# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2308991'
loop_
_audit_author_name
_audit_author_address
'Shimin Zhang'
;Shanxi Normal University
China
;
_audit_update_record             
;
2023-11-20 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_audit_creation_date             2023-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Mn N2 O10'
_chemical_formula_sum            'C18 H12 Mn N2 O10'
_chemical_formula_weight         471.24
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.694(3)
_cell_length_b                   13.298(9)
_cell_length_c                   13.810(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.671(16)
_cell_angle_gamma                90
_cell_volume                     859.2(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.432
_cell_measurement_theta_min      2.960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             478
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12356
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_min         2.129
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1403
_reflns_number_total             2144
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.052
_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)+(0.0579P)²+0.2889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O5(H5a,H5b)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
Mn1 Mn 0.500000 1.000000 0.500000 0.0266(2) Uani 1 2 d S . P . .
O1 O -0.1104(5) 0.70973(16) 0.57420(18) 0.0445(6) Uani 1 1 d . . . . .
O2 O 0.1576(5) 0.67517(18) 0.26735(18) 0.0544(7) Uani 1 1 d . . . . .
O3 O -0.1753(4) 0.95374(15) 0.40048(14) 0.0307(5) Uani 1 1 d . . . . .
O4 O 0.2365(4) 0.87655(14) 0.44520(16) 0.0353(5) Uani 1 1 d . . . . .
O5 O 0.7216(5) 0.90707(16) 0.61167(15) 0.0434(6) Uani 1 1 d . . . . .
H5A H 0.708813 0.845505 0.594651 0.065 Uiso 1 1 d R U . . .
H5B H 0.900323 0.919565 0.614661 0.065 Uiso 1 1 d R U . . .
N1 N 0.0175(5) 0.69064(16) 0.42025(19) 0.0310(6) Uani 1 1 d . . . . .
C1 C 0.7036(6) 0.4319(2) 0.3505(2) 0.0342(7) Uani 1 1 d . . . . .
H1 H 0.801165 0.396229 0.305679 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5115(7) 0.5079(2) 0.3187(2) 0.0360(7) Uani 1 1 d . . . . .
H2 H 0.481648 0.522256 0.252752 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3667(6) 0.5614(2) 0.3844(2) 0.0257(6) Uani 1 1 d . . . . .
C4 C 0.4026(6) 0.5380(2) 0.4840(2) 0.0232(6) Uani 1 1 d . . . . .
C5 C 0.2520(6) 0.5899(2) 0.5527(2) 0.0267(6) Uani 1 1 d . . . . .
C6 C 0.0397(6) 0.6676(2) 0.5185(2) 0.0318(7) Uani 1 1 d . . . . .
C7 C 0.1770(6) 0.6453(2) 0.3503(2) 0.0333(7) Uani 1 1 d . . . . .
C8 C -0.1645(6) 0.7767(2) 0.3893(3) 0.0370(8) Uani 1 1 d . . . . .
H8A H -0.341670 0.772868 0.420659 0.044 Uiso 1 1 calc R U . . .
H8B H -0.211436 0.772917 0.319633 0.044 Uiso 1 1 calc R U . . .
C9 C -0.0204(6) 0.8769(2) 0.4139(2) 0.0272(6) 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 O3 2.221(2) 3_576 ?
Mn1 O3 2.221(2) 1_655 ?
Mn1 O4 2.155(2) 3_676 ?
Mn1 O4 2.155(2) . ?
Mn1 O5 2.174(2) . ?
Mn1 O5 2.174(2) 3_676 ?
O1 C6 1.221(4) . ?
O2 C7 1.209(4) . ?
O3 C9 1.259(3) . ?
O4 C9 1.248(3) . ?
O5 H5A 0.8526 . ?
O5 H5B 0.8528 . ?
N1 C6 1.387(4) . ?
N1 C7 1.405(4) . ?
N1 C8 1.471(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.401(4) . ?
C1 C5 1.367(4) 3_666 ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C3 C4 1.406(4) . ?
C3 C7 1.480(4) . ?
C4 C4 1.410(6) 3_666 ?
C4 C5 1.409(4) . ?
C5 C6 1.485(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.520(4) . ?

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 180.0 1_655 3_576 ?
O4 Mn1 O3 88.56(8) . 1_655 ?
O4 Mn1 O3 91.44(8) . 3_576 ?
O4 Mn1 O3 88.56(8) 3_676 3_576 ?
O4 Mn1 O3 91.44(8) 3_676 1_655 ?
O4 Mn1 O4 180.0 . 3_676 ?
O4 Mn1 O5 87.48(9) . 3_676 ?
O4 Mn1 O5 87.48(9) 3_676 . ?
O4 Mn1 O5 92.52(9) . . ?
O4 Mn1 O5 92.52(9) 3_676 3_676 ?
O5 Mn1 O3 88.21(8) 3_676 3_576 ?
O5 Mn1 O3 91.80(8) . 3_576 ?
O5 Mn1 O3 91.79(8) 3_676 1_655 ?
O5 Mn1 O3 88.20(8) . 1_655 ?
O5 Mn1 O5 180.0 3_676 . ?
C9 O3 Mn1 123.44(18) . 1_455 ?
C9 O4 Mn1 129.06(18) . . ?
Mn1 O5 H5A 109.4 . . ?
Mn1 O5 H5B 109.6 . . ?
H5A O5 H5B 104.3 . . ?
C6 N1 C7 125.2(2) . . ?
C6 N1 C8 116.9(2) . . ?
C7 N1 C8 117.6(3) . . ?
C2 C1 H1 119.9 . . ?
C5 C1 H1 119.9 3_666 . ?
C5 C1 C2 120.2(3) 3_666 . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 C7 119.8(3) . . ?
C4 C3 C7 119.9(3) . . ?
C3 C4 C4 119.3(3) . 3_666 ?
C3 C4 C5 121.5(3) . . ?
C5 C4 C4 119.2(3) . 3_666 ?
C1 C5 C4 120.6(3) 3_666 . ?
C1 C5 C6 120.2(3) 3_666 . ?
C4 C5 C6 119.1(3) . . ?
O1 C6 N1 120.9(3) . . ?
O1 C6 C5 121.7(3) . . ?
N1 C6 C5 117.4(2) . . ?
O2 C7 N1 120.5(3) . . ?
O2 C7 C3 123.1(3) . . ?
N1 C7 C3 116.4(3) . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
N1 C8 C9 112.3(2) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
O3 C9 C8 115.9(2) . . ?
O4 C9 O3 125.7(3) . . ?
O4 C9 C8 118.3(2) . . ?

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 H5A O1 0.85 2.02 2.800(3) 150.9 1_655 yes
O5 H5B O3 0.85 2.14 2.837(3) 138.3 3_676 yes

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 O3 C9 O4 -103.4(3) 1_455 . . . ?
Mn1 O3 C9 C8 76.5(3) 1_455 . . . ?
Mn1 O4 C9 O3 6.3(4) . . . . ?
Mn1 O4 C9 C8 -173.6(2) . . . . ?
N1 C8 C9 O3 -171.6(2) . . . . ?
N1 C8 C9 O4 8.3(4) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C1 C2 C3 C7 176.5(3) . . . . ?
C1 C5 C6 O1 -4.0(4) 3_666 . . . ?
C1 C5 C6 N1 176.1(3) 3_666 . . . ?
C2 C3 C4 C4 2.6(5) . . . 3_666 ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C7 O2 -5.8(4) . . . . ?
C2 C3 C7 N1 174.6(3) . . . . ?
C3 C4 C5 C1 -178.0(3) . . . 3_666 ?
C3 C4 C5 C6 3.1(4) . . . . ?
C4 C3 C7 O2 172.9(3) . . . . ?
C4 C3 C7 N1 -6.6(4) . . . . ?
C4 C4 C5 C1 0.9(5) 3_666 . . 3_666 ?
C4 C4 C5 C6 -178.0(3) 3_666 . . . ?
C4 C5 C6 O1 174.9(3) . . . . ?
C4 C5 C6 N1 -5.0(4) . . . . ?
C5 C1 C2 C3 0.2(5) 3_666 . . . ?
C6 N1 C7 O2 -174.8(3) . . . . ?
C6 N1 C7 C3 4.8(4) . . . . ?
C6 N1 C8 C9 76.4(3) . . . . ?
C7 N1 C6 O1 -178.9(3) . . . . ?
C7 N1 C6 C5 0.9(4) . . . . ?
C7 N1 C8 C9 -97.1(3) . . . . ?
C7 C3 C4 C4 -176.1(3) . . . 3_666 ?
C7 C3 C4 C5 2.8(4) . . . . ?
C8 N1 C6 O1 8.1(4) . . . . ?
C8 N1 C6 C5 -172.1(2) . . . . ?
C8 N1 C7 O2 -1.8(4) . . . . ?
C8 N1 C7 C3 177.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2308992'
loop_
_audit_author_name
_audit_author_address
'Shimin Zhang'
;Shanxi Normal University
China
;
_audit_update_record             
;
2023-11-20 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_audit_creation_date             2023-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Mn N2 O10'
_chemical_formula_sum            'C20 H16 Mn N2 O10'
_chemical_formula_weight         499.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6642(5)
_cell_length_b                   8.0332(8)
_cell_length_c                   13.2151(14)
_cell_angle_alpha                103.832(3)
_cell_angle_beta                 96.102(3)
_cell_angle_gamma                94.089(3)
_cell_volume                     475.66(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2699
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.207
_cell_measurement_theta_min      2.624
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             255
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6042
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.418
_diffrn_reflns_theta_min         3.201
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1936
_reflns_number_total             2387
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.055
_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)+(0.0227P)²+0.2883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O5(H5a,H5b)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_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
Mn1 Mn 1.000000 0.000000 0.000000 0.02275(14) Uani 1 2 d S . P . .
O1 O 0.2836(3) 0.46858(18) 0.38802(13) 0.0324(4) Uani 1 1 d . . . . .
O2 O 0.9328(4) 0.7649(2) 0.24915(13) 0.0361(4) Uani 1 1 d . . . . .
O3 O 0.3659(3) 0.18253(18) -0.01300(11) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.7951(3) 0.20914(19) 0.08449(12) 0.0318(4) Uani 1 1 d . . . . .
O5 O 1.2532(3) -0.0278(2) 0.14682(12) 0.0327(4) Uani 1 1 d . . . . .
H5A H 1.407208 -0.073473 0.131904 0.049 Uiso 1 1 d R U . . .
H5B H 1.159148 -0.100086 0.171644 0.049 Uiso 1 1 d R U . . .
N1 N 0.6063(4) 0.6172(2) 0.31758(13) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.5509(4) 0.2573(3) 0.06461(16) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.4753(5) 0.4186(3) 0.13959(17) 0.0297(5) Uani 1 1 d . . . . .
H2A H 0.502336 0.516068 0.108942 0.036 Uiso 1 1 calc R U . . .
H2B H 0.272992 0.404007 0.149734 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6606(5) 0.4552(3) 0.24409(17) 0.0265(5) Uani 1 1 d . . . . .
H3A H 0.624780 0.360086 0.276000 0.032 Uiso 1 1 calc R U . . .
H3B H 0.862895 0.462018 0.232945 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7593(4) 0.7684(3) 0.31203(16) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.7072(4) 0.9305(2) 0.38655(15) 0.0193(4) Uani 1 1 d . . . . .
C6 C 0.5202(4) 0.9237(2) 0.46296(15) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.3736(4) 0.7666(2) 0.46755(15) 0.0180(4) Uani 1 1 d . . . . .
C8 C 0.4118(4) 0.6056(2) 0.38969(16) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.1941(4) 0.7633(3) 0.54288(17) 0.0235(4) Uani 1 1 d . . . . .
H9 H 0.097983 0.659041 0.545237 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1530(4) 0.9146(3) 0.61646(17) 0.0239(4) Uani 1 1 d . . . . .
H10 H 0.031140 0.910069 0.667272 0.029 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 2.2178(14) 2_655 ?
Mn1 O3 2.2178(14) 1_655 ?
Mn1 O4 2.1310(13) 2_755 ?
Mn1 O4 2.1310(13) . ?
Mn1 O5 2.2286(16) . ?
Mn1 O5 2.2286(16) 2_755 ?
O1 C8 1.209(2) . ?
O2 C4 1.217(2) . ?
O3 C1 1.265(2) . ?
O4 C1 1.250(2) . ?
O5 H5A 0.8502 . ?
O5 H5B 0.8500 . ?
N1 C3 1.482(2) . ?
N1 C4 1.386(3) . ?
N1 C8 1.398(3) . ?
C1 C2 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.502(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.486(3) . ?
C5 C6 1.411(3) . ?
C5 C10 1.375(3) 2_676 ?
C6 C6 1.412(3) 2_676 ?
C6 C7 1.410(3) . ?
C7 C8 1.483(2) . ?
C7 C9 1.371(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.403(3) . ?
C10 H10 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 180.00(7) 2_655 1_655 ?
O3 Mn1 O5 87.23(6) 2_655 2_755 ?
O3 Mn1 O5 92.77(6) 2_655 . ?
O3 Mn1 O5 92.77(6) 1_655 2_755 ?
O3 Mn1 O5 87.23(6) 1_655 . ?
O4 Mn1 O3 89.92(5) . 2_655 ?
O4 Mn1 O3 89.92(5) 2_755 1_655 ?
O4 Mn1 O3 90.08(5) . 1_655 ?
O4 Mn1 O3 90.08(5) 2_755 2_655 ?
O4 Mn1 O4 180.00(6) 2_755 . ?
O4 Mn1 O5 91.89(6) 2_755 2_755 ?
O4 Mn1 O5 88.11(6) . 2_755 ?
O4 Mn1 O5 91.89(6) . . ?
O4 Mn1 O5 88.11(6) 2_755 . ?
O5 Mn1 O5 180.0 2_755 . ?
C1 O3 Mn1 122.53(14) . 1_455 ?
C1 O4 Mn1 130.16(13) . . ?
Mn1 O5 H5A 109.3 . . ?
Mn1 O5 H5B 109.3 . . ?
H5A O5 H5B 104.5 . . ?
C4 N1 C3 117.54(16) . . ?
C4 N1 C8 124.77(16) . . ?
C8 N1 C3 117.65(16) . . ?
O3 C1 C2 118.35(18) . . ?
O4 C1 O3 124.84(18) . . ?
O4 C1 C2 116.81(18) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.46(17) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
N1 C3 C2 113.30(17) . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O2 C4 N1 120.09(18) . . ?
O2 C4 C5 122.38(19) . . ?
N1 C4 C5 117.51(17) . . ?
C6 C5 C4 119.48(17) . . ?
C10 C5 C4 120.41(17) 2_676 . ?
C10 C5 C6 120.07(17) 2_676 . ?
C5 C6 C6 119.8(2) . 2_676 ?
C7 C6 C5 121.19(16) . . ?
C7 C6 C6 119.0(2) . 2_676 ?
C6 C7 C8 119.63(17) . . ?
C9 C7 C6 120.07(17) . . ?
C9 C7 C8 120.30(17) . . ?
O1 C8 N1 120.50(18) . . ?
O1 C8 C7 122.22(18) . . ?
N1 C8 C7 117.28(17) . . ?
C7 C9 H9 119.5 . . ?
C7 C9 C10 121.07(18) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C9 119.98(18) 2_676 . ?
C5 C10 H10 120.0 2_676 . ?
C9 C10 H10 120.0 . . ?

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 H5A O3 0.85 2.05 2.786(2) 145.1 2_755 yes
O5 H5B O2 0.85 1.98 2.826(2) 170.4 1_545 yes

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 O3 C1 O4 98.2(2) 1_455 . . . ?
Mn1 O3 C1 C2 -82.3(2) 1_455 . . . ?
Mn1 O4 C1 O3 2.2(3) . . . . ?
Mn1 O4 C1 C2 -177.29(14) . . . . ?
O2 C4 C5 C6 -175.0(2) . . . . ?
O2 C4 C5 C10 2.9(3) . . . 2_676 ?
O3 C1 C2 C3 159.9(2) . . . . ?
O4 C1 C2 C3 -20.5(3) . . . . ?
N1 C4 C5 C6 3.6(3) . . . . ?
N1 C4 C5 C10 -178.51(19) . . . 2_676 ?
C1 C2 C3 N1 176.58(17) . . . . ?
C3 N1 C4 O2 -0.7(3) . . . . ?
C3 N1 C4 C5 -179.34(17) . . . . ?
C3 N1 C8 O1 -3.4(3) . . . . ?
C3 N1 C8 C7 176.04(17) . . . . ?
C4 N1 C3 C2 -86.9(2) . . . . ?
C4 N1 C8 O1 178.8(2) . . . . ?
C4 N1 C8 C7 -1.8(3) . . . . ?
C4 C5 C6 C6 177.2(2) . . . 2_676 ?
C4 C5 C6 C7 -2.3(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 C7 C9 179.70(19) . . . . ?
C6 C6 C7 C8 179.4(2) 2_676 . . . ?
C6 C6 C7 C9 0.2(4) 2_676 . . . ?
C6 C7 C8 O1 -177.5(2) . . . . ?
C6 C7 C8 N1 3.1(3) . . . . ?
C6 C7 C9 C10 -0.1(3) . . . . ?
C7 C9 C10 C5 0.3(3) . . . 2_676 ?
C8 N1 C3 C2 95.1(2) . . . . ?
C8 N1 C4 O2 177.1(2) . . . . ?
C8 N1 C4 C5 -1.5(3) . . . . ?
C8 C7 C9 C10 -179.33(19) . . . . ?
C9 C7 C8 O1 1.8(3) . . . . ?
C9 C7 C8 N1 -177.66(19) . . . . ?
C10 C5 C6 C6 -0.7(4) 2_676 . . 2_676 ?
C10 C5 C6 C7 179.81(19) 2_676 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
