# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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 1992055'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2022-02-19 deposited with the CCDC.	2022-10-20 downloaded from the CCDC.
;
_audit_creation_date             2022-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Mn N5 O14'
_chemical_formula_sum            'C21 H15 Mn N5 O14'
_chemical_formula_weight         616.32
_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 0.0181 0.0091 '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 -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   19.6232(8)
_cell_length_b                   13.1888(5)
_cell_length_c                   8.6608(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.265(3)
_cell_angle_gamma                90
_cell_volume                     2223.48(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17690
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.55
_cell_measurement_theta_min      4.05
_shelx_estimated_absorpt_T_max   0.659
_shelx_estimated_absorpt_T_min   0.221
_exptl_absorpt_coefficient_mu    5.688
_exptl_absorpt_correction_T_max  0.2484
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12169
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.148
_diffrn_reflns_theta_min         4.049
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1929
_reflns_number_total             2122
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.035
_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)+(0.0747P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0952
_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) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
 C1-H1
 1.888718 with sigma of 0.02
 Mn1-H1
 2.941281 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9), C11(H11)
;
_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 0.07622(3) 0.250000 0.01929(15) Uani 1 2 d DS T P . .
O1 O 0.55277(7) 0.13452(10) 0.48745(16) 0.0228(3) Uani 1 1 d D . . . .
H1 H 0.5328(11) 0.1109(13) 0.5648(15) 0.034 Uiso 1 1 d D U . . .
O2 O 0.40842(7) 0.07944(9) 0.37142(16) 0.0226(3) Uani 1 1 d . . . . .
O3 O 0.44905(7) 0.06409(9) 0.62427(16) 0.0216(3) Uani 1 1 d . . . . .
O4 O 0.15415(8) 0.08243(11) 0.24139(17) 0.0299(3) Uani 1 1 d . . . . .
O5 O 0.09638(7) 0.16363(11) 0.39923(18) 0.0318(3) Uani 1 1 d . . . . .
O6 O 0.18523(7) 0.12617(13) 0.94225(17) 0.0354(4) Uani 1 1 d . . . . .
O7 O 0.29419(7) 0.14644(11) 1.01137(17) 0.0315(3) Uani 1 1 d . . . . .
N1 N 0.500000 0.24899(16) 0.250000 0.0208(5) Uani 1 2 d S T P . .
N2 N 0.14907(8) 0.12313(12) 0.36570(19) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.24438(8) 0.13470(12) 0.91318(19) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.55517(10) 0.24070(14) 0.5179(2) 0.0232(4) Uani 1 1 d D . . . .
H1A H 0.603337 0.261263 0.550813 0.028 Uiso 1 1 calc R U . . .
H1B H 0.528220 0.255912 0.604260 0.028 Uiso 1 1 calc R U . . .
C2 C 0.52693(9) 0.30078(14) 0.3768(2) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.52863(9) 0.40649(14) 0.3800(2) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.549119 0.441469 0.469958 0.029 Uiso 1 1 calc R U . . .
C4 C 0.500000 0.4595(2) 0.250000 0.0258(6) Uani 1 2 d S T P . .
H4 H 0.500001 0.531534 0.249998 0.031 Uiso 1 2 calc R U P . .
C5 C 0.40175(10) 0.07874(13) 0.5133(2) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.33048(9) 0.09973(14) 0.5562(2) 0.0213(4) Uani 1 1 d . . . . .
C7 C 0.27444(9) 0.10607(14) 0.4406(2) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.280347 0.099379 0.333923 0.026 Uiso 1 1 calc R U . . .
C8 C 0.20967(9) 0.12239(14) 0.4849(2) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.19820(10) 0.13417(14) 0.6375(2) 0.0237(4) Uani 1 1 d . . . . .
H9 H 0.153561 0.146165 0.665057 0.028 Uiso 1 1 calc R U . . .
C10 C 0.25552(10) 0.12754(14) 0.7486(2) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.32122(9) 0.11018(14) 0.7124(2) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.359096 0.105498 0.792092 0.026 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 O1 2.3139(13) . ?
Mn1 O1 2.3139(13) 2_655 ?
Mn1 O2 2.1944(13) . ?
Mn1 O2 2.1945(13) 2_655 ?
Mn1 O3 2.3097(13) 5_656 ?
Mn1 O3 2.3097(13) 6 ?
Mn1 N1 2.279(2) . ?
O1 H1 0.875(9) . ?
O1 C1 1.425(2) . ?
O2 C5 1.253(2) . ?
O3 C5 1.263(2) . ?
O4 N2 1.218(2) . ?
O5 N2 1.231(2) . ?
O6 N3 1.224(2) . ?
O7 N3 1.222(2) . ?
N1 C2 1.343(2) . ?
N1 C2 1.343(2) 2_655 ?
N2 C8 1.473(2) . ?
N3 C10 1.472(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.502(3) . ?
C2 C3 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.517(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C8 C9 1.377(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?

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 141.18(7) . 2_655 ?
O2 Mn1 O1 82.49(5) 2_655 2_655 ?
O2 Mn1 O1 96.77(5) 2_655 . ?
O2 Mn1 O1 96.77(5) . 2_655 ?
O2 Mn1 O1 82.49(5) . . ?
O2 Mn1 O2 177.79(7) . 2_655 ?
O2 Mn1 O3 84.81(5) . 6 ?
O2 Mn1 O3 96.97(5) 2_655 6 ?
O2 Mn1 O3 96.98(5) . 5_656 ?
O2 Mn1 O3 84.81(5) 2_655 5_656 ?
O2 Mn1 N1 88.89(3) . . ?
O2 Mn1 N1 88.89(3) 2_655 . ?
O3 Mn1 O1 74.27(5) 6 2_655 ?
O3 Mn1 O1 143.48(5) 6 . ?
O3 Mn1 O1 74.27(5) 5_656 . ?
O3 Mn1 O1 143.48(5) 5_656 2_655 ?
O3 Mn1 O3 73.51(6) 6 5_656 ?
N1 Mn1 O1 70.59(3) . 2_655 ?
N1 Mn1 O1 70.59(3) . . ?
N1 Mn1 O3 143.25(3) . 5_656 ?
N1 Mn1 O3 143.25(3) . 6 ?
Mn1 O1 H1 111.6(12) . . ?
C1 O1 Mn1 119.44(11) . . ?
C1 O1 H1 102.5(12) . . ?
C5 O2 Mn1 131.58(12) . . ?
C5 O3 Mn1 135.52(11) . 5_656 ?
C2 N1 Mn1 120.56(11) 2_655 . ?
C2 N1 Mn1 120.56(11) . . ?
C2 N1 C2 118.9(2) . 2_655 ?
O4 N2 O5 124.39(16) . . ?
O4 N2 C8 117.87(16) . . ?
O5 N2 C8 117.73(16) . . ?
O6 N3 C10 117.02(15) . . ?
O7 N3 O6 124.38(17) . . ?
O7 N3 C10 118.58(16) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.59(15) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C2 C1 117.59(17) . . ?
N1 C2 C3 122.05(18) . . ?
C3 C2 C1 120.36(16) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.87(19) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C3 119.2(3) . 2_655 ?
C3 C4 H4 120.4 2_655 . ?
C3 C4 H4 120.4 . . ?
O2 C5 O3 126.12(18) . . ?
O2 C5 C6 116.92(17) . . ?
O3 C5 C6 116.94(17) . . ?
C7 C6 C5 120.23(17) . . ?
C7 C6 C11 120.22(17) . . ?
C11 C6 C5 119.52(17) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.52(18) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 N2 119.54(17) . . ?
C9 C8 N2 117.16(17) . . ?
C9 C8 C7 123.25(17) . . ?
C8 C9 H9 121.9 . . ?
C8 C9 C10 116.25(18) . . ?
C10 C9 H9 121.9 . . ?
C9 C10 N3 117.47(17) . . ?
C11 C10 N3 119.12(17) . . ?
C11 C10 C9 123.34(18) . . ?
C6 C11 H11 120.8 . . ?
C10 C11 C6 118.40(17) . . ?
C10 C11 H11 120.8 . . ?

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 C2 -5.44(19) . . . . ?
Mn1 O2 C5 O3 -8.7(3) . . . . ?
Mn1 O2 C5 C6 169.82(11) . . . . ?
Mn1 O3 C5 O2 -85.5(2) 5_656 . . . ?
Mn1 O3 C5 C6 95.97(19) 5_656 . . . ?
Mn1 N1 C2 C1 -1.38(18) . . . . ?
Mn1 N1 C2 C3 179.09(12) . . . . ?
O1 C1 C2 N1 4.4(2) . . . . ?
O1 C1 C2 C3 -176.09(16) . . . . ?
O2 C5 C6 C7 8.0(2) . . . . ?
O2 C5 C6 C11 -173.51(16) . . . . ?
O3 C5 C6 C7 -173.26(16) . . . . ?
O3 C5 C6 C11 5.2(2) . . . . ?
O4 N2 C8 C7 20.1(3) . . . . ?
O4 N2 C8 C9 -157.36(17) . . . . ?
O5 N2 C8 C7 -160.90(17) . . . . ?
O5 N2 C8 C9 21.7(2) . . . . ?
O6 N3 C10 C9 13.8(2) . . . . ?
O6 N3 C10 C11 -163.31(17) . . . . ?
O7 N3 C10 C9 -167.71(17) . . . . ?
O7 N3 C10 C11 15.2(3) . . . . ?
N1 C2 C3 C4 1.8(2) . . . . ?
N2 C8 C9 C10 176.49(17) . . . . ?
N3 C10 C11 C6 177.58(17) . . . . ?
C1 C2 C3 C4 -177.72(15) . . . . ?
C2 N1 C2 C1 178.62(18) 2_655 . . . ?
C2 N1 C2 C3 -0.91(12) 2_655 . . . ?
C2 C3 C4 C3 -0.85(12) . . . 2_655 ?
C5 C6 C7 C8 178.11(16) . . . . ?
C5 C6 C11 C10 -178.89(16) . . . . ?
C6 C7 C8 N2 -176.26(16) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 N3 -177.00(16) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C6 0.6(3) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1992057'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2022-02-19 deposited with the CCDC.	2022-10-20 downloaded from the CCDC.
;
_audit_creation_date             2022-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 Cl2 Mn N5 O14'
_chemical_formula_sum            'C21 H13 Cl2 Mn N5 O14'
_chemical_formula_weight         685.20
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.2964(3)
_cell_length_b                   14.6106(6)
_cell_length_c                   21.1398(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.033(3)
_cell_angle_gamma                90
_cell_volume                     2537.32(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24621
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.93
_cell_measurement_theta_min      3.69
_shelx_estimated_absorpt_T_max   0.515
_shelx_estimated_absorpt_T_min   0.214
_exptl_absorpt_coefficient_mu    6.952
_exptl_absorpt_correction_T_max  0.2381
_exptl_absorpt_correction_T_min  0.0073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26327
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.614
_diffrn_reflns_theta_min         3.689
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3676
_reflns_number_total             4826
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011  (Burla et al.,  2007)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.045
_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)+(0.0686P)²+0.4445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1125
_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) groups
2. Restrained distances
 O1-H1
 0.87 with sigma of 0.01
 O2-H2
 0.87 with sigma of 0.01
 C1-H1
 1.899993 with sigma of 0.02
 Mn1-H1
 2.947091 with sigma of 0.02
 C7-H2
 1.89644 with sigma of 0.02
 Mn1-H2
 2.940038 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C14(H14), C17(H17), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.24982(5) 0.57136(3) 0.50170(2) 0.02271(13) Uani 1 1 d D . . . .
Cl1 Cl 0.66351(10) 0.68649(5) 0.14894(3) 0.0423(2) Uani 1 1 d . . . . .
Cl2 Cl -0.15260(10) 0.64496(6) 0.86195(3) 0.0506(2) Uani 1 1 d . . . . .
O1 O 0.0034(2) 0.62831(12) 0.45357(8) 0.0265(4) Uani 1 1 d D . . . .
H1 H -0.0838(16) 0.6087(13) 0.4701(12) 0.040 Uiso 1 1 d D U . . .
O2 O 0.4962(2) 0.62070(13) 0.55379(8) 0.0280(4) Uani 1 1 d D . . . .
H2 H 0.5851(16) 0.6026(14) 0.5379(12) 0.042 Uiso 1 1 d D U . . .
O3 O 0.3678(2) 0.58069(12) 0.41747(8) 0.0262(4) Uani 1 1 d . . . . .
O4 O 0.6325(2) 0.56161(12) 0.45323(8) 0.0259(4) Uani 1 1 d . . . . .
O5 O 0.2200(2) 0.71673(14) 0.20285(9) 0.0354(5) Uani 1 1 d . . . . .
O6 O 0.3184(3) 0.63124(17) 0.13392(10) 0.0548(6) Uani 1 1 d . . . . .
O7 O 1.0160(2) 0.64792(16) 0.30437(10) 0.0417(5) Uani 1 1 d . . . . .
O8 O 0.9487(3) 0.58962(14) 0.21004(10) 0.0425(5) Uani 1 1 d . . . . .
O9 O 0.1369(2) 0.57135(12) 0.58746(8) 0.0259(4) Uani 1 1 d . . . . .
O10 O -0.1283(2) 0.55441(12) 0.55156(8) 0.0256(4) Uani 1 1 d . . . . .
O11 O 0.2850(2) 0.68717(14) 0.80988(9) 0.0376(5) Uani 1 1 d . . . . .
O12 O 0.1929(3) 0.58931(18) 0.87277(10) 0.0574(7) Uani 1 1 d . . . . .
O13 O -0.5084(2) 0.62068(16) 0.70504(10) 0.0437(5) Uani 1 1 d . . . . .
O14 O -0.4400(3) 0.55556(15) 0.79723(10) 0.0452(6) Uani 1 1 d . . . . .
N1 N 0.2522(2) 0.72903(16) 0.50568(9) 0.0262(5) Uani 1 1 d . . . . .
N2 N 0.3247(3) 0.66608(17) 0.18667(11) 0.0354(6) Uani 1 1 d . . . . .
N3 N 0.9162(3) 0.62112(16) 0.26026(11) 0.0330(5) Uani 1 1 d . . . . .
N4 N 0.1843(3) 0.63208(17) 0.82271(11) 0.0354(6) Uani 1 1 d . . . . .
N5 N -0.4081(3) 0.59136(17) 0.74798(12) 0.0349(6) Uani 1 1 d . . . . .
C1 C -0.0229(3) 0.72460(19) 0.44925(14) 0.0343(6) Uani 1 1 d D . . . .
H1A H -0.118230 0.740562 0.470471 0.041 Uiso 1 1 calc R U . . .
H1B H -0.047953 0.742205 0.403712 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1233(3) 0.77812(19) 0.47983(12) 0.0286(6) Uani 1 1 d . . . . .
C3 C 0.1226(4) 0.8729(2) 0.47991(13) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.029645 0.905990 0.461019 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2607(3) 0.9183(2) 0.50819(13) 0.0364(7) Uani 1 1 d . . . . .
H4 H 0.263648 0.983248 0.508952 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3942(4) 0.86833(19) 0.53527(13) 0.0333(6) Uani 1 1 d . . . . .
H5 H 0.489771 0.898313 0.554997 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3857(3) 0.77330(19) 0.53309(12) 0.0279(6) Uani 1 1 d . . . . .
C7 C 0.5250(3) 0.7158(2) 0.56402(14) 0.0339(6) Uani 1 1 d D . . . .
H7A H 0.625313 0.733318 0.546533 0.041 Uiso 1 1 calc R U . . .
H7B H 0.542803 0.728193 0.610510 0.041 Uiso 1 1 calc R U . . .
C8 C 0.5142(3) 0.57887(17) 0.41025(12) 0.0234(5) Uani 1 1 d . . . . .
C9 C 0.5531(3) 0.60149(18) 0.34411(12) 0.0246(5) Uani 1 1 d . . . . .
C10 C 0.4275(3) 0.62472(18) 0.29621(12) 0.0265(6) Uani 1 1 d . . . . .
H10 H 0.318168 0.626553 0.304801 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4638(3) 0.64524(19) 0.23557(12) 0.0295(6) Uani 1 1 d . . . . .
C12 C 0.6216(3) 0.64628(19) 0.22094(12) 0.0302(6) Uani 1 1 d . . . . .
C13 C 0.7438(3) 0.62263(18) 0.27038(12) 0.0279(6) Uani 1 1 d . . . . .
C14 C 0.7116(3) 0.60082(18) 0.33111(12) 0.0261(6) Uani 1 1 d . . . . .
H14 H 0.798253 0.585466 0.363683 0.031 Uiso 1 1 calc R U . . .
C15 C -0.0100(3) 0.56693(17) 0.59500(12) 0.0241(5) Uani 1 1 d . . . . .
C16 C -0.0461(3) 0.58134(17) 0.66269(12) 0.0241(5) Uani 1 1 d . . . . .
C17 C 0.0805(3) 0.60027(18) 0.71130(12) 0.0264(6) Uani 1 1 d . . . . .
H17 H 0.189562 0.603503 0.702563 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0450(3) 0.61436(18) 0.77276(12) 0.0290(6) Uani 1 1 d . . . . .
C19 C -0.1128(4) 0.6132(2) 0.78799(12) 0.0326(6) Uani 1 1 d . . . . .
C20 C -0.2356(3) 0.59438(19) 0.73756(13) 0.0302(6) Uani 1 1 d . . . . .
C21 C -0.2050(3) 0.57868(18) 0.67588(12) 0.0264(6) Uani 1 1 d . . . . .
H21 H -0.292123 0.566179 0.642827 0.032 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 O1 2.3079(18) . ?
Mn1 O2 2.2981(18) . ?
Mn1 O3 2.1530(17) . ?
Mn1 O4 2.3183(18) 3_666 ?
Mn1 O9 2.1540(17) . ?
Mn1 O10 2.3116(18) 3_566 ?
Mn1 N1 2.305(2) . ?
Cl1 C12 1.712(3) . ?
Cl2 C19 1.707(3) . ?
O1 H1 0.894(9) . ?
O1 C1 1.425(3) . ?
O2 H2 0.893(9) . ?
O2 C7 1.421(3) . ?
O3 C8 1.245(3) . ?
O4 C8 1.266(3) . ?
O5 N2 1.225(3) . ?
O6 N2 1.220(3) . ?
O7 N3 1.222(3) . ?
O8 N3 1.221(3) . ?
O9 C15 1.253(3) . ?
O10 C15 1.260(3) . ?
O11 N4 1.218(3) . ?
O12 N4 1.222(3) . ?
O13 N5 1.220(3) . ?
O14 N5 1.227(3) . ?
N1 C2 1.339(3) . ?
N1 C6 1.342(3) . ?
N2 C11 1.470(3) . ?
N3 C13 1.476(3) . ?
N4 C18 1.476(3) . ?
N5 C20 1.479(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.510(4) . ?
C2 C3 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(4) . ?
C6 C7 1.503(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(3) . ?
C9 C10 1.390(4) . ?
C9 C14 1.381(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.517(3) . ?
C16 C17 1.390(4) . ?
C16 C21 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?
C18 C19 1.391(4) . ?
C19 C20 1.395(4) . ?
C20 C21 1.382(4) . ?
C21 H21 0.9500 . ?

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 O4 141.21(6) . 3_666 ?
O1 Mn1 O10 76.87(6) . 3_566 ?
O2 Mn1 O1 140.53(7) . . ?
O2 Mn1 O4 76.75(6) . 3_666 ?
O2 Mn1 O10 141.34(6) . 3_566 ?
O2 Mn1 N1 70.52(7) . . ?
O3 Mn1 O1 95.15(6) . . ?
O3 Mn1 O2 84.24(6) . . ?
O3 Mn1 O4 100.31(7) . 3_666 ?
O3 Mn1 O9 176.15(7) . . ?
O3 Mn1 O10 82.26(6) . 3_566 ?
O3 Mn1 N1 87.96(7) . . ?
O9 Mn1 O1 84.73(6) . . ?
O9 Mn1 O2 93.39(7) . . ?
O9 Mn1 O4 82.05(6) . 3_666 ?
O9 Mn1 O10 101.45(7) . 3_566 ?
O9 Mn1 N1 88.39(7) . . ?
O10 Mn1 O4 70.36(7) 3_566 3_666 ?
N1 Mn1 O1 70.03(7) . . ?
N1 Mn1 O4 145.23(7) . 3_666 ?
N1 Mn1 O10 144.41(7) . 3_566 ?
Mn1 O1 H1 115.3(12) . . ?
C1 O1 Mn1 120.18(15) . . ?
C1 O1 H1 102.6(13) . . ?
Mn1 O2 H2 117.0(13) . . ?
C7 O2 Mn1 119.94(15) . . ?
C7 O2 H2 102.5(13) . . ?
C8 O3 Mn1 131.61(16) . . ?
C8 O4 Mn1 134.54(16) . 3_666 ?
C15 O9 Mn1 130.74(16) . . ?
C15 O10 Mn1 135.44(16) . 3_566 ?
C2 N1 Mn1 121.19(18) . . ?
C2 N1 C6 118.8(3) . . ?
C6 N1 Mn1 119.99(18) . . ?
O5 N2 C11 116.5(2) . . ?
O6 N2 O5 124.5(2) . . ?
O6 N2 C11 119.0(2) . . ?
O7 N3 C13 116.9(2) . . ?
O8 N3 O7 125.2(2) . . ?
O8 N3 C13 117.9(2) . . ?
O11 N4 O12 124.9(3) . . ?
O11 N4 C18 116.7(2) . . ?
O12 N4 C18 118.3(3) . . ?
O13 N5 O14 125.2(3) . . ?
O13 N5 C20 116.9(2) . . ?
O14 N5 C20 117.9(3) . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 C2 112.2(2) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N1 C2 C1 116.4(2) . . ?
N1 C2 C3 122.5(3) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(3) . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 122.0(3) . . ?
N1 C6 C7 117.2(2) . . ?
C5 C6 C7 120.8(2) . . ?
O2 C7 C6 112.2(2) . . ?
O2 C7 H7A 109.2 . . ?
O2 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O3 C8 O4 126.0(2) . . ?
O3 C8 C9 116.5(2) . . ?
O4 C8 C9 117.5(2) . . ?
C10 C9 C8 119.4(2) . . ?
C14 C9 C8 120.9(2) . . ?
C14 C9 C10 119.7(2) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 N2 116.3(2) . . ?
C12 C11 N2 120.9(2) . . ?
C12 C11 C10 122.8(2) . . ?
C11 C12 Cl1 121.1(2) . . ?
C11 C12 C13 116.1(2) . . ?
C13 C12 Cl1 122.4(2) . . ?
C12 C13 N3 120.9(2) . . ?
C14 C13 N3 116.6(2) . . ?
C14 C13 C12 122.6(2) . . ?
C9 C14 C13 119.7(2) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O9 C15 O10 126.0(2) . . ?
O9 C15 C16 115.9(2) . . ?
O10 C15 C16 118.1(2) . . ?
C17 C16 C15 119.8(2) . . ?
C21 C16 C15 120.3(2) . . ?
C21 C16 C17 119.9(2) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(2) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 N4 116.7(2) . . ?
C17 C18 C19 123.0(2) . . ?
C19 C18 N4 120.3(2) . . ?
C18 C19 Cl2 121.2(2) . . ?
C18 C19 C20 115.8(2) . . ?
C20 C19 Cl2 122.6(2) . . ?
C19 C20 N5 120.7(2) . . ?
C21 C20 N5 116.4(2) . . ?
C21 C20 C19 122.9(3) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 C16 119.4(2) . . ?
C20 C21 H21 120.3 . . ?

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 C2 -1.0(3) . . . . ?
Mn1 O2 C7 C6 -4.4(3) . . . . ?
Mn1 O3 C8 O4 7.4(4) . . . . ?
Mn1 O3 C8 C9 -171.21(16) . . . . ?
Mn1 O4 C8 O3 81.7(3) 3_666 . . . ?
Mn1 O4 C8 C9 -99.7(3) 3_666 . . . ?
Mn1 O9 C15 O10 5.6(4) . . . . ?
Mn1 O9 C15 C16 -172.20(16) . . . . ?
Mn1 O10 C15 O9 82.6(3) 3_566 . . . ?
Mn1 O10 C15 C16 -99.7(3) 3_566 . . . ?
Mn1 N1 C2 C1 0.9(3) . . . . ?
Mn1 N1 C2 C3 -178.19(19) . . . . ?
Mn1 N1 C6 C5 178.46(19) . . . . ?
Mn1 N1 C6 C7 -3.9(3) . . . . ?
Cl1 C12 C13 N3 -7.2(4) . . . . ?
Cl1 C12 C13 C14 171.9(2) . . . . ?
Cl2 C19 C20 N5 -6.7(4) . . . . ?
Cl2 C19 C20 C21 172.5(2) . . . . ?
O1 C1 C2 N1 0.1(3) . . . . ?
O1 C1 C2 C3 179.2(2) . . . . ?
O3 C8 C9 C10 1.5(4) . . . . ?
O3 C8 C9 C14 -179.6(2) . . . . ?
O4 C8 C9 C10 -177.2(2) . . . . ?
O4 C8 C9 C14 1.7(4) . . . . ?
O5 N2 C11 C10 43.9(3) . . . . ?
O5 N2 C11 C12 -136.2(3) . . . . ?
O6 N2 C11 C10 -134.6(3) . . . . ?
O6 N2 C11 C12 45.3(4) . . . . ?
O7 N3 C13 C12 142.2(3) . . . . ?
O7 N3 C13 C14 -36.9(3) . . . . ?
O8 N3 C13 C12 -41.0(4) . . . . ?
O8 N3 C13 C14 139.9(3) . . . . ?
O9 C15 C16 C17 1.5(4) . . . . ?
O9 C15 C16 C21 179.3(2) . . . . ?
O10 C15 C16 C17 -176.5(2) . . . . ?
O10 C15 C16 C21 1.4(4) . . . . ?
O11 N4 C18 C17 46.0(3) . . . . ?
O11 N4 C18 C19 -133.4(3) . . . . ?
O12 N4 C18 C17 -132.1(3) . . . . ?
O12 N4 C18 C19 48.5(4) . . . . ?
O13 N5 C20 C19 143.6(3) . . . . ?
O13 N5 C20 C21 -35.7(4) . . . . ?
O14 N5 C20 C19 -40.0(4) . . . . ?
O14 N5 C20 C21 140.6(3) . . . . ?
N1 C2 C3 C4 -0.3(4) . . . . ?
N1 C6 C7 O2 5.3(3) . . . . ?
N2 C11 C12 Cl1 8.9(4) . . . . ?
N2 C11 C12 C13 -178.0(2) . . . . ?
N3 C13 C14 C9 179.5(2) . . . . ?
N4 C18 C19 Cl2 7.6(4) . . . . ?
N4 C18 C19 C20 -179.0(2) . . . . ?
N5 C20 C21 C16 179.4(2) . . . . ?
C1 C2 C3 C4 -179.4(2) . . . . ?
C2 N1 C6 C5 -0.2(4) . . . . ?
C2 N1 C6 C7 177.4(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 N1 -0.1(4) . . . . ?
C4 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 O2 -177.1(2) . . . . ?
C6 N1 C2 C1 179.5(2) . . . . ?
C6 N1 C2 C3 0.4(4) . . . . ?
C8 C9 C10 C11 -179.9(2) . . . . ?
C8 C9 C14 C13 -179.4(2) . . . . ?
C9 C10 C11 N2 177.9(2) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 Cl1 -171.2(2) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C11 C12 C13 N3 179.8(2) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
C14 C9 C10 C11 1.2(4) . . . . ?
C15 C16 C17 C18 179.2(2) . . . . ?
C15 C16 C21 C20 -178.3(2) . . . . ?
C16 C17 C18 N4 178.6(2) . . . . ?
C16 C17 C18 C19 -2.0(4) . . . . ?
C17 C16 C21 C20 -0.4(4) . . . . ?
C17 C18 C19 Cl2 -171.7(2) . . . . ?
C17 C18 C19 C20 1.7(4) . . . . ?
C18 C19 C20 N5 -180.0(2) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C16 0.1(4) . . . . ?
C21 C16 C17 C18 1.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
