(9) 0.28070(15) 0.7402(3) 0.0385(5) Uani 1 1 d . . . . .
H5A H 0.094704 0.315837 0.783580 0.046 Uiso 1 1 calc R U . . .
C6 C 0.09325(8) 0.21325(15) 0.6342(2) 0.0367(5) Uani 1 1 d . . . . .
H6 H 0.054218 0.204765 0.604526 0.044 Uiso 1 1 calc R U . . .
C7 C 0.12596(8) 0.15796(13) 0.5709(2) 0.0285(4) Uani 1 1 d . . . . .
C8 C 0.20245(9) 0.36933(13) 0.8966(2) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.09927(7) 0.07662(13) 0.4821(2) 0.0270(4) Uani 1 1 d . . . . .
C10 C 0.04957(7) 0.07917(13) 0.3531(2) 0.0291(4) Uani 1 1 d . . . . .
H10 H 0.033765 0.133295 0.311548 0.035 Uiso 1 1 calc R U . . .
C11 C 0.02367(11) 0.000000 0.2866(3) 0.0263(5) Uani 1 2 d S T P . .
C12 C -0.03121(11) 0.000000 0.1539(3) 0.0267(5) Uani 1 2 d S T P . .
C13 C -0.05844(9) -0.07757(14) 0.0899(3) 0.0420(5) Uani 1 1 d . . . . .
H13 H -0.041219 -0.131911 0.123973 0.050 Uiso 1 1 calc R U . . .
C14 C -0.11132(9) -0.07490(15) -0.0248(3) 0.0433(5) Uani 1 1 d . . . . .
H14 H -0.128732 -0.128266 -0.064902 0.052 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 2.1607(15) 4_546 ?
Mn1 O3 2.1607(15) 7_556 ?
Mn1 O1 2.1682(14) 6 ?
Mn1 O1 2.1683(14) . ?
Mn1 N1 2.241(2) 5 ?
Mn1 O5 2.254(2) . ?
Mn2 O7 2.107(2) . ?
Mn2 O4 2.1579(15) 7_557 ?
Mn2 O4 2.1579(15) 4_547 ?
Mn2 O6 2.188(2) . ?
Mn2 O2 2.2888(15) 6 ?
Mn2 O2 2.2888(15) . ?
O1 C1 1.254(2) . ?
O2 C1 1.264(2) . ?
O3 C8 1.256(2) . ?
O4 C8 1.257(2) . ?
O5 H5 0.8500 . ?
O5 H5 0.8500 6 ?
O6 H6A 0.8500 . ?
O6 H6B 0.8500 . ?
O6 H6A 0.8500 6 ?
O6 H6B 0.8500 6 ?
O7 H7 0.8501 . ?
O7 H7 0.8501 6 ?
N1 C14 1.327(2) 6 ?
N1 C14 1.327(2) . ?
N2 C9 1.339(2) 6 ?
N2 C9 1.340(2) . ?
C1 C2 1.508(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.406(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 C8 1.508(3) . ?
C5 C6 1.383(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C9 1.494(3) . ?
C9 C10 1.394(2) . ?
C10 C11 1.396(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.494(3) . ?
C12 C13 1.381(3) 6 ?
C12 C13 1.381(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 H14 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
O3 Mn1 O3 90.29(8) 4_546 7_556 ?
O3 Mn1 O1 89.58(6) 4_546 6 ?
O3 Mn1 O1 179.78(6) 7_556 6 ?
O3 Mn1 O1 179.78(6) 4_546 . ?
O3 Mn1 O1 89.58(6) 7_556 . ?
O1 Mn1 O1 90.55(8) 6 . ?
O3 Mn1 N1 90.12(6) 4_546 5 ?
O3 Mn1 N1 90.12(6) 7_556 5 ?
O1 Mn1 N1 89.71(6) 6 5 ?
O1 Mn1 N1 89.71(6) . 5 ?
O3 Mn1 O5 89.40(6) 4_546 . ?
O3 Mn1 O5 89.40(6) 7_556 . ?
O1 Mn1 O5 90.77(6) 6 . ?
O1 Mn1 O5 90.77(6) . . ?
N1 Mn1 O5 179.32(8) 5 . ?
O7 Mn2 O4 97.54(6) . 7_557 ?
O7 Mn2 O4 97.54(6) . 4_547 ?
O4 Mn2 O4 93.60(10) 7_557 4_547 ?
O7 Mn2 O6 172.83(9) . . ?
O4 Mn2 O6 87.35(6) 7_557 . ?
O4 Mn2 O6 87.35(6) 4_547 . ?
O7 Mn2 O2 87.82(5) . 6 ?
O4 Mn2 O2 172.20(6) 7_557 6 ?
O4 Mn2 O2 91.31(6) 4_547 6 ?
O6 Mn2 O2 86.82(6) . 6 ?
O7 Mn2 O2 87.82(5) . . ?
O4 Mn2 O2 91.31(6) 7_557 . ?
O4 Mn2 O2 172.20(6) 4_547 . ?
O6 Mn2 O2 86.82(6) . . ?
O2 Mn2 O2 83.20(7) 6 . ?
C1 O1 Mn1 130.25(13) . . ?
C1 O2 Mn2 126.99(13) . . ?
C8 O3 Mn1 133.52(15) . 7_556 ?
C8 O4 Mn2 125.67(14) . 7_557 ?
Mn1 O5 H5 104.0 . . ?
Mn1 O5 H5 104.03(3) . 6 ?
H5 O5 H5 105.5 . 6 ?
Mn2 O6 H6A 109.5 . . ?
Mn2 O6 H6B 109.5 . . ?
H6A O6 H6B 109.5 . . ?
Mn2 O6 H6A 109.48(5) . 6 ?
H6A O6 H6A 77.7 . 6 ?
H6B O6 H6A 134.8 . 6 ?
Mn2 O6 H6B 109.46(7) . 6 ?
H6A O6 H6B 134.8 . 6 ?
H6B O6 H6B 34.4 . 6 ?
H6A O6 H6B 109.5 6 6 ?
Mn2 O7 H7 103.7 . . ?
Mn2 O7 H7 103.67(3) . 6 ?
H7 O7 H7 105.4 . 6 ?
C14 N1 C14 116.8(2) 6 . ?
C14 N1 Mn1 121.60(12) 6 5 ?
C14 N1 Mn1 121.60(12) . 5 ?
C9 N2 C9 119.2(2) 6 . ?
O1 C1 O2 125.01(18) . . ?
O1 C1 C2 116.46(17) . . ?
O2 C1 C2 118.50(16) . . ?
C3 C2 C7 119.43(17) . . ?
C3 C2 C1 118.82(16) . . ?
C7 C2 C1 121.69(17) . . ?
C4 C3 C2 121.35(17) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.11(18) . . ?
C3 C4 C8 120.06(17) . . ?
C5 C4 C8 120.83(18) . . ?
C6 C5 C4 119.90(19) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C7 121.54(18) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 118.61(17) . . ?
C6 C7 C9 118.71(17) . . ?
C2 C7 C9 122.09(17) . . ?
O3 C8 O4 124.93(18) . . ?
O3 C8 C4 117.47(17) . . ?
O4 C8 C4 117.59(18) . . ?
N2 C9 C10 121.96(17) . . ?
N2 C9 C7 115.08(15) . . ?
C10 C9 C7 122.66(17) . . ?
C9 C10 C11 119.60(18) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C10 117.6(2) . 6 ?
C10 C11 C12 121.16(11) . . ?
C10 C11 C12 121.16(11) 6 . ?
C13 C12 C13 115.8(2) 6 . ?
C13 C12 C11 122.07(12) 6 . ?
C13 C12 C11 122.08(12) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
N1 C14 C13 123.3(2) . . ?
N1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?

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 22.0(3) . . . . ?
Mn1 O1 C1 C2 -160.12(12) . . . . ?
Mn2 O2 C1 O1 -110.83(19) . . . . ?
Mn2 O2 C1 C2 71.3(2) . . . . ?
O1 C1 C2 C3 -137.56(19) . . . . ?
O2 C1 C2 C3 40.5(3) . . . . ?
O1 C1 C2 C7 39.5(3) . . . . ?
O2 C1 C2 C7 -142.48(19) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C4 177.65(17) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C8 179.13(17) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C8 C4 C5 C6 179.67(19) . . . . ?
C4 C5 C6 C7 1.9(3) . . . . ?
C5 C6 C7 C2 -2.7(3) . . . . ?
C5 C6 C7 C9 168.76(19) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C1 C2 C7 C6 -175.62(18) . . . . ?
C3 C2 C7 C9 -169.68(17) . . . . ?
C1 C2 C7 C9 13.3(3) . . . . ?
Mn1 O3 C8 O4 -94.2(2) 7_556 . . . ?
Mn1 O3 C8 C4 87.2(2) 7_556 . . . ?
Mn2 O4 C8 O3 1.9(3) 7_557 . . . ?
Mn2 O4 C8 C4 -179.46(13) 7_557 . . . ?
C3 C4 C8 O3 21.9(3) . . . . ?
C5 C4 C8 O3 -157.7(2) . . . . ?
C3 C4 C8 O4 -156.85(19) . . . . ?
C5 C4 C8 O4 23.6(3) . . . . ?
C9 N2 C9 C10 0.1(3) 6 . . . ?
C9 N2 C9 C7 173.95(14) 6 . . . ?
C6 C7 C9 N2 -119.8(2) . . . . ?
C2 C7 C9 N2 51.3(3) . . . . ?
C6 C7 C9 C10 54.1(3) . . . . ?
C2 C7 C9 C10 -134.81(19) . . . . ?
N2 C9 C10 C11 0.2(3) . . . . ?
C7 C9 C10 C11 -173.21(19) . . . . ?
C9 C10 C11 C10 -0.5(4) . . . 6 ?
C9 C10 C11 C12 176.8(2) . . . . ?
C10 C11 C12 C13 0.7(4) . . . 6 ?
C10 C11 C12 C13 177.9(2) 6 . . 6 ?
C10 C11 C12 C13 -177.9(2) . . . . ?
C10 C11 C12 C13 -0.7(4) 6 . . . ?
C13 C12 C13 C14 -3.5(4) 6 . . . ?
C11 C12 C13 C14 175.2(2) . . . . ?
C14 N1 C14 C13 2.4(5) 6 . . . ?
Mn1 N1 C14 C13 -175.03(19) 5 . . . ?
C12 C13 C14 N1 0.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.85 2.11 2.817(2) 140.0 6 yes
O6 H6B O5 0.85 2.57 3.270(3) 140.4 . yes
O7 H7 O3 0.85 2.15 2.838(2) 138.3 7_557 yes

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.047



