# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2375107'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  O8       ..O5X      .       2.13 Ang.  
RESPONSE: Due to disorder.
;
_vrf_PLAT213_1                   
;
PROBLEM: Atom C9X             has ADP max/min Ratio .....        4.1 prolat
RESPONSE: Disordered atom. Some ADP restrains have been applied.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 Co2 N2 O8'
_chemical_formula_sum            'C20 H22 Co2 N2 O8'
_chemical_formula_weight         536.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.7720(4)
_cell_length_b                   12.6914(2)
_cell_length_c                   18.7308(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3987.04(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    34638
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            'intense blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.718
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   'SADABS v2007/2, Sheldrick, G.M., (2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_reflns_number            32878
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4572
_reflns_number_gt                3918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+39.6212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4572
_refine_ls_number_parameters     348
_refine_ls_number_restraints     369
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.26882(4) 0.22113(5) 0.36948(3) 0.01337(18) Uani 1 1 d D . . . .
Co2 Co 0.26733(4) 0.47752(5) 0.35863(3) 0.01406(19) Uani 1 1 d D . . . .
O1 O 0.3694(2) 0.4400(3) 0.3124(2) 0.0224(8) Uani 1 1 d . . . . .
O2 O 0.3782(2) 0.2679(3) 0.3360(2) 0.0195(8) Uani 1 1 d . . . . .
C1 C 0.4046(3) 0.3518(4) 0.3097(3) 0.0154(9) Uani 1 1 d . . . . .
C2 C 0.4828(3) 0.3494(4) 0.2724(3) 0.0172(10) Uani 1 1 d . . . . .
C3 C 0.5147(3) 0.4409(4) 0.2435(3) 0.0218(11) Uani 1 1 d . . . . .
H3 H 0.486254 0.505211 0.248219 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5872(3) 0.4405(4) 0.2078(3) 0.0208(11) Uani 1 1 d . . . . .
H4 H 0.607093 0.503907 0.187485 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6316(3) 0.3466(4) 0.2015(3) 0.0159(9) Uani 1 1 d . . . . .
C6 C 0.5993(3) 0.2549(4) 0.2314(3) 0.0214(11) Uani 1 1 d . . . . .
H6 H 0.627948 0.190481 0.228105 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5267(3) 0.2570(4) 0.2654(3) 0.0241(12) Uani 1 1 d . . . . .
H7 H 0.505866 0.193473 0.284680 0.029 Uiso 1 1 calc R U . . .
O3 O 0.7038(2) 0.3479(3) 0.16959(19) 0.0171(7) Uani 1 1 d . . . . .
O4 O 0.2773(7) 0.2703(6) 0.4720(3) 0.0232(17) Uani 0.736(15) 1 d D U P A 1
O5 O 0.2962(4) 0.4441(5) 0.4612(3) 0.0219(15) Uani 0.736(15) 1 d D U P A 1
C8 C 0.2878(6) 0.3630(7) 0.4972(4) 0.0211(17) Uani 0.736(15) 1 d D U P A 1
C9 C 0.2849(6) 0.3744(6) 0.5761(4) 0.0215(18) Uani 0.736(15) 1 d D U P A 1
C10 C 0.2798(6) 0.4728(6) 0.6092(4) 0.0203(16) Uani 0.736(15) 1 d D U P A 1
H10 H 0.280719 0.534529 0.580550 0.024 Uiso 0.736(15) 1 calc R U P A 1
C11 C 0.2735(6) 0.4829(6) 0.6829(4) 0.0194(17) Uani 0.736(15) 1 d D U P A 1
H11 H 0.272157 0.550878 0.704028 0.023 Uiso 0.736(15) 1 calc R U P A 1
C12 C 0.2689(3) 0.3923(4) 0.7262(3) 0.0215(10) Uani 1 1 d D U . . .
C13 C 0.2783(3) 0.2939(4) 0.6922(3) 0.0226(10) Uani 1 1 d D U . . .
H13 H 0.282348 0.231824 0.720297 0.027 Uiso 1 1 calc R U . . .
C14 C 0.2818(4) 0.2862(5) 0.6189(3) 0.0264(11) Uani 1 1 d D U . . .
H14 H 0.282013 0.218411 0.597338 0.032 Uiso 0.736(15) 1 calc R U P A 1
H14X H 0.296608 0.221728 0.596762 0.032 Uiso 0.264(15) 1 calc R U P A 2
O4X O 0.2868(19) 0.2959(18) 0.4638(9) 0.026(4) Uani 0.264(15) 1 d D U P A 2
O5X O 0.2519(14) 0.4645(13) 0.4625(6) 0.028(3) Uani 0.264(15) 1 d D U P A 2
C8X C 0.265(2) 0.3799(16) 0.4963(9) 0.025(3) Uani 0.264(15) 1 d D U P A 2
C9X C 0.263(2) 0.3766(13) 0.5766(8) 0.023(3) Uani 0.264(15) 1 d D U P A 2
C10X C 0.2438(18) 0.4736(14) 0.6099(9) 0.026(3) Uani 0.264(15) 1 d D U P A 2
H10X H 0.230448 0.533396 0.581856 0.031 Uiso 0.264(15) 1 calc R U P A 2
C11X C 0.2450(17) 0.4806(14) 0.6842(10) 0.021(4) Uani 0.264(15) 1 d D U P A 2
H11X H 0.229856 0.544406 0.706893 0.025 Uiso 0.264(15) 1 calc R U P A 2
O6 O 0.2619(2) 0.3982(3) 0.79665(18) 0.0173(7) Uani 1 1 d . . . . .
O7 O 0.1624(2) 0.1408(3) 0.4036(2) 0.0246(8) Uani 1 1 d . . . . .
C15 C 0.1283(4) 0.1469(5) 0.4616(3) 0.0341(14) Uani 1 1 d . . . . .
H15 H 0.160119 0.158533 0.502845 0.041 Uiso 1 1 calc R U . . .
N1 N 0.0503(4) 0.1383(5) 0.4704(4) 0.0504(17) Uani 1 1 d . . . . .
C16 C -0.0017(5) 0.1235(9) 0.4085(6) 0.073(3) Uani 1 1 d . . . . .
H16A H -0.024593 0.191424 0.394439 0.109 Uiso 1 1 calc R U . . .
H16B H -0.044766 0.074510 0.420860 0.109 Uiso 1 1 calc R U . . .
H16C H 0.029312 0.094535 0.368746 0.109 Uiso 1 1 calc R U . . .
C17 C 0.0135(7) 0.1511(9) 0.5406(6) 0.092(4) Uani 1 1 d . . . . .
H17A H 0.055099 0.161386 0.576620 0.138 Uiso 1 1 calc R U . . .
H17B H -0.017487 0.087876 0.552238 0.138 Uiso 1 1 calc R U . . .
H17C H -0.021899 0.212522 0.539935 0.138 Uiso 1 1 calc R U . . .
O8 O 0.1695(3) 0.5765(4) 0.4203(3) 0.0417(11) Uani 1 1 d . . . . .
C18 C 0.1370(5) 0.5802(8) 0.4802(5) 0.055(2) Uani 1 1 d . . . . .
H18 H 0.137050 0.647200 0.502757 0.066 Uiso 1 1 calc R U . . .
N2 N 0.1027(6) 0.5037(7) 0.5161(5) 0.075(3) Uani 1 1 d . . . . .
C19 C 0.0989(7) 0.3966(8) 0.4877(6) 0.071(3) Uani 1 1 d . . . . .
H19A H 0.129724 0.392658 0.443341 0.106 Uiso 1 1 calc R U . . .
H19B H 0.043241 0.378000 0.478044 0.106 Uiso 1 1 calc R U . . .
H19C H 0.121206 0.347354 0.522709 0.106 Uiso 1 1 calc R U . . .
C20 C 0.0733(8) 0.5181(10) 0.5892(6) 0.097(4) Uani 1 1 d . . . . .
H20A H 0.072801 0.593315 0.600906 0.145 Uiso 1 1 calc R U . . .
H20B H 0.108399 0.480759 0.622527 0.145 Uiso 1 1 calc R U . . .
H20C H 0.019147 0.489710 0.592930 0.145 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
Co1 O4 2.025(6) . ?
Co1 O4X 2.028(13) . ?
Co1 O2 2.028(3) . ?
Co1 O6 2.042(4) 7_565 ?
Co1 O3 2.077(3) 6_556 ?
Co1 O7 2.152(4) . ?
Co1 O8 2.313(5) 8_655 ?
Co1 Co2 3.2603(9) . ?
Co2 O5X 1.969(11) . ?
Co2 O1 1.977(4) . ?
Co2 O6 2.019(4) 2_564 ?
Co2 O5 2.025(5) . ?
Co2 O3 2.031(4) 6_556 ?
Co2 O8 2.367(5) . ?
O1 C1 1.266(6) . ?
O2 C1 1.254(6) . ?
C1 C2 1.487(7) . ?
C2 C3 1.389(7) . ?
C2 C7 1.390(7) . ?
C3 C4 1.388(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(7) . ?
C4 H4 0.9500 . ?
C5 O3 1.349(6) . ?
C5 C6 1.401(7) . ?
C6 C7 1.375(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
O4 C8 1.279(10) . ?
O5 C8 1.239(9) . ?
C8 C9 1.486(9) . ?
C9 C14 1.378(10) . ?
C9 C10 1.397(10) . ?
C10 C11 1.390(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(9) . ?
C11 H11 0.9500 . ?
C12 O6 1.327(6) . ?
C12 C13 1.411(7) . ?
C12 C11X 1.427(16) . ?
C13 C14 1.377(7) . ?
C13 H13 0.9500 . ?
C14 C9X 1.431(15) . ?
C14 H14 0.9500 . ?
C14 H14X 0.9500 . ?
O4X C8X 1.280(17) . ?
O5X C8X 1.267(17) . ?
C8X C9X 1.504(15) . ?
C9X C10X 1.416(17) . ?
C10X C11X 1.394(16) . ?
C10X H10X 0.9500 . ?
C11X H11X 0.9500 . ?
O7 C15 1.230(7) . ?
C15 N1 1.324(9) . ?
C15 H15 0.9500 . ?
N1 C17 1.461(11) . ?
N1 C16 1.463(12) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O8 C18 1.248(9) . ?
C18 N2 1.313(11) . ?
C18 H18 0.9500 . ?
N2 C19 1.461(12) . ?
N2 C20 1.466(12) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 O2 98.0(3) . . ?
O4X Co1 O2 89.9(9) . . ?
O4 Co1 O6 150.1(2) . 7_565 ?
O2 Co1 O6 93.55(15) . 7_565 ?
O4 Co1 O3 97.6(3) . 6_556 ?
O2 Co1 O3 98.04(14) . 6_556 ?
O6 Co1 O3 108.01(14) 7_565 6_556 ?
O4 Co1 O7 85.5(3) . . ?
O4X Co1 O7 94.9(9) . . ?
O2 Co1 O7 168.71(15) . . ?
O6 Co1 O7 78.46(15) 7_565 . ?
O3 Co1 O7 92.07(15) 6_556 . ?
O4 Co1 O8 79.8(3) . 8_655 ?
O4X Co1 O8 86.9(8) . 8_655 ?
O2 Co1 O8 87.41(16) . 8_655 ?
O6 Co1 O8 73.24(16) 7_565 8_655 ?
O3 Co1 O8 174.28(16) 6_556 8_655 ?
O7 Co1 O8 82.67(17) . 8_655 ?
O4 Co1 Co2 75.6(2) . . ?
O4X Co1 Co2 65.7(7) . . ?
O2 Co1 Co2 72.28(10) . . ?
O6 Co1 Co2 134.29(10) 7_565 . ?
O3 Co1 Co2 36.97(10) 6_556 . ?
O7 Co1 Co2 119.01(11) . . ?
O8 Co1 Co2 145.23(13) 8_655 . ?
O5X Co2 O1 121.8(7) . . ?
O1 Co2 O6 98.41(15) . 2_564 ?
O1 Co2 O5 99.1(2) . . ?
O6 Co2 O5 140.1(2) 2_564 . ?
O1 Co2 O3 98.34(15) . 6_556 ?
O6 Co2 O3 110.85(14) 2_564 6_556 ?
O5 Co2 O3 101.69(18) . 6_556 ?
O5X Co2 O8 58.1(7) . . ?
O1 Co2 O8 160.39(17) . . ?
O6 Co2 O8 72.42(16) 2_564 . ?
O5 Co2 O8 79.3(2) . . ?
O3 Co2 O8 101.13(16) 6_556 . ?
O5X Co2 Co1 81.7(5) . . ?
O1 Co2 Co1 77.30(11) . . ?
O6 Co2 Co1 144.83(10) 2_564 . ?
O5 Co2 Co1 74.34(17) . . ?
O3 Co2 Co1 37.96(10) 6_556 . ?
O8 Co2 Co1 120.29(13) . . ?
C1 O1 Co2 129.4(3) . . ?
C1 O2 Co1 133.5(3) . . ?
O2 C1 O1 124.8(5) . . ?
O2 C1 C2 118.5(4) . . ?
O1 C1 C2 116.7(4) . . ?
C3 C2 C7 117.7(5) . . ?
C3 C2 C1 120.4(5) . . ?
C7 C2 C1 121.9(5) . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O3 C5 C6 122.2(5) . . ?
O3 C5 C4 120.0(4) . . ?
C6 C5 C4 117.7(5) . . ?
C7 C6 C5 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 121.9(5) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C5 O3 Co2 126.6(3) . 6_656 ?
C5 O3 Co1 128.2(3) . 6_656 ?
Co2 O3 Co1 105.07(15) 6_656 6_656 ?
C8 O4 Co1 130.0(6) . . ?
C8 O5 Co2 131.6(5) . . ?
O5 C8 O4 125.4(7) . . ?
O5 C8 C9 117.7(7) . . ?
O4 C8 C9 116.8(7) . . ?
C14 C9 C10 117.8(6) . . ?
C14 C9 C8 120.0(7) . . ?
C10 C9 C8 122.0(7) . . ?
C11 C10 C9 121.8(7) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 120.1(7) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
O6 C12 C11 122.1(5) . . ?
O6 C12 C13 120.6(5) . . ?
C11 C12 C13 117.1(5) . . ?
O6 C12 C11X 118.6(9) . . ?
C13 C12 C11X 118.5(9) . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 121.6(6) . . ?
C13 C14 C9X 119.1(8) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14X 120.5 . . ?
C9X C14 H14X 120.5 . . ?
C8X O4X Co1 140(2) . . ?
C8X O5X Co2 122.8(12) . . ?
O5X C8X O4X 121.2(17) . . ?
O5X C8X C9X 121.2(14) . . ?
O4X C8X C9X 117.4(15) . . ?
C10X C9X C14 120.2(13) . . ?
C10X C9X C8X 115.0(13) . . ?
C14 C9X C8X 124.7(14) . . ?
C11X C10X C9X 119.5(16) . . ?
C11X C10X H10X 120.3 . . ?
C9X C10X H10X 120.3 . . ?
C10X C11X C12 120.3(15) . . ?
C10X C11X H11X 119.8 . . ?
C12 C11X H11X 119.8 . . ?
C12 O6 Co2 129.6(3) . 2_565 ?
C12 O6 Co1 128.1(3) . 7_566 ?
Co2 O6 Co1 102.07(15) 2_565 7_566 ?
C15 O7 Co1 128.2(4) . . ?
O7 C15 N1 124.4(7) . . ?
O7 C15 H15 117.8 . . ?
N1 C15 H15 117.8 . . ?
C15 N1 C17 121.4(9) . . ?
C15 N1 C16 120.1(7) . . ?
C17 N1 C16 118.4(8) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 O8 Co1 122.4(5) . 8_665 ?
C18 O8 Co2 139.6(6) . . ?
Co1 O8 Co2 84.84(16) 8_665 . ?
O8 C18 N2 128.6(9) . . ?
O8 C18 H18 115.7 . . ?
N2 C18 H18 115.7 . . ?
C18 N2 C19 121.3(8) . . ?
C18 N2 C20 122.3(9) . . ?
C19 N2 C20 116.1(9) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 O2 C1 O1 17.1(8) . . . . ?
Co1 O2 C1 C2 -162.9(4) . . . . ?
Co2 O1 C1 O2 2.0(8) . . . . ?
Co2 O1 C1 C2 -178.1(3) . . . . ?
O2 C1 C2 C3 -179.0(5) . . . . ?
O1 C1 C2 C3 1.0(7) . . . . ?
O2 C1 C2 C7 0.7(8) . . . . ?
O1 C1 C2 C7 -179.3(5) . . . . ?
C7 C2 C3 C4 1.0(8) . . . . ?
C1 C2 C3 C4 -179.3(5) . . . . ?
C2 C3 C4 C5 -1.5(8) . . . . ?
C3 C4 C5 O3 -176.9(5) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
O3 C5 C6 C7 178.0(5) . . . . ?
C4 C5 C6 C7 0.2(8) . . . . ?
C5 C6 C7 C2 -0.8(9) . . . . ?
C3 C2 C7 C6 0.2(8) . . . . ?
C1 C2 C7 C6 -179.5(5) . . . . ?
C6 C5 O3 Co2 -167.3(4) . . . 6_656 ?
C4 C5 O3 Co2 10.5(6) . . . 6_656 ?
C6 C5 O3 Co1 18.9(7) . . . 6_656 ?
C4 C5 O3 Co1 -163.4(4) . . . 6_656 ?
Co2 O5 C8 O4 19.9(15) . . . . ?
Co2 O5 C8 C9 -156.3(6) . . . . ?
Co1 O4 C8 O5 -1.0(18) . . . . ?
Co1 O4 C8 C9 175.3(8) . . . . ?
O5 C8 C9 C14 -175.1(8) . . . . ?
O4 C8 C9 C14 8.4(13) . . . . ?
O5 C8 C9 C10 9.4(13) . . . . ?
O4 C8 C9 C10 -167.2(10) . . . . ?
C14 C9 C10 C11 1.3(13) . . . . ?
C8 C9 C10 C11 177.0(8) . . . . ?
C9 C10 C11 C12 -2.4(12) . . . . ?
C10 C11 C12 O6 -179.2(6) . . . . ?
C10 C11 C12 C13 5.5(10) . . . . ?
O6 C12 C13 C14 176.8(5) . . . . ?
C11 C12 C13 C14 -7.9(9) . . . . ?
C11X C12 C13 C14 14.0(15) . . . . ?
C12 C13 C14 C9 7.1(10) . . . . ?
C12 C13 C14 C9X -10.2(18) . . . . ?
C10 C9 C14 C13 -3.6(12) . . . . ?
C8 C9 C14 C13 -179.4(7) . . . . ?
Co2 O5X C8X O4X -3(4) . . . . ?
Co2 O5X C8X C9X 172(2) . . . . ?
Co1 O4X C8X O5X -33(6) . . . . ?
Co1 O4X C8X C9X 151(3) . . . . ?
C13 C14 C9X C10X 3(3) . . . . ?
C13 C14 C9X C8X 179(2) . . . . ?
O5X C8X C9X C10X 0(4) . . . . ?
O4X C8X C9X C10X 176(3) . . . . ?
O5X C8X C9X C14 -176(3) . . . . ?
O4X C8X C9X C14 0(5) . . . . ?
C14 C9X C10X C11X 1(4) . . . . ?
C8X C9X C10X C11X -176(3) . . . . ?
C9X C10X C11X C12 3(4) . . . . ?
O6 C12 C11X C10X -173.4(18) . . . . ?
C13 C12 C11X C10X -10(3) . . . . ?
C11 C12 O6 Co2 14.4(9) . . . 2_565 ?
C13 C12 O6 Co2 -170.4(4) . . . 2_565 ?
C11X C12 O6 Co2 -7.7(15) . . . 2_565 ?
C11 C12 O6 Co1 -171.3(5) . . . 7_566 ?
C13 C12 O6 Co1 3.8(8) . . . 7_566 ?
C11X C12 O6 Co1 166.5(13) . . . 7_566 ?
Co1 O7 C15 N1 147.4(6) . . . . ?
O7 C15 N1 C17 -177.2(8) . . . . ?
O7 C15 N1 C16 -1.9(12) . . . . ?
Co1 O8 C18 N2 -177.3(8) 8_665 . . . ?
Co2 O8 C18 N2 -51.8(15) . . . . ?
O8 C18 N2 C19 0.4(17) . . . . ?
O8 C18 N2 C20 174.3(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O6 0.95 2.54 3.256(6) 132.1 5_666 yes
C4 H4 O8 0.95 2.45 3.261(7) 142.8 6_656 yes
C6 H6 O6 0.95 2.56 3.389(6) 146.6 4_556 yes
C6 H6 O7 0.95 2.61 3.100(7) 112.4 6_656 yes
C13 H13 O3 0.95 2.65 3.392(7) 135.5 4_456 yes
C11X H11X O1 0.95 2.59 3.23(2) 125.4 2_565 yes
C15 H15 O4 0.95 2.49 2.955(12) 110.1 . yes
C18 H18 O4 0.95 2.20 2.813(13) 121.3 8_665 yes
C18 H18 O4X 0.95 2.39 3.04(3) 124.8 8_665 yes
C19 H19A O3 0.98 2.52 3.487(11) 169.8 6_556 yes

_refine_diff_density_max         1.706
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.158

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide'
####################################################################### 
# 
# 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 2375108'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 Mn2 N2 O8'
_chemical_formula_sum            'C20 H22 Mn2 N2 O8'
_chemical_formula_weight         528.27

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'
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'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.6962(5)
_cell_length_b                   13.0537(4)
_cell_length_c                   19.1273(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4168.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4868
_cell_measurement_theta_min      4.87
_cell_measurement_theta_max      72.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             2160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.051
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    10.323
_shelx_estimated_absorpt_T_min   0.621
_shelx_estimated_absorpt_T_max   0.805
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
; 
Rigaku 007HF diffractometer with HF Varimax confocal mirrors, 
an UG2 goniometer and HyPix Arc-100 detector 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_collimation    0.3
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            42613
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.623
_diffrn_reflns_theta_max         73.689
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4064
_reflns_number_gt                3129
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       
'CrysAlisPro system (CCD 43.115a 64-bit (release 15-03-2024))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1035P)²+9.7771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4064
_refine_ls_number_parameters     402
_refine_ls_number_restraints     578
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.27217(4) 0.22400(6) 0.37495(4) 0.0128(2) Uani 0.952(2) 1 d D U P A 1
Mn2 Mn 0.26844(4) 0.48266(6) 0.36737(4) 0.0123(2) Uani 0.952(2) 1 d D U P A 1
O1 O 0.37286(18) 0.4382(2) 0.31537(18) 0.0254(7) Uani 1 1 d . . . . .
O2 O 0.38476(18) 0.2725(2) 0.33925(18) 0.0243(7) Uani 1 1 d . . . . .
C1 C 0.4084(3) 0.3537(3) 0.3110(2) 0.0186(9) Uani 1 1 d . . . . .
C2 C 0.4854(3) 0.3513(4) 0.2712(2) 0.0197(9) Uani 1 1 d . . . . .
C3 C 0.5163(2) 0.4405(4) 0.2431(2) 0.0204(9) Uani 1 1 d . . . . .
H3 H 0.488358 0.503197 0.249422 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5879(3) 0.4397(4) 0.2054(2) 0.0223(10) Uani 1 1 d . . . . .
H4 H 0.607871 0.501817 0.186296 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6304(3) 0.3492(3) 0.1955(2) 0.0177(9) Uani 1 1 d . . . . .
C6 C 0.5990(3) 0.2594(4) 0.2239(3) 0.0246(10) Uani 1 1 d . . . . .
H6 H 0.626560 0.196458 0.217529 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5275(3) 0.2609(4) 0.2616(3) 0.0236(10) Uani 1 1 d . . . . .
H7 H 0.507347 0.199044 0.280928 0.028 Uiso 1 1 calc R U . . .
O3 O 0.70045(18) 0.3499(2) 0.16089(17) 0.0194(7) Uani 1 1 d . . . . .
O4 O 0.27980(19) 0.2714(2) 0.48042(17) 0.0206(7) Uani 0.952(2) 1 d D U P A 1
O5 O 0.2971(2) 0.4404(2) 0.47105(17) 0.0222(7) Uani 0.952(2) 1 d D U P A 1
C8 C 0.2874(3) 0.3601(3) 0.5069(2) 0.0153(8) Uani 0.952(2) 1 d D U P A 1
C9 C 0.2824(3) 0.3694(3) 0.5840(2) 0.0162(8) Uani 0.952(2) 1 d D U P A 1
C10 C 0.2789(3) 0.4655(4) 0.6171(3) 0.0189(9) Uani 0.952(2) 1 d D U P A 1
H10 H 0.281961 0.525771 0.589383 0.023 Uiso 0.952(2) 1 calc R U P A 1
C11 C 0.2710(3) 0.4746(4) 0.6886(2) 0.0186(9) Uani 0.952(2) 1 d D U P A 1
H11 H 0.266582 0.540652 0.709117 0.022 Uiso 0.952(2) 1 calc R U P A 1
C12 C 0.2695(3) 0.3876(4) 0.7309(2) 0.0157(9) Uani 0.952(2) 1 d D U P A 1
C13 C 0.2742(3) 0.2907(4) 0.6978(2) 0.0195(9) Uani 0.952(2) 1 d D U P A 1
H13 H 0.273830 0.230388 0.725587 0.023 Uiso 0.952(2) 1 calc R U P A 1
C14 C 0.2794(3) 0.2824(4) 0.6264(2) 0.0192(9) Uani 0.952(2) 1 d D U P A 1
H14 H 0.280831 0.216402 0.605486 0.023 Uiso 0.952(2) 1 calc R U P A 1
O6 O 0.2621(2) 0.3950(3) 0.79960(16) 0.0154(7) Uani 0.952(2) 1 d D U P A 1
Mn1X Mn 0.2350(9) 0.2675(11) 0.3680(6) 0.007(3) Uani 0.048(2) 1 d D U P A 2
Mn2X Mn 0.2312(10) 0.5257(12) 0.3743(7) 0.014(3) Uani 0.048(2) 1 d D U P A 2
O4X O 0.206(3) 0.304(3) 0.4726(13) 0.012(3) Uani 0.048(2) 1 d D U P A 2
O5X O 0.225(3) 0.473(3) 0.4785(14) 0.015(3) Uani 0.048(2) 1 d D U P A 2
C8X C 0.211(5) 0.388(2) 0.5071(12) 0.013(3) Uani 0.048(2) 1 d D U P A 2
C9X C 0.220(5) 0.381(3) 0.5842(13) 0.014(3) Uani 0.048(2) 1 d D U P A 2
C10X C 0.221(5) 0.469(3) 0.6272(19) 0.014(4) Uani 0.048(2) 1 d D U P A 2
H10X H 0.212771 0.534280 0.606858 0.017 Uiso 0.048(2) 1 calc R U P A 2
C11X C 0.235(6) 0.462(3) 0.698(2) 0.015(4) Uani 0.048(2) 1 d D U P A 2
H11X H 0.241529 0.522506 0.725005 0.018 Uiso 0.048(2) 1 calc R U P A 2
C12X C 0.239(7) 0.367(3) 0.7317(19) 0.016(4) Uani 0.048(2) 1 d D U P A 2
C13X C 0.229(6) 0.279(3) 0.6891(19) 0.016(4) Uani 0.048(2) 1 d D U P A 2
H13X H 0.225510 0.213040 0.710462 0.019 Uiso 0.048(2) 1 calc R U P A 2
C14X C 0.223(6) 0.286(3) 0.6179(19) 0.014(4) Uani 0.048(2) 1 d D U P A 2
H14X H 0.221626 0.225484 0.590667 0.017 Uiso 0.048(2) 1 calc R U P A 2
O6X O 0.249(5) 0.354(5) 0.8000(19) 0.016(6) Uani 0.048(2) 1 d D U P A 2
O7 O 0.16316(18) 0.1318(2) 0.41038(16) 0.0185(7) Uani 1 1 d . . . . .
C15 C 0.1265(3) 0.1387(3) 0.4666(3) 0.0242(10) Uani 1 1 d . . . . .
H15 H 0.156578 0.148301 0.508266 0.029 Uiso 1 1 calc R U . . .
N1 N 0.0468(3) 0.1334(3) 0.4714(2) 0.0299(10) Uani 1 1 d . . . . .
C16 C -0.0026(3) 0.1199(5) 0.4089(4) 0.0466(16) Uani 1 1 d . . . . .
H16A H -0.027142 0.185486 0.396140 0.070 Uiso 1 1 calc R U . . .
H16B H -0.044717 0.069477 0.418427 0.070 Uiso 1 1 calc R U . . .
H16C H 0.030905 0.095628 0.370214 0.070 Uiso 1 1 calc R U . . .
C17 C 0.0061(4) 0.1489(5) 0.5375(4) 0.0504(18) Uani 1 1 d . . . . .
H17A H 0.045712 0.156267 0.574944 0.076 Uiso 1 1 calc R U . . .
H17B H -0.028421 0.089912 0.547337 0.076 Uiso 1 1 calc R U . . .
H17C H -0.026693 0.211125 0.534892 0.076 Uiso 1 1 calc R U . . .
O8 O 0.16581(18) 0.5716(3) 0.42695(17) 0.0251(7) Uani 1 1 d . . . . .
C18 C 0.1375(3) 0.5733(4) 0.4871(3) 0.0278(11) Uani 1 1 d . . . . .
H18 H 0.139992 0.636842 0.511212 0.033 Uiso 1 1 calc R U . . .
N2 N 0.1041(3) 0.4952(3) 0.5215(2) 0.0322(10) Uani 1 1 d . . . . .
C19 C 0.0975(3) 0.3926(4) 0.4907(3) 0.0359(13) Uani 1 1 d . . . . .
H19A H 0.123843 0.391867 0.444923 0.054 Uiso 1 1 calc R U . A 2
H19B H 0.040801 0.374745 0.485039 0.054 Uiso 1 1 calc R U . A 2
H19C H 0.123304 0.342543 0.521519 0.054 Uiso 1 1 calc R U . A 2
C20 C 0.0757(4) 0.5055(5) 0.5932(3) 0.0449(15) Uani 1 1 d . . . . .
H20A H 0.078615 0.577579 0.607412 0.067 Uiso 1 1 calc R U . . .
H20B H 0.109221 0.464060 0.624278 0.067 Uiso 1 1 calc R U . . .
H20C H 0.020036 0.481954 0.596162 0.067 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 O2 2.098(3) . ?
Mn1 O4 2.114(3) . ?
Mn1 O6 2.125(3) 7_565 ?
Mn1 O3 2.146(3) 6_556 ?
Mn1 O7 2.285(3) . ?
Mn1 O8 2.453(3) 8_655 ?
Mn1 Mn2 3.2258(10) 8_655 ?
Mn2 O1 2.090(3) . ?
Mn2 O5 2.113(3) . ?
Mn2 O6 2.120(3) 2_564 ?
Mn2 O3 2.141(3) 6_556 ?
Mn2 O8 2.363(3) . ?
Mn2 O7 2.403(3) 8_665 ?
O1 C1 1.255(5) . ?
O2 C1 1.253(5) . ?
C1 C2 1.495(6) . ?
C2 C3 1.382(6) . ?
C2 C7 1.385(7) . ?
C3 C4 1.396(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(7) . ?
C4 H4 0.9500 . ?
C5 O3 1.344(5) . ?
C5 C6 1.394(6) . ?
C5 Mn1X 2.379(16) 6_656 ?
C6 C7 1.394(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
O3 Mn1X 1.340(16) 6_656 ?
O3 Mn2X 2.445(15) 6_656 ?
O4 C8 1.270(5) . ?
O5 C8 1.263(5) . ?
C8 C9 1.484(6) . ?
C9 C14 1.397(6) . ?
C9 C10 1.405(6) . ?
C10 C11 1.379(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(7) . ?
C11 H11 0.9500 . ?
C12 O6 1.323(5) . ?
C12 C13 1.416(7) . ?
C13 C14 1.373(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
Mn1X O6X 2.07(5) 7_565 ?
Mn1X O4X 2.114(19) . ?
Mn1X O7 2.287(13) . ?
Mn1X Mn2X 3.208(18) 8_655 ?
Mn2X O8 1.602(16) . ?
Mn2X O5X 2.110(19) . ?
Mn2X O6X 2.14(5) 2_564 ?
Mn2X O7 2.347(14) 8_665 ?
O4X C8X 1.275(19) . ?
O5X C8X 1.264(19) . ?
C8X C9X 1.485(19) . ?
C9X C14X 1.399(19) . ?
C9X C10X 1.407(19) . ?
C10X C11X 1.38(2) . ?
C10X H10X 0.9500 . ?
C11X C12X 1.39(2) . ?
C11X H11X 0.9500 . ?
C12X O6X 1.328(19) . ?
C12X C13X 1.42(2) . ?
C13X C14X 1.37(2) . ?
C13X H13X 0.9500 . ?
C14X H14X 0.9500 . ?
O7 C15 1.241(6) . ?
C15 N1 1.335(7) . ?
C15 H15 0.9500 . ?
N1 C17 1.450(7) . ?
N1 C16 1.464(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O8 C18 1.245(6) . ?
C18 N2 1.335(7) . ?
C18 H18 0.9500 . ?
N2 C20 1.457(7) . ?
N2 C19 1.468(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O2 Mn1 O4 99.68(13) . . ?
O2 Mn1 O6 94.05(13) . 7_565 ?
O4 Mn1 O6 149.99(13) . 7_565 ?
O2 Mn1 O3 99.48(12) . 6_556 ?
O4 Mn1 O3 96.55(13) . 6_556 ?
O6 Mn1 O3 107.39(13) 7_565 6_556 ?
O2 Mn1 O7 165.79(12) . . ?
O4 Mn1 O7 85.37(12) . . ?
O6 Mn1 O7 75.73(12) 7_565 . ?
O3 Mn1 O7 93.08(11) 6_556 . ?
O2 Mn1 O8 89.92(12) . 8_655 ?
O4 Mn1 O8 79.93(12) . 8_655 ?
O6 Mn1 O8 73.50(12) 7_565 8_655 ?
O3 Mn1 O8 170.43(12) 6_556 8_655 ?
O7 Mn1 O8 77.82(11) . 8_655 ?
O2 Mn1 Mn2 117.94(9) . 8_655 ?
O4 Mn1 Mn2 109.98(9) . 8_655 ?
O6 Mn1 Mn2 40.48(9) 7_565 8_655 ?
O3 Mn1 Mn2 128.06(9) 6_556 8_655 ?
O7 Mn1 Mn2 48.05(8) . 8_655 ?
O8 Mn1 Mn2 46.77(8) 8_655 8_655 ?
O1 Mn2 O5 100.66(14) . . ?
O1 Mn2 O6 96.85(13) . 2_564 ?
O5 Mn2 O6 145.60(13) . 2_564 ?
O1 Mn2 O3 95.58(13) . 6_556 ?
O5 Mn2 O3 98.41(13) . 6_556 ?
O6 Mn2 O3 109.14(13) 2_564 6_556 ?
O1 Mn2 O8 166.23(13) . . ?
O5 Mn2 O8 80.80(13) . . ?
O6 Mn2 O8 75.52(12) 2_564 . ?
O3 Mn2 O8 97.76(12) 6_556 . ?
O1 Mn2 O7 89.53(12) . 8_665 ?
O5 Mn2 O7 77.43(11) . 8_665 ?
O6 Mn2 O7 73.32(12) 2_564 8_665 ?
O3 Mn2 O7 173.97(12) 6_556 8_665 ?
O8 Mn2 O7 77.37(11) . 8_665 ?
O1 Mn2 Mn1 117.92(9) . 8_665 ?
O5 Mn2 Mn1 105.08(10) . 8_665 ?
O6 Mn2 Mn1 40.61(9) 2_564 8_665 ?
O3 Mn2 Mn1 133.66(9) 6_556 8_665 ?
O8 Mn2 Mn1 49.15(8) . 8_665 ?
O7 Mn2 Mn1 45.01(7) 8_665 8_665 ?
C1 O1 Mn2 132.1(3) . . ?
C1 O2 Mn1 132.7(3) . . ?
O2 C1 O1 124.4(4) . . ?
O2 C1 C2 118.2(4) . . ?
O1 C1 C2 117.3(4) . . ?
C3 C2 C7 118.5(4) . . ?
C3 C2 C1 120.1(4) . . ?
C7 C2 C1 121.4(4) . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O3 C5 C4 120.3(4) . . ?
O3 C5 C6 121.7(4) . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 Mn1X 145.5(4) . 6_656 ?
C6 C5 Mn1X 95.7(4) . 6_656 ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 C7 C6 121.0(4) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
Mn1X O3 C5 124.9(6) 6_656 . ?
C5 O3 Mn2 126.3(3) . 6_656 ?
C5 O3 Mn1 129.6(3) . 6_656 ?
Mn2 O3 Mn1 104.09(13) 6_656 6_656 ?
C5 O3 Mn2X 109.0(5) . 6_656 ?
Mn1 O3 Mn2X 120.9(4) 6_656 6_656 ?
C8 O4 Mn1 130.8(3) . . ?
C8 O5 Mn2 134.1(3) . . ?
O5 C8 O4 123.6(4) . . ?
O5 C8 C9 118.6(4) . . ?
O4 C8 C9 117.7(4) . . ?
C14 C9 C10 117.6(4) . . ?
C14 C9 C8 120.8(4) . . ?
C10 C9 C8 121.5(4) . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
O6 C12 C11 121.3(4) . . ?
O6 C12 C13 120.9(4) . . ?
C11 C12 C13 117.8(4) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 121.0(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C12 O6 Mn2 133.2(3) . 2_565 ?
C12 O6 Mn1 127.8(3) . 7_566 ?
Mn2 O6 Mn1 98.91(13) 2_565 7_566 ?
O3 Mn1X O6X 114.0(16) 6_556 7_565 ?
O3 Mn1X O4X 96.3(14) 6_556 . ?
O6X Mn1X O4X 143(2) 7_565 . ?
O3 Mn1X O7 122.9(9) 6_556 . ?
O6X Mn1X O7 72(2) 7_565 . ?
O4X Mn1X O7 73.8(11) . . ?
O3 Mn1X C5 27.6(4) 6_556 6_556 ?
O7 Mn1X C5 98.2(5) . 6_556 ?
O3 Mn1X Mn2X 151.8(8) 6_556 8_655 ?
O7 Mn1X Mn2X 47.0(4) . 8_655 ?
C5 Mn1X Mn2X 126.1(5) 6_556 8_655 ?
O8 Mn2X O5X 59.7(15) . . ?
O8 Mn2X O6X 104.4(19) . 2_564 ?
O8 Mn2X O7 96.1(7) . 8_665 ?
O8 Mn2X O3 112.4(7) . 6_556 ?
O7 Mn2X O3 142.4(8) 8_665 6_556 ?
O8 Mn2X Mn1X 77.0(6) . 8_665 ?
O7 Mn2X Mn1X 45.4(4) 8_665 8_665 ?
O3 Mn2X Mn1X 161.7(6) 6_556 8_665 ?
C8X O4X Mn1X 132(2) . . ?
C8X O5X Mn2X 135(2) . . ?
O5X C8X O4X 123(2) . . ?
O5X C8X C9X 118(2) . . ?
O4X C8X C9X 118(2) . . ?
O5X C8X C19 95(4) . . ?
O4X C8X C19 83(4) . . ?
C9X C8X C19 105(5) . . ?
C14X C9X C10X 117(2) . . ?
C14X C9X C8X 121(2) . . ?
C10X C9X C8X 122(2) . . ?
C11X C10X C9X 122(2) . . ?
C11X C10X H10X 119.2 . . ?
C9X C10X H10X 119.2 . . ?
C10X C11X C12X 121(2) . . ?
C10X C11X H11X 119.4 . . ?
C12X C11X H11X 119.4 . . ?
O6X C12X C11X 124(3) . . ?
O6X C12X C13X 119(3) . . ?
C11X C12X C13X 117(2) . . ?
C14X C13X C12X 121(3) . . ?
C14X C13X H13X 119.4 . . ?
C12X C13X H13X 119.4 . . ?
C13X C14X C9X 122(2) . . ?
C13X C14X H14X 119.1 . . ?
C9X C14X H14X 119.1 . . ?
C15 O7 Mn1 127.7(3) . . ?
C15 O7 Mn1X 120.6(4) . . ?
C15 O7 Mn2X 132.0(4) . 8_655 ?
Mn1 O7 Mn2X 68.0(4) . 8_655 ?
C15 O7 Mn2 126.2(3) . 8_655 ?
Mn1 O7 Mn2 86.94(10) . 8_655 ?
O7 C15 N1 123.2(5) . . ?
O7 C15 H15 118.4 . . ?
N1 C15 H15 118.4 . . ?
C15 N1 C17 121.4(5) . . ?
C15 N1 C16 120.8(5) . . ?
C17 N1 C16 117.6(5) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 O8 Mn2X 147.9(6) . . ?
C18 O8 Mn2 136.9(3) . . ?
C18 O8 Mn1 121.4(3) . 8_665 ?
Mn2 O8 Mn1 84.08(10) . 8_665 ?
O8 C18 N2 126.9(5) . . ?
O8 C18 H18 116.5 . . ?
N2 C18 H18 116.5 . . ?
C18 N2 C20 121.9(5) . . ?
C18 N2 C19 122.0(4) . . ?
C20 N2 C19 116.0(5) . . ?
N2 C19 C8X 83.7(9) . . ?
N2 C19 H19A 109.5 . . ?
C8X C19 H19A 72.6 . . ?
N2 C19 H19B 109.5 . . ?
C8X C19 H19B 164.1 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
C8X C19 H19C 56.4 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 O2 C1 O1 21.8(7) . . . . ?
Mn1 O2 C1 C2 -160.3(3) . . . . ?
Mn2 O1 C1 O2 0.9(7) . . . . ?
Mn2 O1 C1 C2 -177.0(3) . . . . ?
O2 C1 C2 C3 -175.8(4) . . . . ?
O1 C1 C2 C3 2.2(7) . . . . ?
O2 C1 C2 C7 4.2(7) . . . . ?
O1 C1 C2 C7 -177.8(4) . . . . ?
C7 C2 C3 C4 0.4(7) . . . . ?
C1 C2 C3 C4 -179.6(4) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C4 C5 O3 -178.1(4) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C3 C4 C5 Mn1X 166.3(7) . . . 6_656 ?
O3 C5 C6 C7 177.9(4) . . . . ?
C4 C5 C6 C7 -0.6(7) . . . . ?
Mn1X C5 C6 C7 -172.6(5) 6_656 . . . ?
C3 C2 C7 C6 -0.5(7) . . . . ?
C1 C2 C7 C6 179.5(4) . . . . ?
C5 C6 C7 C2 0.7(8) . . . . ?
C4 C5 O3 Mn1X -160.8(7) . . . 6_656 ?
C6 C5 O3 Mn1X 20.7(9) . . . 6_656 ?
C4 C5 O3 Mn2 11.8(6) . . . 6_656 ?
C6 C5 O3 Mn2 -166.7(3) . . . 6_656 ?
C4 C5 O3 Mn1 -170.9(3) . . . 6_656 ?
C6 C5 O3 Mn1 10.6(6) . . . 6_656 ?
C4 C5 O3 Mn2X 0.6(6) . . . 6_656 ?
C6 C5 O3 Mn2X -177.9(5) . . . 6_656 ?
Mn1X C5 O3 Mn2X 161.5(8) 6_656 . . 6_656 ?
Mn2 O5 C8 O4 24.5(7) . . . . ?
Mn2 O5 C8 C9 -154.0(3) . . . . ?
Mn1 O4 C8 O5 -4.8(7) . . . . ?
Mn1 O4 C8 C9 173.7(3) . . . . ?
O5 C8 C9 C14 -173.8(4) . . . . ?
O4 C8 C9 C14 7.6(7) . . . . ?
O5 C8 C9 C10 7.6(7) . . . . ?
O4 C8 C9 C10 -171.0(4) . . . . ?
C14 C9 C10 C11 -1.3(7) . . . . ?
C8 C9 C10 C11 177.3(4) . . . . ?
C9 C10 C11 C12 2.6(8) . . . . ?
C10 C11 C12 O6 179.9(4) . . . . ?
C10 C11 C12 C13 -1.6(7) . . . . ?
O6 C12 C13 C14 177.9(4) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C12 C13 C14 C9 1.9(8) . . . . ?
C10 C9 C14 C13 -0.9(7) . . . . ?
C8 C9 C14 C13 -179.5(4) . . . . ?
C11 C12 O6 Mn2 12.1(7) . . . 2_565 ?
C13 C12 O6 Mn2 -166.4(3) . . . 2_565 ?
C11 C12 O6 Mn1 -172.1(3) . . . 7_566 ?
C13 C12 O6 Mn1 9.4(6) . . . 7_566 ?
Mn2X O5X C8X O4X 9(12) . . . . ?
Mn2X O5X C8X C9X 175(5) . . . . ?
Mn2X O5X C8X C19 -76(6) . . . . ?
Mn1X O4X C8X O5X 11(11) . . . . ?
Mn1X O4X C8X C9X -154(5) . . . . ?
Mn1X O4X C8X C19 102(5) . . . . ?
O5X C8X C9X C14X -166(8) . . . . ?
O4X C8X C9X C14X 1(11) . . . . ?
C19 C8X C9X C14X 91(8) . . . . ?
O5X C8X C9X C10X 17(12) . . . . ?
O4X C8X C9X C10X -176(8) . . . . ?
C19 C8X C9X C10X -86(8) . . . . ?
C14X C9X C10X C11X 7(14) . . . . ?
C8X C9X C10X C11X -175(8) . . . . ?
C9X C10X C11X C12X -7(15) . . . . ?
C10X C11X C12X O6X -178(10) . . . . ?
C10X C11X C12X C13X 0(16) . . . . ?
O6X C12X C13X C14X -175(10) . . . . ?
C11X C12X C13X C14X 6(16) . . . . ?
C12X C13X C14X C9X -6(15) . . . . ?
C10X C9X C14X C13X -1(14) . . . . ?
C8X C9X C14X C13X -178(8) . . . . ?
C11X C12X O6X Mn1X 165(8) . . . 7_566 ?
C13X C12X O6X Mn1X -13(16) . . . 7_566 ?
C11X C12X O6X Mn2X -4(16) . . . 2_565 ?
C13X C12X O6X Mn2X 178(7) . . . 2_565 ?
Mn1 O7 C15 N1 139.9(4) . . . . ?
Mn1X O7 C15 N1 115.3(6) . . . . ?
Mn2X O7 C15 N1 -126.8(7) 8_655 . . . ?
Mn2 O7 C15 N1 -101.3(5) 8_655 . . . ?
O7 C15 N1 C17 -175.7(5) . . . . ?
O7 C15 N1 C16 -0.7(8) . . . . ?
O5X Mn2X O8 C18 2.5(18) . . . . ?
O6X Mn2X O8 C18 -151(2) 2_564 . . . ?
O7 Mn2X O8 C18 -80.5(12) 8_665 . . . ?
O3 Mn2X O8 C18 74.4(13) 6_556 . . . ?
Mn1X Mn2X O8 C18 -122.0(10) 8_665 . . . ?
Mn2X O8 C18 N2 -61.9(13) . . . . ?
Mn2 O8 C18 N2 -60.0(7) . . . . ?
Mn1 O8 C18 N2 -178.4(4) 8_665 . . . ?
O8 C18 N2 C20 177.6(5) . . . . ?
O8 C18 N2 C19 0.8(8) . . . . ?
C18 N2 C19 C8X 72.8(9) . . . . ?
C20 N2 C19 C8X -104.2(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O6 0.95 2.57 3.307(6) 134.7 5_666 yes
C4 H4 O8 0.95 2.54 3.327(5) 140.2 6_656 yes
C6 H6 O6 0.95 2.58 3.418(6) 147.4 4_556 yes
C6 H6 O6X 0.95 2.18 2.95(8) 137.6 4_556 yes
C6 H6 O7 0.95 2.66 3.244(6) 120.3 6_656 yes
C11X H11X O1 0.95 2.63 3.15(8) 115.5 2_565 yes
C13X H13X O3 0.95 2.63 3.36(4) 133.9 4_456 yes
C18 H18 O4 0.95 2.29 2.935(6) 124.9 8_665 yes
C19 H19A O3 0.98 2.46 3.416(7) 166.5 6_556 yes

_refine_diff_density_max         1.119
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.123


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide'
