# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_nnhymn_100
_database_code_depnum_ccdc_archive 'CCDC 2064864'
loop_
_audit_author_name
_audit_author_address
'Dorota Kowalska'
;Institute of Low Temperature and Structure Research PAS
Poland
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 Mn O6, C2 H9 N2'
_chemical_formula_sum            'C5 H12 Mn N2 O6'
_chemical_formula_weight         251.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H12 Mn1 N2 O6'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.345(5)
_cell_length_b                   12.124(7)
_cell_length_c                   9.387(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.144(5)
_cell_angle_gamma                90
_cell_volume                     949.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6673
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      29.4740
_cell_measurement_theta_min      2.7090
_shelx_estimated_absorpt_T_max   0.721
_shelx_estimated_absorpt_T_min   0.572
_exptl_absorpt_coefficient_mu    1.398
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             516
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1386
1 0 1 0.2052
-1 0 -1 0.2050
0 -5 -2 0.1726
-1 0 1 0.1328
1 0 -1 0.2409
0 1 0 0.1077

_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.9998 -0.0000 -0.0069 0.0578 -0.0058
0.9998 0.0001 0.9998 0.1129 0.0139 0.0049
-0.9998 -0.0001 -0.9998 -0.1129 -0.0139 -0.0049
0.0001 -4.9992 -1.9998 -0.1403 0.2873 0.0786
-0.9997 0.0001 0.9999 -0.0071 -0.0122 -0.1127
0.9997 -0.0001 -0.9999 0.0071 0.0122 0.1127
-0.0000 0.9998 0.0000 0.0069 -0.0578 0.0058

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15823
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         28.488
_diffrn_reflns_theta_min         2.744
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -32.00   1.00    1.00    --   13.47 178.00   0.00   45
  2  ω    -77.00 -32.00   1.00    1.00    --   13.47 178.00 150.00   45
  3  ω    -99.00  22.00   1.00    1.00    --  -14.56 -77.00 -90.00  121
  4  ω    -25.00  57.00   1.00    1.00    --   13.47 -99.00 150.00   82
  5  ω    -93.00 -68.00   1.00    1.00    --  -14.56 -57.00 -30.00   25
  6  ω   -105.00 -32.00   1.00    1.00    --  -14.56 178.00-120.00   73
  7  ω    -25.00  29.00   1.00    1.00    --  -14.56 -99.00 -30.00   54
  8  ω    -94.00  17.00   1.00    1.00    --  -14.56 -37.00  90.00  111
  9  ω    -47.00  63.00   1.00    1.00    --  -14.56  57.00-120.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0600245000
_diffrn_orient_matrix_UB_12      0.0069016000
_diffrn_orient_matrix_UB_13      0.0528958000
_diffrn_orient_matrix_UB_21      0.0130700000
_diffrn_orient_matrix_UB_22      -0.0578026000
_diffrn_orient_matrix_UB_23      0.0008506000
_diffrn_orient_matrix_UB_31      0.0587936000
_diffrn_orient_matrix_UB_32      0.0058386000
_diffrn_orient_matrix_UB_33      -0.0539107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2188
_reflns_number_total             2360
_reflns_odcompleteness_completeness 99.85
_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.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1997)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+1.0358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0934
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6165(17)
 0.3835(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Rotating group:
 N1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 N2(H2)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3)
3.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1C,H1D,H1E)
;
_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 0.21794(5) 0.75589(3) 0.73447(5) 0.01366(12) Uani 1 1 d . . . . .
O4 O 0.0458(3) 0.81569(17) 0.8897(2) 0.0202(4) Uani 1 1 d . . . . .
O5 O 0.0366(3) 0.82186(17) 0.5869(2) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.1112(2) 0.59093(14) 0.7315(2) 0.0183(4) Uani 1 1 d . . . . .
O6 O 0.3520(2) 0.90991(14) 0.7476(2) 0.0193(4) Uani 1 1 d . . . . .
N1 N 0.7999(3) 0.36419(18) 0.7369(3) 0.0218(5) Uani 1 1 d . . . . .
H1A H 0.913951 0.387364 0.723339 0.026 Uiso 1 1 d GR . . . .
H1B H 0.752100 0.346033 0.643733 0.026 Uiso 1 1 d GR . . . .
O2 O 0.3875(3) 0.68774(17) 0.8893(2) 0.0222(5) Uani 1 1 d . . . . .
C5 C -0.0350(3) 0.7691(3) 0.4892(4) 0.0156(6) Uani 1 1 d . . . . .
H5 H -0.029739 0.692557 0.491930 0.019 Uiso 1 1 calc R . . . .
O1 O 0.3532(3) 0.70158(17) 0.5487(2) 0.0208(4) Uani 1 1 d . . . . .
C4 C -0.0190(4) 0.7682(3) 0.9922(4) 0.0176(6) Uani 1 1 d . . . . .
H4 H 0.031374 0.705958 1.029127 0.021 Uiso 1 1 calc R . . . .
N2 N 0.7023(3) 0.45587(19) 0.7839(3) 0.0198(5) Uani 1 1 d . . . . .
H2 H 0.597364 0.426075 0.810525 0.024 Uiso 1 1 calc R . . . .
C3 C 0.1964(3) 0.50605(19) 0.7275(3) 0.0173(5) Uani 1 1 d . . . . .
H3 H 0.303884 0.514859 0.704311 0.021 Uiso 1 1 calc R . . . .
C2 C 0.7750(4) 0.5044(2) 0.9145(3) 0.0233(6) Uani 1 1 d . . . . .
H2A H 0.790881 0.447578 0.984260 0.035 Uiso 1 1 calc GR . . . .
H2B H 0.704735 0.559820 0.952293 0.035 Uiso 1 1 calc GR . . . .
H2C H 0.876258 0.537260 0.891108 0.035 Uiso 1 1 calc GR . . . .
C1 C 0.6745(4) 0.5417(3) 0.6730(3) 0.0274(7) Uani 1 1 d . . . . .
H1C H 0.773580 0.578687 0.652619 0.041 Uiso 1 1 calc GR . . . .
H1D H 0.597648 0.594288 0.707206 0.041 Uiso 1 1 calc GR . . . .
H1E H 0.634479 0.507540 0.587851 0.041 Uiso 1 1 calc GR . . . .


_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 O4 2.173(2) . ?
Mn1 O5 2.199(2) . ?
Mn1 O3 2.190(2) . ?
Mn1 O6 2.180(2) . ?
Mn1 O2 2.188(2) . ?
Mn1 O1 2.181(2) . ?
O4 C4 1.246(4) . ?
O5 C5 1.267(4) . ?
O3 C3 1.251(3) . ?
O6 C3 1.256(3) 2_556 ?
N1 N2 1.447(3) . ?
O2 C5 1.252(4) 4_676 ?
O1 C4 1.248(4) 4_675 ?
N2 C2 1.488(4) . ?
N2 C1 1.490(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
O4 Mn1 O5 81.16(8) . . ?
O4 Mn1 O3 92.50(8) . . ?
O4 Mn1 O6 90.94(8) . . ?
O4 Mn1 O2 96.20(9) . . ?
O4 Mn1 O1 168.79(9) . . ?
O3 Mn1 O5 92.58(8) . . ?
O6 Mn1 O5 94.38(8) . . ?
O6 Mn1 O3 172.64(7) . . ?
O6 Mn1 O2 87.41(8) . . ?
O6 Mn1 O1 92.14(8) . . ?
O2 Mn1 O5 176.82(8) . . ?
O2 Mn1 O3 85.75(8) . . ?
O1 Mn1 O5 87.86(9) . . ?
O1 Mn1 O3 85.72(8) . . ?
O1 Mn1 O2 94.70(10) . . ?
C4 O4 Mn1 130.7(2) . . ?
C5 O5 Mn1 126.5(2) . . ?
C3 O3 Mn1 121.37(16) . . ?
C3 O6 Mn1 129.81(17) 2_556 . ?
C5 O2 Mn1 132.2(2) 4_676 . ?
O2 C5 O5 125.0(3) 4_575 . ?
C4 O1 Mn1 134.1(2) 4_675 . ?
O4 C4 O1 124.4(3) . 4_576 ?
N1 N2 C2 109.0(2) . . ?
N1 N2 C1 114.2(2) . . ?
C2 N2 C1 111.2(2) . . ?
O3 C3 O6 125.1(2) . 2_546 ?

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
N1 H1A O6 1.00 1.99 2.961(3) 162.6 2_646 yes
N1 H1B O1 0.99 2.09 3.072(3) 176.6 3_666 yes
N2 H2 O4 0.98 2.60 3.133(3) 114.5 2_546 yes
N2 H2 O5 0.98 1.94 2.846(3) 151.8 2_546 yes
C2 H2A O2 0.96 2.52 3.267(4) 135.2 3_667 yes
C2 H2B O5 0.96 2.37 3.321(4) 169.1 4_676 yes
C2 H2C O3 0.96 2.55 3.456(4) 156.5 1_655 yes

_olex2_date_sample_data_collection 2020-04-05
_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 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.913
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6165(17)
2 0.3835(17)

####################################################################### 
# 
# 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_nnhymn_300
_database_code_depnum_ccdc_archive 'CCDC 2064865'
loop_
_audit_author_name
_audit_author_address
'Dorota Kowalska'
;Institute of Low Temperature and Structure Research PAS
Poland
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_nnhymn_300          
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: Disordered atoms are not taken into account in the tests and the struc
;
_vrf_PLAT112_nnhymn_300          
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit
RESPONSE: Disordered atoms are not taken into account in the tests and the structure has disordered atoms.
;
_vrf_PLAT113_nnhymn_300          
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check
RESPONSE: Disordered atoms are not taken into account in the tests and the structure has disordered atoms.
;
_vrf_PLAT241_nnhymn_300          
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         O1 Check
RESPONSE: There is a disorder in the structure and thus the alert does not indicate an incorrect atom-type assignment.
;
_vrf_PLAT241_nnhymn_300_2        
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         O4 Check
RESPONSE: There is a disorder in the structure and thus the alert does not indicate an incorrect atom-type assignment.
;
_vrf_PLAT242_nnhymn_300          
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Mn1 Check
RESPONSE: There is a disorder in the structure and thus the alert does not indicate an incorrect atom-type assignment.
;
_vrf_PLAT242_nnhymn_300_2        
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Mn2 Check
RESPONSE: There is a disorder in the structure and thus the alert does not indicate an incorrect atom-type assignment.
;
_vrf_PLAT242_nnhymn_300_3        
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         N2 Check
RESPONSE: N2 atom belongs to the disordered ion in which N2 atom is the only one non-hydrogen atom which is not disordered.
;
_vrf_PLAT420_nnhymn_300          
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check
RESPONSE: The position of N1 atoms is disordered (it is occupied by N and C atoms).
;
_vrf_PLAT420_nnhymn_300_2        
;
PROBLEM: D-H Without Acceptor       N2A      --H2A      .     Please Check
RESPONSE: The position of N2A atoms is disordered (it is occupied by N and C atoms).
;
_vrf_PLAT420_nnhymn_300_3        
;
PROBLEM: D-H Without Acceptor       N2A      --H2C      .     Please Check
RESPONSE: The position of N2A atoms is disordered (it is occupied by N and C atoms).
;
# Added during the CSD deposition process: Wednesday 24 February 2021 12:14 PM
# end Validation Reply Form

_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 Mn O6, C2 H9 N2'
_chemical_formula_sum            'C5 H12 Mn N2 O6'
_chemical_formula_weight         251.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         C5H12Mn1N2O6
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.554(3)
_cell_length_b                   9.207(3)
_cell_length_c                   12.387(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.432(3)
_cell_angle_gamma                90
_cell_volume                     972.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5626
_cell_measurement_temperature    299.92(15)
_cell_measurement_theta_max      29.4240
_cell_measurement_theta_min      2.8120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.365
_exptl_absorpt_correction_T_max  0.734
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             516
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1386
-1 -1 0 0.2050
0 -2 5 0.1726
0 0 -1 0.1077
1 -1 0 0.2409
-1 1 0 0.1328
1 1 0 0.2052

_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.246
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0016 0.0000 0.9992 -0.0058 0.0570 -0.0030
-0.9993 -0.9995 0.0020 -0.1119 -0.0181 -0.0011
0.0080 -1.9990 4.9959 -0.1355 0.2800 0.0964
-0.0016 -0.0000 -0.9992 0.0058 -0.0570 0.0030
0.9992 -0.9997 -0.0020 0.0056 0.0130 0.1124
-0.9992 0.9997 0.0020 -0.0056 -0.0130 -0.1124
0.9993 0.9995 -0.0020 0.1119 0.0181 0.0011

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15551
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         29.508
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.92(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -32.00   1.00    1.00    --   13.47 178.00 120.00   45
  2  ω    -77.00 -32.00   1.00    1.00    --   13.47 178.00 150.00   45
  3  ω   -105.00 -32.00   1.00    1.00    --  -14.56 178.00 -30.00   73
  4  ω    -99.00  22.00   1.00    1.00    --  -14.56 -77.00-120.00  121
  5  ω    -18.00  93.00   1.00    1.00    --   13.47  37.00-180.00  111
  6  ω    -18.00  93.00   1.00    1.00    --   13.47  37.00  30.00  111
  7  ω   -105.00 -72.00   1.00    1.00    --  -14.56 178.00-120.00   33
  8  ω    -47.00  63.00   1.00    1.00    --  -14.56  57.00-120.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0587494000
_diffrn_orient_matrix_UB_12      0.0531595000
_diffrn_orient_matrix_UB_13      -0.0059429000
_diffrn_orient_matrix_UB_21      0.0156632000
_diffrn_orient_matrix_UB_22      0.0025571000
_diffrn_orient_matrix_UB_23      0.0570364000
_diffrn_orient_matrix_UB_31      0.0567648000
_diffrn_orient_matrix_UB_32      -0.0556967000
_diffrn_orient_matrix_UB_33      -0.0030723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1861
_reflns_number_total             2510
_reflns_odcompleteness_completeness 99.86
_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.
 
 _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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1997)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0193(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.033
_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)+(0.0316P)²+0.9387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0852
_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, All N(H) groups, All N(H,H,H) groups
2. Shared sites
{C2, N2A, C2B}
{C1A, N1, C1B}
{C1, C3A, N3B}
3. Restrained distances
 N2-H2
 0.96 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(N2A) = Uanis(C2B)
Uanis(C1A) = Uanis(N1) = Uanis(C1B)
Uanis(C1) = Uanis(C3A) = Uanis(N3B)
5. Others
 Fixed Sof: N1(0.33333) H1C(0.66667) C2(0.33333) H2A(0.66667) C1(0.33333)
 H1F(0.66667) C1A(0.33333) N2A(0.33333) C3A(0.33333) C1B(0.33333) C2B(0.33333)
 N3B(0.33333)
6.a Rotating group:
 N2(H2)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
6.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C1(H1D,H1E,H1F)
;
_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 0.000000 0.500000 1.000000 0.01974(13) Uani 1 2 d S T P . .
Mn2 Mn 0.500000 1.000000 1.000000 0.01953(13) Uani 1 2 d S T P . .
O1 O 0.1898(2) 0.63369(19) 0.94732(13) 0.0437(4) Uani 1 1 d . . . . .
O2 O 0.12468(19) 0.30585(17) 0.95221(13) 0.0404(4) Uani 1 1 d . . . . .
O3 O -0.11011(19) 0.50321(17) 0.83469(12) 0.0364(4) Uani 1 1 d . . . . .
O4 O 0.35834(19) 0.81458(18) 0.94649(13) 0.0424(4) Uani 1 1 d . . . . .
O5 O 0.69994(17) 0.86650(16) 1.06431(12) 0.0318(3) Uani 1 1 d . . . . .
O6 O 0.60313(19) 0.99939(18) 0.84378(12) 0.0383(4) Uani 1 1 d . . . . .
C3 C -0.0455(3) 0.5147(2) 0.74950(16) 0.0305(5) Uani 1 1 d . . . . .
H3 H 0.060584 0.537978 0.756794 0.037 Uiso 1 1 calc R . . . .
C4 C 0.2718(3) 0.7298(2) 0.99019(17) 0.0329(5) Uani 1 1 d . . . . .
H4 H 0.268196 0.739878 1.064656 0.039 Uiso 1 1 calc R . . . .
C5 C 0.2504(2) 0.2473(2) 0.97748(17) 0.0305(4) Uani 1 1 d . . . . .
H5 H 0.314851 0.290568 1.032253 0.037 Uiso 1 1 calc R . . . .
N2 N 0.4480(2) 0.5132(2) 0.69743(17) 0.0414(5) Uani 1 1 d D . . . .
H2 H 0.358105 0.555611 0.655067 0.062 Uiso 1 1 d DGR . . A .
N1 N 0.5430(3) 0.4439(4) 0.6229(3) 0.0657(9) Uani 0.3333 1 d . . . A 1
H1A H 0.499771 0.359569 0.601978 0.099 Uiso 1 1 calc GR . . . .
H1B H 0.638335 0.428159 0.654824 0.099 Uiso 1 1 calc GR . . . .
H1C H 0.550290 0.500761 0.565393 0.099 Uiso 0.6667 1 calc GR . . . .
C2 C 0.3914(5) 0.4116(4) 0.7775(3) 0.0913(12) Uani 0.3333 1 d . . . A 1
H2A H 0.335840 0.333268 0.740706 0.137 Uiso 0.6667 1 calc GR . . . .
H2B H 0.322491 0.461857 0.822440 0.137 Uiso 1 1 calc GR . . . .
H2C H 0.479125 0.373582 0.821747 0.137 Uiso 1 1 calc GR . . . .
C1 C 0.5315(4) 0.6369(3) 0.7514(2) 0.0640(8) Uani 0.3333 1 d . . . A 1
H1D H 0.620268 0.601728 0.795943 0.096 Uiso 1 1 calc GR . . . .
H1E H 0.461923 0.687513 0.795612 0.096 Uiso 1 1 calc GR . . . .
H1F H 0.566519 0.701923 0.697675 0.096 Uiso 0.6667 1 calc GR . . . .
C1A C 0.5430(3) 0.4439(4) 0.6229(3) 0.0657(9) Uani 0.3333 1 d . . . A 2
N2A N 0.3914(5) 0.4116(4) 0.7775(3) 0.0913(12) Uani 0.3333 1 d . . . A 2
C3A C 0.5315(4) 0.6369(3) 0.7514(2) 0.0640(8) Uani 0.3333 1 d . . . A 2
C1B C 0.5430(3) 0.4439(4) 0.6229(3) 0.0657(9) Uani 0.3333 1 d . . . A 3
C2B C 0.3914(5) 0.4116(4) 0.7775(3) 0.0913(12) Uani 0.3333 1 d . . . A 3
N3B N 0.5315(4) 0.6369(3) 0.7514(2) 0.0640(8) Uani 0.3333 1 d . . . A 3


_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 2.1774(16) 3_567 ?
Mn1 O1 2.1774(16) . ?
Mn1 O2 2.1865(16) . ?
Mn1 O2 2.1865(16) 3_567 ?
Mn1 O3 2.1870(16) . ?
Mn1 O3 2.1870(16) 3_567 ?
Mn2 O4 2.1675(16) . ?
Mn2 O4 2.1674(16) 3_677 ?
Mn2 O5 2.2045(15) 3_677 ?
Mn2 O5 2.2045(15) . ?
Mn2 O6 2.1879(16) . ?
Mn2 O6 2.1878(16) 3_677 ?
O1 C4 1.224(3) . ?
O2 C5 1.222(2) . ?
O3 C3 1.233(3) . ?
O4 C4 1.230(3) . ?
O5 C5 1.257(2) 3_667 ?
O6 C3 1.229(3) 2_556 ?
N2 N1 1.427(3) . ?
N2 C2 1.472(4) . ?
N2 C1 1.477(4) . ?
N2 C1A 1.427(3) . ?
N2 N2A 1.472(4) . ?
N2 C3A 1.477(4) . ?
N2 C1B 1.427(3) . ?
N2 C2B 1.472(4) . ?
N2 N3B 1.477(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
O1 Mn1 O1 180.0 3_567 . ?
O1 Mn1 O2 89.45(7) . . ?
O1 Mn1 O2 90.55(7) . 3_567 ?
O1 Mn1 O2 90.55(7) 3_567 . ?
O1 Mn1 O2 89.45(7) 3_567 3_567 ?
O1 Mn1 O3 89.37(6) . . ?
O1 Mn1 O3 90.64(6) . 3_567 ?
O1 Mn1 O3 89.36(6) 3_567 3_567 ?
O1 Mn1 O3 90.63(6) 3_567 . ?
O2 Mn1 O2 180.0 . 3_567 ?
O2 Mn1 O3 93.36(6) 3_567 . ?
O2 Mn1 O3 86.64(6) . . ?
O2 Mn1 O3 93.36(6) . 3_567 ?
O2 Mn1 O3 86.64(6) 3_567 3_567 ?
O3 Mn1 O3 180.00(8) . 3_567 ?
O4 Mn2 O4 180.00(7) 3_677 . ?
O4 Mn2 O5 85.92(7) . 3_677 ?
O4 Mn2 O5 94.08(7) 3_677 3_677 ?
O4 Mn2 O5 94.08(7) . . ?
O4 Mn2 O5 85.92(7) 3_677 . ?
O4 Mn2 O6 88.94(6) 3_677 3_677 ?
O4 Mn2 O6 91.06(6) 3_677 . ?
O4 Mn2 O6 88.95(6) . . ?
O4 Mn2 O6 91.06(6) . 3_677 ?
O5 Mn2 O5 180.00(5) . 3_677 ?
O6 Mn2 O5 92.08(6) . 3_677 ?
O6 Mn2 O5 87.92(6) . . ?
O6 Mn2 O5 87.92(6) 3_677 3_677 ?
O6 Mn2 O5 92.08(6) 3_677 . ?
O6 Mn2 O6 180.0 3_677 . ?
C4 O1 Mn1 133.94(15) . . ?
C5 O2 Mn1 136.83(15) . . ?
C3 O3 Mn1 127.84(15) . . ?
C4 O4 Mn2 134.97(15) . . ?
C5 O5 Mn2 126.38(14) 3_667 . ?
C3 O6 Mn2 132.19(15) 2_556 . ?
O6 C3 O3 128.4(2) 2_546 . ?
O1 C4 O4 127.7(2) . . ?
O2 C5 O5 125.5(2) . 3_667 ?
N1 N2 C2 112.7(3) . . ?
N1 N2 C1 111.0(2) . . ?
C2 N2 C1 110.9(3) . . ?
C1A N2 N2A 112.7(3) . . ?
C1A N2 C3A 111.0(2) . . ?
N2A N2 C3A 110.9(3) . . ?
C1B N2 C2B 112.7(3) . . ?
C1B N2 N3B 111.0(2) . . ?
C2B N2 N3B 110.9(3) . . ?

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
N2 H2 O5 0.98 1.84 2.812(3) 174.6 4_575 yes
N1 H1B O6 0.89 2.31 3.066(3) 143.3 2_646 yes
C2 H2B O1 0.96 2.54 3.484(5) 167.4 . yes
C1 H1D O3 0.96 2.49 3.390(3) 156.0 1_655 yes
C1 H1E O4 0.96 2.43 3.356(3) 162.1 . yes
C1 H1F O2 0.96 2.56 3.169(4) 121.3 2_556 yes

_olex2_date_sample_data_collection 2020-04-05
_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 1.061
_oxdiff_exptl_absorpt_empirical_full_min 0.936
