# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1882530'
_audit_update_record             
;
2019-02-12 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Co2 N16 O4'
_chemical_formula_sum            'C16 H16 Co2 N16 O4'
_chemical_formula_weight         614.31
_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'
Co Co 0.3494 0.9721 '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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   13.0625(7)
_cell_length_b                   26.5775(16)
_cell_length_c                   12.5503(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4357.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.828
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0735 before and 0.0483 after correction. The Ratio of minimum to maximum transmission is 0.9418. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.123
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            39444
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         2.377
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2617
_reflns_number_total             2704
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.319(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0195
_refine_ls_restrained_S_all      1.097
_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)+(0.0231P)²+6.8710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0462
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.681(14)
 0.319(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_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
Co1 Co 0.15998(2) 0.51349(2) 0.50532(3) 0.00776(8) Uani 1 1 d . . . . .
O1 O 0.18424(17) 0.51960(6) 0.67151(15) 0.0136(4) Uani 1 1 d . . . . .
H1A H 0.1951 0.5494 0.6884 0.020 Uiso 1 1 d R . . . .
H1B H 0.2339 0.5020 0.6915 0.020 Uiso 1 1 d R . . . .
O2 O 0.15925(13) 0.51022(6) 0.33243(16) 0.0108(5) Uani 1 1 d . . . . .
H2A H 0.1208 0.5330 0.3099 0.016 Uiso 1 1 d R . . . .
H2B H 0.1337 0.4827 0.3142 0.016 Uiso 1 1 d R . . . .
N1 N 0.27170(14) 0.45182(6) 0.5009(2) 0.0101(3) Uani 1 1 d . . . . .
N2 N 0.07269(13) 0.44964(6) 0.51423(18) 0.0083(4) Uani 1 1 d . . . . .
N3 N -0.02896(13) 0.44088(6) 0.5123(2) 0.0081(3) Uani 1 1 d . . . . .
N4 N 0.05081(14) 0.36656(6) 0.49498(19) 0.0084(4) Uani 1 1 d . . . . .
N5 N -0.21824(14) 0.41006(7) 0.49144(17) 0.0089(4) Uani 1 1 d . . . . .
N6 N -0.30757(14) 0.38546(7) 0.4995(2) 0.0104(4) Uani 1 1 d . . . . .
N7 N -0.28789(13) 0.33706(7) 0.5081(2) 0.0109(4) Uani 1 1 d . . . . .
N8 N -0.18525(13) 0.32862(6) 0.5070(2) 0.0106(3) Uani 1 1 d . . . . .
C1 C 0.37430(17) 0.45569(8) 0.4998(2) 0.0146(4) Uani 1 1 d . . . . .
H1 H 0.4039 0.4883 0.4984 0.017 Uiso 1 1 calc R . . . .
C2 C 0.43902(17) 0.41443(9) 0.5005(3) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.5112 0.4186 0.4994 0.018 Uiso 1 1 calc R . . . .
C3 C 0.39561(17) 0.36694(9) 0.5028(3) 0.0138(4) Uani 1 1 d . . . . .
H3 H 0.4381 0.3380 0.5040 0.017 Uiso 1 1 calc R . . . .
C4 C 0.28981(17) 0.36170(8) 0.5033(2) 0.0121(4) Uani 1 1 d . . . . .
H4 H 0.2591 0.3293 0.5042 0.014 Uiso 1 1 calc R . . . .
C5 C 0.23018(17) 0.40476(7) 0.5024(2) 0.0088(4) Uani 1 1 d . . . . .
C6 C 0.11826(16) 0.40510(7) 0.5037(2) 0.0078(4) Uani 1 1 d . . . . .
C7 C -0.03944(16) 0.39115(7) 0.5010(2) 0.0078(4) Uani 1 1 d . . . . .
C8 C -0.14535(16) 0.37433(7) 0.4967(2) 0.0084(4) 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
Co1 O1 2.116(2) . ?
Co1 O2 2.172(2) . ?
Co1 N1 2.1954(17) . ?
Co1 N2 2.0477(18) . ?
Co1 N3 2.0994(17) 2_565 ?
Co1 N5 2.1767(18) 2_565 ?
O1 H1A 0.8333 . ?
O1 H1B 0.8375 . ?
O2 H2A 0.8365 . ?
O2 H2B 0.8347 . ?
N1 C1 1.344(3) . ?
N1 C5 1.364(3) . ?
N2 N3 1.348(2) . ?
N2 C6 1.331(3) . ?
N3 Co1 2.0995(17) 2_565 ?
N3 C7 1.336(2) . ?
N4 C6 1.355(3) . ?
N4 C7 1.350(3) . ?
N5 Co1 2.1766(18) 2_565 ?
N5 N6 1.342(3) . ?
N5 C8 1.346(3) . ?
N6 N7 1.316(3) . ?
N7 N8 1.359(2) . ?
N8 C8 1.328(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 C6 1.462(3) . ?
C7 C8 1.455(3) . ?

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 Co1 O2 171.37(8) . . ?
O1 Co1 N1 89.02(8) . . ?
O1 Co1 N5 87.42(8) . 2_565 ?
O2 Co1 N1 86.99(8) . . ?
O2 Co1 N5 87.65(7) . 2_565 ?
N2 Co1 O1 95.34(8) . . ?
N2 Co1 O2 91.08(8) . . ?
N2 Co1 N1 75.68(7) . . ?
N2 Co1 N3 91.29(7) . 2_565 ?
N2 Co1 N5 166.59(7) . 2_565 ?
N3 Co1 O1 92.10(9) 2_565 . ?
N3 Co1 O2 93.51(8) 2_565 . ?
N3 Co1 N1 166.98(6) 2_565 . ?
N3 Co1 N5 75.47(7) 2_565 2_565 ?
N5 Co1 N1 117.55(7) 2_565 . ?
Co1 O1 H1A 110.4 . . ?
Co1 O1 H1B 111.6 . . ?
H1A O1 H1B 108.8 . . ?
Co1 O2 H2A 108.1 . . ?
Co1 O2 H2B 108.1 . . ?
H2A O2 H2B 107.6 . . ?
C1 N1 Co1 127.30(15) . . ?
C1 N1 C5 117.83(18) . . ?
C5 N1 Co1 114.84(13) . . ?
N3 N2 Co1 133.67(14) . . ?
C6 N2 Co1 118.85(14) . . ?
C6 N2 N3 106.56(17) . . ?
N2 N3 Co1 134.73(14) . 2_565 ?
C7 N3 Co1 118.91(15) . 2_565 ?
C7 N3 N2 105.88(17) . . ?
C7 N4 C6 101.38(16) . . ?
N6 N5 Co1 138.86(14) . 2_565 ?
N6 N5 C8 105.52(17) . . ?
C8 N5 Co1 114.03(14) . 2_565 ?
N7 N6 N5 108.22(17) . . ?
N6 N7 N8 110.67(17) . . ?
C8 N8 N7 103.72(17) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(2) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.3(2) . . ?
N1 C5 C6 113.09(17) . . ?
C4 C5 C6 124.6(2) . . ?
N2 C6 N4 112.90(18) . . ?
N2 C6 C5 116.99(18) . . ?
N4 C6 C5 130.11(18) . . ?
N3 C7 N4 113.28(18) . . ?
N3 C7 C8 113.90(18) . . ?
N4 C7 C8 132.82(18) . . ?
N5 C8 C7 117.23(18) . . ?
N8 C8 N5 111.87(18) . . ?
N8 C8 C7 130.59(19) . . ?

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
Co1 N1 C1 C2 177.8(2) . . . . ?
Co1 N1 C5 C4 -178.0(2) . . . . ?
Co1 N1 C5 C6 1.6(3) . . . . ?
Co1 N2 N3 Co1 -3.0(4) . . . 2_565 ?
Co1 N2 N3 C7 168.6(2) . . . . ?
Co1 N2 C6 N4 -170.61(18) . . . . ?
Co1 N2 C6 C5 8.9(3) . . . . ?
Co1 N3 C7 N4 173.00(18) 2_565 . . . ?
Co1 N3 C7 C8 -6.6(4) 2_565 . . . ?
Co1 N5 N6 N7 -164.4(2) 2_565 . . . ?
Co1 N5 C8 N8 168.8(2) 2_565 . . . ?
Co1 N5 C8 C7 -5.4(3) 2_565 . . . ?
N1 C1 C2 C3 -0.2(4) . . . . ?
N1 C5 C6 N2 -6.7(4) . . . . ?
N1 C5 C6 N4 172.8(3) . . . . ?
N2 N3 C7 N4 -0.2(3) . . . . ?
N2 N3 C7 C8 -179.8(2) . . . . ?
N3 N2 C6 N4 -0.1(3) . . . . ?
N3 N2 C6 C5 179.4(2) . . . . ?
N3 C7 C8 N5 7.9(4) . . . . ?
N3 C7 C8 N8 -165.1(3) . . . . ?
N4 C7 C8 N5 -171.6(3) . . . . ?
N4 C7 C8 N8 15.5(6) . . . . ?
N5 N6 N7 N8 0.7(4) . . . . ?
N6 N5 C8 N8 0.4(3) . . . . ?
N6 N5 C8 C7 -173.8(3) . . . . ?
N6 N7 N8 C8 -0.4(3) . . . . ?
N7 N8 C8 N5 0.0(3) . . . . ?
N7 N8 C8 C7 173.2(3) . . . . ?
C1 N1 C5 C4 0.3(5) . . . . ?
C1 N1 C5 C6 179.9(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 N1 0.1(4) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
C4 C5 C6 N2 172.9(3) . . . . ?
C4 C5 C6 N4 -7.6(5) . . . . ?
C5 N1 C1 C2 -0.2(4) . . . . ?
C6 N2 N3 Co1 -171.4(2) . . . 2_565 ?
C6 N2 N3 C7 0.2(3) . . . . ?
C6 N4 C7 N3 0.1(3) . . . . ?
C6 N4 C7 C8 179.6(4) . . . . ?
C7 N4 C6 N2 0.0(3) . . . . ?
C7 N4 C6 C5 -179.5(3) . . . . ?
C8 N5 N6 N7 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.681(14)
2 0.319(14)

####################################################################### 
# 
# 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 1882531'
_audit_update_record             
;
2019-02-12 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Mn2 N16 O4'
_chemical_formula_sum            'C16 H16 Mn2 N16 O4'
_chemical_formula_weight         606.33
_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'
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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   13.1899(8)
_cell_length_b                   27.1044(18)
_cell_length_c                   12.7668(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4564.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5060
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.224
_cell_measurement_theta_min      2.342
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    1.170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0504 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.9117. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.063
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9889
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.344
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2345
_reflns_number_total             2565
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+1.7244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_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 0.33069(3) 0.51330(2) 0.49482(5) 0.00901(12) Uani 1 1 d . . . . .
O1 O 0.30573(18) 0.52086(8) 0.32595(19) 0.0160(5) Uani 1 1 d . . . . .
H1A H 0.2948 0.5507 0.3091 0.019 Uiso 1 1 d R . . . .
H1B H 0.2560 0.5033 0.3060 0.019 Uiso 1 1 d R . . . .
O2 O 0.33980(15) 0.50945(8) 0.6719(2) 0.0115(6) Uani 1 1 d . . . . .
H2A H 0.3782 0.5323 0.6943 0.014 Uiso 1 1 d R . . . .
H2B H 0.3653 0.4820 0.6901 0.014 Uiso 1 1 d R . . . .
N1 N 0.22614(15) 0.44519(9) 0.4988(3) 0.0119(5) Uani 1 1 d . . . . .
N2 N 0.42777(15) 0.44830(8) 0.4859(2) 0.0094(5) Uani 1 1 d . . . . .
N3 N 0.52985(16) 0.44015(8) 0.4872(3) 0.0095(5) Uani 1 1 d . . . . .
N4 N 0.45273(16) 0.36677(8) 0.5049(3) 0.0099(5) Uani 1 1 d . . . . .
N5 N 0.72069(17) 0.40712(9) 0.5101(2) 0.0104(6) Uani 1 1 d . . . . .
N6 N 0.80730(16) 0.38106(9) 0.5014(3) 0.0119(5) Uani 1 1 d . . . . .
N7 N 0.78385(16) 0.33426(9) 0.4905(3) 0.0119(5) Uani 1 1 d . . . . .
N8 N 0.68137(16) 0.32821(8) 0.4906(3) 0.0114(5) Uani 1 1 d . . . . .
C1 C 0.1237(2) 0.44527(11) 0.4987(4) 0.0169(6) Uani 1 1 d . . . . .
H1 H 0.0896 0.4761 0.4993 0.020 Uiso 1 1 calc R . . . .
C2 C 0.0660(2) 0.40276(13) 0.4978(4) 0.0189(7) Uani 1 1 d . . . . .
H2 H -0.0059 0.4043 0.4976 0.023 Uiso 1 1 calc R . . . .
C3 C 0.1155(2) 0.35793(11) 0.4971(4) 0.0160(6) Uani 1 1 d . . . . .
H3 H 0.0777 0.3281 0.4966 0.019 Uiso 1 1 calc R . . . .
C4 C 0.2208(2) 0.35652(11) 0.4972(3) 0.0137(6) Uani 1 1 d . . . . .
H4 H 0.2560 0.3259 0.4969 0.016 Uiso 1 1 calc R . . . .
C5 C 0.2733(2) 0.40088(10) 0.4976(3) 0.0096(6) Uani 1 1 d . . . . .
C6 C 0.38507(19) 0.40396(9) 0.4966(3) 0.0085(5) Uani 1 1 d . . . . .
C7 C 0.54125(19) 0.39160(9) 0.4988(3) 0.0085(6) Uani 1 1 d . . . . .
C8 C 0.64549(19) 0.37382(10) 0.5027(3) 0.0094(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 O1 2.191(2) . ?
Mn1 O2 2.267(3) . ?
Mn1 N1 2.305(2) . ?
Mn1 N2 2.181(2) . ?
Mn1 N3 2.233(2) 2_665 ?
Mn1 N5 2.269(2) 2_665 ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.8502 . ?
O2 H2B 0.8497 . ?
N1 C1 1.352(3) . ?
N1 C5 1.353(4) . ?
N2 N3 1.364(3) . ?
N2 C6 1.334(3) . ?
N3 Mn1 2.233(2) 2_665 ?
N3 C7 1.333(3) . ?
N4 C6 1.351(3) . ?
N4 C7 1.350(3) . ?
N5 Mn1 2.269(2) 2_665 ?
N5 N6 1.348(3) . ?
N5 C8 1.344(3) . ?
N6 N7 1.313(3) . ?
N7 N8 1.362(3) . ?
N8 C8 1.333(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 C6 1.477(3) . ?
C7 C8 1.458(3) . ?

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 O2 173.75(10) . . ?
O1 Mn1 N1 90.40(11) . . ?
O1 Mn1 N3 91.62(10) . 2_665 ?
O1 Mn1 N5 87.17(9) . 2_665 ?
O2 Mn1 N1 88.43(10) . . ?
O2 Mn1 N5 88.51(9) . 2_665 ?
N2 Mn1 O1 96.46(10) . . ?
N2 Mn1 O2 89.06(10) . . ?
N2 Mn1 N1 72.87(7) . . ?
N2 Mn1 N3 88.31(8) . 2_665 ?
N2 Mn1 N5 161.37(8) . 2_665 ?
N3 Mn1 O2 91.47(10) 2_665 . ?
N3 Mn1 N1 161.18(8) 2_665 . ?
N3 Mn1 N5 73.30(8) 2_665 2_665 ?
N5 Mn1 N1 125.50(8) 2_665 . ?
Mn1 O1 H1A 111.3 . . ?
Mn1 O1 H1B 111.0 . . ?
H1A O1 H1B 109.2 . . ?
Mn1 O2 H2A 109.5 . . ?
Mn1 O2 H2B 109.5 . . ?
H2A O2 H2B 108.1 . . ?
C1 N1 Mn1 126.7(2) . . ?
C1 N1 C5 117.5(2) . . ?
C5 N1 Mn1 115.83(16) . . ?
N3 N2 Mn1 135.19(17) . . ?
C6 N2 Mn1 118.32(16) . . ?
C6 N2 N3 105.6(2) . . ?
N2 N3 Mn1 136.22(17) . 2_665 ?
C7 N3 Mn1 117.40(17) . 2_665 ?
C7 N3 N2 105.8(2) . . ?
C7 N4 C6 101.2(2) . . ?
N6 N5 Mn1 138.10(18) . 2_665 ?
C8 N5 Mn1 114.32(17) . 2_665 ?
C8 N5 N6 105.5(2) . . ?
N7 N6 N5 108.4(2) . . ?
N6 N7 N8 110.5(2) . . ?
C8 N8 N7 103.9(2) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.3(3) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.7(2) . . ?
N1 C5 C6 114.1(2) . . ?
C4 C5 C6 123.2(3) . . ?
N2 C6 N4 113.7(2) . . ?
N2 C6 C5 118.2(2) . . ?
N4 C6 C5 128.1(2) . . ?
N3 C7 N4 113.7(2) . . ?
N3 C7 C8 115.9(2) . . ?
N4 C7 C8 130.5(2) . . ?
N5 C8 C7 118.4(2) . . ?
N8 C8 N5 111.6(2) . . ?
N8 C8 C7 129.6(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_4
_database_code_depnum_ccdc_archive 'CCDC 1882533'
_audit_update_record             
;
2019-02-12 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 Cu N8'
_chemical_formula_sum            'C8 H4 Cu N8'
_chemical_formula_weight         275.73
_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'
Cu Cu 0.3201 1.2651 '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'

_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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   13.0946(10)
_cell_length_b                   13.0946(10)
_cell_length_c                   11.3554(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1947.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4681
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    2.232
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1172 before and 0.0885 after correction. The Ratio of minimum to maximum transmission is 0.6542. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15666
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.999
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.374
_diffrn_ambient_temperature      120.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1707
_reflns_number_total             1911
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(14)
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0289
_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)+(0.0108P)²+1.3881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 0.49634(4) 0.70598(4) 0.54386(4) 0.00896(16) Uani 1 1 d . . . . .
N1 N 0.4426(3) 0.7343(3) 0.7112(3) 0.0108(8) Uani 1 1 d . . . . .
N2 N 0.5687(3) 0.6035(3) 0.6335(3) 0.0107(8) Uani 1 1 d . . . . .
N3 N 0.6414(3) 0.5365(3) 0.6055(3) 0.0100(8) Uani 1 1 d . . . . .
N4 N 0.6318(3) 0.5416(3) 0.8032(3) 0.0102(8) Uani 1 1 d . . . . .
N5 N 0.7808(3) 0.4078(3) 0.5720(3) 0.0128(8) Uani 1 1 d . . . . .
N6 N 0.8573(3) 0.3416(3) 0.5707(3) 0.0142(8) Uani 1 1 d . . . . .
N7 N 0.8812(3) 0.3210(3) 0.6816(3) 0.0152(8) Uani 1 1 d . . . . .
N8 N 0.8200(3) 0.3733(3) 0.7572(3) 0.0126(8) Uani 1 1 d . . . . .
C1 C 0.3761(4) 0.8059(4) 0.7415(4) 0.0164(10) Uani 1 1 d . . . . .
H1 H 0.3435 0.8441 0.6811 0.020 Uiso 1 1 calc R . . . .
C2 C 0.3519(4) 0.8275(4) 0.8585(4) 0.0222(12) Uani 1 1 d . . . . .
H2 H 0.3036 0.8789 0.8777 0.027 Uiso 1 1 calc R . . . .
C3 C 0.4004(4) 0.7718(4) 0.9460(4) 0.0204(11) Uani 1 1 d . . . . .
H3 H 0.3857 0.7851 1.0265 0.024 Uiso 1 1 calc R . . . .
C4 C 0.4709(3) 0.6963(3) 0.9157(3) 0.0125(9) Uani 1 1 d . . . . .
H4 H 0.5043 0.6572 0.9747 0.015 Uiso 1 1 calc R . . . .
C5 C 0.4909(3) 0.6796(3) 0.7978(3) 0.0102(9) Uani 1 1 d . . . . .
C6 C 0.5642(3) 0.6062(3) 0.7508(4) 0.0096(10) Uani 1 1 d . . . . .
C7 C 0.6779(3) 0.5005(3) 0.7071(3) 0.0110(9) Uani 1 1 d . . . . .
C8 C 0.7596(3) 0.4260(3) 0.6868(4) 0.0115(9) 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
Cu1 N1 2.060(3) . ?
Cu1 N2 1.933(4) . ?
Cu1 N3 1.967(3) 7_556 ?
Cu1 N5 2.009(4) 7_556 ?
Cu1 N7 2.217(4) 5_656 ?
N1 C1 1.326(5) . ?
N1 C5 1.371(5) . ?
N2 N3 1.334(5) . ?
N2 C6 1.333(5) . ?
N3 Cu1 1.967(3) 7_556 ?
N3 C7 1.335(5) . ?
N4 C6 1.362(5) . ?
N4 C7 1.358(5) . ?
N5 Cu1 2.009(4) 7_556 ?
N5 N6 1.325(5) . ?
N5 C8 1.354(5) . ?
N6 N7 1.326(5) . ?
N7 Cu1 2.217(3) 5_646 ?
N7 N8 1.360(5) . ?
N8 C8 1.320(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(5) . ?
C5 C6 1.459(6) . ?
C7 C8 1.466(6) . ?

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
N1 Cu1 N7 90.51(13) . 5_656 ?
N2 Cu1 N1 78.84(14) . . ?
N2 Cu1 N3 91.43(14) . 7_556 ?
N2 Cu1 N5 165.16(15) . 7_556 ?
N2 Cu1 N7 92.92(15) . 5_656 ?
N3 Cu1 N1 164.62(15) 7_556 . ?
N3 Cu1 N5 78.42(14) 7_556 7_556 ?
N3 Cu1 N7 101.95(15) 7_556 5_656 ?
N5 Cu1 N1 108.60(14) 7_556 . ?
N5 Cu1 N7 99.71(15) 7_556 5_656 ?
C1 N1 Cu1 126.3(3) . . ?
C1 N1 C5 119.1(4) . . ?
C5 N1 Cu1 114.2(3) . . ?
N3 N2 Cu1 132.9(3) . . ?
C6 N2 Cu1 119.1(3) . . ?
C6 N2 N3 106.7(4) . . ?
N2 N3 Cu1 133.5(3) . 7_556 ?
N2 N3 C7 106.3(3) . . ?
C7 N3 Cu1 119.8(3) . 7_556 ?
C7 N4 C6 100.6(3) . . ?
N6 N5 Cu1 137.6(3) . 7_556 ?
N6 N5 C8 106.3(3) . . ?
C8 N5 Cu1 115.4(3) . 7_556 ?
N5 N6 N7 107.5(3) . . ?
N6 N7 Cu1 115.4(3) . 5_646 ?
N6 N7 N8 111.0(3) . . ?
N8 N7 Cu1 133.6(3) . 5_646 ?
C8 N8 N7 103.6(3) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(4) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.3(4) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 C6 112.7(4) . . ?
C4 C5 C6 125.7(4) . . ?
N2 C6 N4 113.0(4) . . ?
N2 C6 C5 114.3(4) . . ?
N4 C6 C5 132.6(4) . . ?
N3 C7 N4 113.3(4) . . ?
N3 C7 C8 111.1(3) . . ?
N4 C7 C8 135.6(4) . . ?
N5 C8 C7 114.7(4) . . ?
N8 C8 N5 111.6(4) . . ?
N8 C8 C7 133.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C2 -172.8(4) . . . . ?
Cu1 N1 C5 C4 173.9(3) . . . . ?
Cu1 N1 C5 C6 -5.1(4) . . . . ?
Cu1 N2 N3 Cu1 -6.6(6) . . . 7_556 ?
Cu1 N2 N3 C7 166.9(3) . . . . ?
Cu1 N2 C6 N4 -169.3(3) . . . . ?
Cu1 N2 C6 C5 8.7(5) . . . . ?
Cu1 N3 C7 N4 174.5(3) 7_556 . . . ?
Cu1 N3 C7 C8 -5.0(5) 7_556 . . . ?
Cu1 N5 N6 N7 169.9(4) 7_556 . . . ?
Cu1 N5 C8 N8 -172.8(3) 7_556 . . . ?
Cu1 N5 C8 C7 5.9(5) 7_556 . . . ?
Cu1 N7 N8 C8 -176.8(4) 5_646 . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
N1 C5 C6 N2 -1.8(5) . . . . ?
N1 C5 C6 N4 175.7(4) . . . . ?
N2 N3 C7 N4 -0.1(5) . . . . ?
N2 N3 C7 C8 -179.6(3) . . . . ?
N3 N2 C6 N4 -0.6(5) . . . . ?
N3 N2 C6 C5 177.4(3) . . . . ?
N3 C7 C8 N5 -0.8(6) . . . . ?
N3 C7 C8 N8 177.4(5) . . . . ?
N4 C7 C8 N5 179.9(5) . . . . ?
N4 C7 C8 N8 -1.9(9) . . . . ?
N5 N6 N7 Cu1 177.4(3) . . . 5_646 ?
N5 N6 N7 N8 0.3(6) . . . . ?
N6 N5 C8 N8 -0.2(6) . . . . ?
N6 N5 C8 C7 178.4(4) . . . . ?
N6 N7 N8 C8 -0.5(5) . . . . ?
N7 N8 C8 N5 0.4(5) . . . . ?
N7 N8 C8 C7 -177.9(5) . . . . ?
C1 N1 C5 C4 1.0(6) . . . . ?
C1 N1 C5 C6 -178.1(4) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C2 C3 C4 C5 0.4(7) . . . . ?
C3 C4 C5 N1 -0.8(6) . . . . ?
C3 C4 C5 C6 178.1(4) . . . . ?
C4 C5 C6 N2 179.2(4) . . . . ?
C4 C5 C6 N4 -3.3(8) . . . . ?
C5 N1 C1 C2 -0.8(7) . . . . ?
C6 N2 N3 Cu1 -173.1(3) . . . 7_556 ?
C6 N2 N3 C7 0.4(4) . . . . ?
C6 N4 C7 N3 -0.2(5) . . . . ?
C6 N4 C7 C8 179.1(5) . . . . ?
C7 N4 C6 N2 0.5(5) . . . . ?
C7 N4 C6 C5 -177.1(5) . . . . ?
C8 N5 N6 N7 -0.1(5) . . . . ?

_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_3
_database_code_depnum_ccdc_archive 'CCDC 1882532'
_audit_update_record             
;
2019-02-12 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 Mn N8 O2'
_chemical_formula_sum            'C8 H8 Mn N8 O2'
_chemical_formula_weight         303.16
_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'
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      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                   14.6205(14)
_cell_length_b                   12.1534(12)
_cell_length_c                   6.2740(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1114.82(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0951 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.9638. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            29156
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_min         3.252
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2686
_reflns_number_total             2782
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0190
_refine_ls_restrained_S_all      1.104
_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)+(0.0269P)²+0.2052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0477
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
;
_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 0.58203(2) 0.60798(2) 0.23183(6) 0.00912(8) Uani 1 1 d . . . . .
O1 O 0.65121(10) 0.74717(11) 0.4064(2) 0.0137(3) Uani 1 1 d . . . . .
H1A H 0.6684 0.7959 0.3178 0.021 Uiso 1 1 d R . . . .
H1B H 0.6983 0.7230 0.4707 0.021 Uiso 1 1 d R . . . .
O2 O 0.67320(10) 0.63795(12) -0.0278(3) 0.0153(3) Uani 1 1 d . . . . .
H2A H 0.697(2) 0.691(2) -0.031(5) 0.023 Uiso 1 1 d R . . . .
H2B H 0.691(2) 0.598(2) -0.131(5) 0.023 Uiso 1 1 d R . . . .
N1 N 0.49202(11) 0.74785(14) 0.0854(3) 0.0130(3) Uani 1 1 d . . . . .
N2 N 0.45887(11) 0.61701(13) 0.4255(3) 0.0101(3) Uani 1 1 d . . . . .
N3 N 0.42463(10) 0.56509(13) 0.6000(3) 0.0099(3) Uani 1 1 d . . . . .
N4 N 0.34043(11) 0.71839(13) 0.5448(3) 0.0115(3) Uani 1 1 d . . . . .
N5 N 0.32583(11) 0.49862(13) 0.9476(3) 0.0111(3) Uani 1 1 d . . . . .
N6 N 0.27324(11) 0.49515(13) 1.1239(3) 0.0129(3) Uani 1 1 d . . . . .
N7 N 0.22399(12) 0.58557(14) 1.1336(3) 0.0146(3) Uani 1 1 d . . . . .
N8 N 0.24359(11) 0.65103(13) 0.9656(3) 0.0137(3) Uani 1 1 d . . . . .
C1 C 0.50696(14) 0.80780(18) -0.0898(3) 0.0170(4) Uani 1 1 d . . . . .
H1 H 0.5533 0.7847 -0.1862 0.020 Uiso 1 1 calc R . . . .
C2 C 0.45737(16) 0.90284(18) -0.1371(4) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.4688 0.9425 -0.2648 0.024 Uiso 1 1 calc R . . . .
C3 C 0.39158(15) 0.93815(17) 0.0047(4) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.3580 1.0035 -0.0226 0.023 Uiso 1 1 calc R . . . .
C4 C 0.37493(14) 0.87705(16) 0.1880(3) 0.0160(5) Uani 1 1 d . . . . .
H4 H 0.3305 0.9002 0.2890 0.019 Uiso 1 1 calc R . . . .
C5 C 0.42486(11) 0.78131(14) 0.2194(4) 0.0110(3) Uani 1 1 d . . . . .
C6 C 0.40751(12) 0.70703(15) 0.3988(3) 0.0101(3) Uani 1 1 d . . . . .
C7 C 0.35477(13) 0.62839(15) 0.6649(3) 0.0098(3) Uani 1 1 d . . . . .
C8 C 0.30609(13) 0.59512(15) 0.8563(3) 0.0101(4) 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 O1 2.2550(14) . ?
Mn1 O2 2.1361(15) . ?
Mn1 N1 2.3378(17) . ?
Mn1 N2 2.1750(16) . ?
Mn1 N3 2.2623(16) 2_664 ?
Mn1 N5 2.3077(16) 2_664 ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.74(3) . ?
O2 H2B 0.85(3) . ?
N1 C1 1.337(3) . ?
N1 C5 1.355(3) . ?
N2 N3 1.359(2) . ?
N2 C6 1.338(2) . ?
N3 Mn1 2.2622(16) 2_665 ?
N3 C7 1.342(2) . ?
N4 C6 1.349(2) . ?
N4 C7 1.345(2) . ?
N5 Mn1 2.3077(16) 2_665 ?
N5 N6 1.348(2) . ?
N5 C8 1.337(2) . ?
N6 N7 1.315(2) . ?
N7 N8 1.351(2) . ?
N8 C8 1.329(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.465(3) . ?
C7 C8 1.453(3) . ?

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 N1 84.13(5) . . ?
O1 Mn1 N3 153.43(5) . 2_664 ?
O1 Mn1 N5 82.78(5) . 2_664 ?
O2 Mn1 O1 87.85(6) . . ?
O2 Mn1 N1 85.85(6) . . ?
O2 Mn1 N2 159.07(6) . . ?
O2 Mn1 N3 84.64(6) . 2_664 ?
O2 Mn1 N5 100.30(6) . 2_664 ?
N2 Mn1 O1 93.56(6) . . ?
N2 Mn1 N1 73.55(6) . . ?
N2 Mn1 N3 102.45(6) . 2_664 ?
N2 Mn1 N5 100.60(6) . 2_664 ?
N3 Mn1 N1 120.55(6) 2_664 . ?
N3 Mn1 N5 73.59(6) 2_664 2_664 ?
N5 Mn1 N1 165.30(6) 2_664 . ?
Mn1 O1 H1A 109.7 . . ?
Mn1 O1 H1B 109.5 . . ?
H1A O1 H1B 108.2 . . ?
Mn1 O2 H2A 118(2) . . ?
Mn1 O2 H2B 132.1(19) . . ?
H2A O2 H2B 110(3) . . ?
C1 N1 Mn1 128.87(14) . . ?
C1 N1 C5 117.71(18) . . ?
C5 N1 Mn1 112.48(13) . . ?
N3 N2 Mn1 137.01(12) . . ?
C6 N2 Mn1 115.86(12) . . ?
C6 N2 N3 105.89(15) . . ?
N2 N3 Mn1 137.89(12) . 2_665 ?
C7 N3 Mn1 112.91(12) . 2_665 ?
C7 N3 N2 104.99(15) . . ?
C7 N4 C6 100.60(15) . . ?
N6 N5 Mn1 142.83(12) . 2_665 ?
C8 N5 Mn1 111.55(12) . 2_665 ?
C8 N5 N6 104.83(15) . . ?
N7 N6 N5 108.90(15) . . ?
N6 N7 N8 109.88(16) . . ?
C8 N8 N7 104.32(15) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(2) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.89(19) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.31(19) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 C6 114.65(15) . . ?
C4 C5 C6 122.33(19) . . ?
N2 C6 N4 114.00(17) . . ?
N2 C6 C5 120.21(16) . . ?
N4 C6 C5 125.76(16) . . ?
N3 C7 N4 114.51(17) . . ?
N3 C7 C8 117.64(16) . . ?
N4 C7 C8 127.81(17) . . ?
N5 C8 C7 119.50(17) . . ?
N8 C8 N5 112.07(17) . . ?
N8 C8 C7 128.37(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
