# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 2004014'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Mn N10 O'
_chemical_formula_weight         421.34
_chemical_absolute_configuration ?
_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'
N N 0.0061 0.0033 '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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.9085(3)
_cell_length_b                   8.67119(14)
_cell_length_c                   13.4009(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1964.80(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    119.99(12)
_cell_measurement_reflns_used    23117
_cell_measurement_theta_min      2.8400
_cell_measurement_theta_max      29.1360

_exptl_absorpt_coefficient_mu    0.701
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_absorpt_correction_T_min  0.96034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.973
_oxdiff_exptl_absorpt_empirical_full_max 1.054
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      119.99(12)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.409


_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000


_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3866
_reflns_number_total             4017
_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_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ?
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(5)
_refine_ls_extinction_coef       0.0025(4)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.073
_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)+(0.0257P)²+0.2890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0507
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_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
Mn Mn 0.28208(2) 0.33460(3) 0.61898(3) 0.01250(9) Uani 1 1 d . . . . .
O1 O 0.28403(10) 0.31844(19) 0.78041(15) 0.0199(5) Uani 1 1 d . . . . .
H1 H 0.244839 0.257809 0.806767 0.030 Uiso 1 1 d R U . . .
H2 H 0.273863 0.411307 0.809379 0.030 Uiso 1 1 d R U . . .
N1 N 0.27842(12) 0.3453(2) 0.44479(18) 0.0187(5) Uani 1 1 d . . . . .
N2 N 0.31835(13) 0.5839(2) 0.35723(15) 0.0272(5) Uani 1 1 d . . . . .
N3 N 0.22833(13) 0.1091(2) 0.36285(15) 0.0286(5) Uani 1 1 d . . . . .
N4 N 0.40960(10) 0.3725(2) 0.60620(18) 0.0237(4) Uani 1 1 d . . . . .
N5 N 0.53443(13) 0.3062(3) 0.52398(17) 0.0394(6) Uani 1 1 d . . . . .
N7 N 0.65455(10) 0.2137(2) 0.60783(17) 0.0239(4) Uani 1 1 d . . . . .
N8 N 0.26083(10) 0.58145(18) 0.61342(17) 0.0185(4) Uani 1 1 d . . . . .
N9 N 0.24176(16) 0.8415(2) 0.54631(19) 0.0386(6) Uani 1 1 d . . . . .
N11 N 0.29950(11) 1.08437(19) 0.60557(17) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.29921(14) 0.4696(3) 0.39373(17) 0.0197(5) Uani 1 1 d . . . . .
C2 C 0.25218(14) 0.2222(3) 0.39594(17) 0.0200(5) Uani 1 1 d . . . . .
C3 C 0.46947(14) 0.3384(2) 0.57127(18) 0.0199(5) Uani 1 1 d . . . . .
C4 C 0.59699(13) 0.2593(3) 0.57271(18) 0.0206(5) Uani 1 1 d . . . . .
C5 C 0.25501(13) 0.7065(2) 0.58572(17) 0.0188(5) Uani 1 1 d . . . . .
C6 C 0.27367(14) 0.9671(2) 0.58163(19) 0.0213(5) Uani 1 1 d . . . . .
N1a N 0.52002(12) 0.8240(2) 0.41379(14) 0.0221(4) Uani 1 1 d . . . . .
C7 C 0.50161(14) 1.0234(3) 0.27574(16) 0.0212(5) Uani 1 1 d . . . . .
C8 C 0.42546(14) 1.0806(3) 0.26275(19) 0.0236(5) Uani 1 1 d . . . . .
H15 H 0.382219 1.015043 0.269267 0.028 Uiso 1 1 calc R U . . .
C9 C 0.41372(14) 1.2358(3) 0.24000(17) 0.0262(5) Uani 1 1 d . . . . .
H7 H 0.362696 1.273892 0.232018 0.031 Uiso 1 1 calc R U . . .
C10 C 0.47784(16) 1.3329(3) 0.22934(19) 0.0290(6) Uani 1 1 d . . . . .
H10 H 0.469850 1.436439 0.214399 0.035 Uiso 1 1 calc R U . . .
C11 C 0.55419(15) 1.2768(3) 0.24078(19) 0.0307(6) Uani 1 1 d . . . . .
H11 H 0.597359 1.342310 0.233493 0.037 Uiso 1 1 calc R U . . .
C12 C 0.56552(16) 1.1226(4) 0.26312(19) 0.0280(6) Uani 1 1 d . . . . .
H3 H 0.616682 1.084663 0.269817 0.034 Uiso 1 1 calc R U . . .
C13 C 0.51414(15) 0.8559(3) 0.30198(18) 0.0248(5) Uani 1 1 d . . . . .
H8 H 0.562331 0.820508 0.270087 0.030 Uiso 1 1 calc R U . . .
H9 H 0.470663 0.796212 0.274850 0.030 Uiso 1 1 calc R U . . .
C14 C 0.59070(16) 0.9027(3) 0.4573(2) 0.0282(6) Uani 1 1 d . . . . .
H4 H 0.637576 0.867688 0.423814 0.042 Uiso 1 1 calc R U . . .
H5 H 0.594388 0.878891 0.527076 0.042 Uiso 1 1 calc R U . . .
H6 H 0.585535 1.012218 0.448861 0.042 Uiso 1 1 calc R U . . .
C15 C 0.52932(17) 0.6534(3) 0.4275(2) 0.0330(6) Uani 1 1 d . . . . .
H12 H 0.575652 0.618927 0.392655 0.049 Uiso 1 1 calc R U . . .
H13 H 0.483630 0.601538 0.401425 0.049 Uiso 1 1 calc R U . . .
H14 H 0.534633 0.630553 0.497296 0.049 Uiso 1 1 calc R U . . .
C16 C 0.44682(17) 0.8773(4) 0.4669(2) 0.0311(6) Uani 1 1 d . . . . .
H16 H 0.450115 0.849541 0.536133 0.047 Uiso 1 1 calc R U . . .
H17 H 0.401284 0.829135 0.437571 0.047 Uiso 1 1 calc R U . . .
H18 H 0.442239 0.987243 0.460986 0.047 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
Mn O1 2.168(2) . ?
Mn N1 2.337(2) . ?
Mn N4 2.1877(18) . ?
Mn N7 2.2017(18) 3_455 ?
Mn N8 2.1717(16) . ?
Mn N11 2.1971(17) 1_545 ?
O1 H1 0.9167 . ?
O1 H2 0.9103 . ?
N1 C1 1.325(3) . ?
N1 C2 1.328(3) . ?
N2 C1 1.151(3) . ?
N3 C2 1.150(3) . ?
N4 C3 1.154(3) . ?
N5 C4 1.308(3) . ?
N7 C4 1.151(3) . ?
N8 C5 1.150(3) . ?
N9 C5 1.303(3) . ?
N9 C6 1.304(3) . ?
N11 C6 1.152(3) . ?
C3 N5 1.298(3) . ?
N1a C13 1.527(3) . ?
N1a C14 1.495(3) . ?
N1a C15 1.498(3) . ?
N1a C16 1.501(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.392(4) . ?
C7 C13 1.509(3) . ?
C8 H15 0.9300 . ?
C9 C8 1.394(4) . ?
C9 H7 0.9300 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C11 1.383(4) . ?
C12 H3 0.9300 . ?
C13 H8 0.9700 . ?
C13 H9 0.9700 . ?
C14 H4 0.9600 . ?
C14 H5 0.9600 . ?
C14 H6 0.9600 . ?
C15 H12 0.9600 . ?
C15 H13 0.9600 . ?
C15 H14 0.9600 . ?
C16 H16 0.9600 . ?
C16 H17 0.9600 . ?
C16 H18 0.9600 . ?

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 Mn N1 178.43(6) . . ?
O1 Mn N4 94.18(7) . . ?
O1 Mn N7 94.03(8) . 3_455 ?
O1 Mn N8 95.77(8) . . ?
O1 Mn N11 90.90(7) . 1_545 ?
N4 Mn N1 86.67(8) . . ?
N4 Mn N7 171.30(9) . 3_455 ?
N4 Mn N11 90.56(7) . 1_545 ?
N7 Mn N1 85.06(8) 3_455 . ?
N8 Mn N1 85.54(8) . . ?
N8 Mn N4 90.71(6) . . ?
N8 Mn N7 91.33(6) . 3_455 ?
N8 Mn N11 173.10(9) . 1_545 ?
N11 Mn N1 87.76(8) 1_545 . ?
N11 Mn N7 86.43(7) 1_545 3_455 ?
Mn O1 H1 114.2 . . ?
Mn O1 H2 111.4 . . ?
H1 O1 H2 101.9 . . ?
C1 N1 Mn 122.76(16) . . ?
C1 N1 C2 119.2(2) . . ?
C2 N1 Mn 118.00(16) . . ?
C3 N4 Mn 149.09(19) . . ?
C3 N5 C4 120.5(2) . . ?
C4 N7 Mn 157.11(19) . 3 ?
C5 N8 Mn 162.6(2) . . ?
C5 N9 C6 122.1(2) . . ?
C6 N11 Mn 147.52(18) . 1_565 ?
N2 C1 N1 174.0(3) . . ?
N3 C2 N1 173.1(3) . . ?
N4 C3 N5 174.4(3) . . ?
N7 C4 N5 174.1(3) . . ?
N8 C5 N9 172.7(2) . . ?
N11 C6 N9 174.1(3) . . ?
C14 N1a C13 110.58(19) . . ?
C14 N1a C15 108.6(2) . . ?
C14 N1a C16 109.5(2) . . ?
C15 N1a C13 107.85(18) . . ?
C15 N1a C16 109.4(2) . . ?
C16 N1a C13 110.84(19) . . ?
C8 C7 C13 120.1(2) . . ?
C12 C7 C8 118.9(2) . . ?
C12 C7 C13 121.0(2) . . ?
C7 C8 H15 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H15 119.9 . . ?
C8 C9 H7 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H7 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 H3 119.5 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H3 119.5 . . ?
N1a C13 H8 108.7 . . ?
N1a C13 H9 108.7 . . ?
C7 C13 N1a 114.36(18) . . ?
C7 C13 H8 108.7 . . ?
C7 C13 H9 108.7 . . ?
H8 C13 H9 107.6 . . ?
N1a C14 H4 109.5 . . ?
N1a C14 H5 109.5 . . ?
N1a C14 H6 109.5 . . ?
H4 C14 H5 109.5 . . ?
H4 C14 H6 109.5 . . ?
H5 C14 H6 109.5 . . ?
N1a C15 H12 109.5 . . ?
N1a C15 H13 109.5 . . ?
N1a C15 H14 109.5 . . ?
H12 C15 H13 109.5 . . ?
H12 C15 H14 109.5 . . ?
H13 C15 H14 109.5 . . ?
N1a C16 H16 109.5 . . ?
N1a C16 H17 109.5 . . ?
N1a C16 H18 109.5 . . ?
H16 C16 H17 109.5 . . ?
H16 C16 H18 109.5 . . ?
H17 C16 H18 109.5 . . ?

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
O1 H1 N2 0.92 1.97 2.863(3) 164.7 4_545 yes
O1 H2 N3 0.91 1.86 2.760(3) 169.8 4 yes

