# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_sq_s_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1566883'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H13 Co N5 O4, 0.5(C H3 C N), 2(H2 O)'
_chemical_formula_sum            'C22 H18.50 Co N5.50 O6'
_chemical_formula_weight         514.85

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.0361(16)
_cell_length_b                   10.3968(17)
_cell_length_c                   11.9591(19)
_cell_angle_alpha                81.792(3)
_cell_angle_beta                 67.635(3)
_cell_angle_gamma                77.335(3)
_cell_volume                     1123.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5181
_cell_measurement_theta_min      0.919
_cell_measurement_theta_max      28.406

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.815
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7113
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         28.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5181
_reflns_number_gt                3732
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0109P)²+0.4941P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5181
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.006
_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 -0.13760(3) 0.36272(3) 0.97857(3) 0.03190(10) Uani 1 1 d . . . . .
O1 O 0.08060(16) 0.30446(17) 0.91612(16) 0.0408(4) Uani 1 1 d . . . . .
O2 O 0.17396(18) 0.47515(17) 0.92994(16) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.63918(17) 0.34733(17) 1.01978(16) 0.0401(4) Uani 1 1 d . . . . .
O4 O 0.81211(17) 0.20363(17) 0.90219(16) 0.0428(4) Uani 1 1 d . . . . .
N1 N 0.8443(2) 0.2408(2) 0.14378(18) 0.0357(5) Uani 1 1 d . . . . .
N2 N 0.8350(2) -0.1167(2) 0.4933(2) 0.0490(6) Uani 1 1 d . . . . .
N3 N 0.6243(2) 0.0308(2) 0.56792(19) 0.0417(5) Uani 1 1 d . . . . .
N4 N 0.6332(2) -0.0700(2) 0.65221(18) 0.0378(5) Uani 1 1 d . . . . .
N5 N 0.8545(2) -0.5023(2) 0.8224(2) 0.0440(6) Uani 1 1 d . . . . .
C1 C 0.9211(3) 0.1195(3) 0.1501(2) 0.0445(7) Uani 1 1 d . . . . .
H1 H 0.9967 0.0891 0.0800 0.053 Uiso 1 1 calc R U . . .
C2 C 0.7362(3) 0.2831(3) 0.2461(2) 0.0423(6) Uani 1 1 d . . . . .
H2 H 0.6810 0.3672 0.2438 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7032(3) 0.2077(3) 0.3547(2) 0.0454(7) Uani 1 1 d . . . . .
H3 H 0.6280 0.2414 0.4236 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8957(3) 0.0358(3) 0.2543(2) 0.0459(7) Uani 1 1 d . . . . .
H4 H 0.9520 -0.0483 0.2537 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7828(3) 0.0813(3) 0.3604(2) 0.0407(6) Uani 1 1 d . . . . .
C6 C 0.7477(3) -0.0018(3) 0.4744(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.7593(3) -0.1570(3) 0.6060(2) 0.0408(6) Uani 1 1 d . . . . .
C8 C 0.7971(3) -0.2791(3) 0.6746(2) 0.0411(6) Uani 1 1 d . . . . .
C9 C 0.7042(3) -0.3683(3) 0.7186(3) 0.0678(10) Uani 1 1 d . . . . .
H9 H 0.6202 -0.3555 0.7000 0.081 Uiso 1 1 calc R U . . .
C10 C 0.7357(4) -0.4772(3) 0.7906(3) 0.0697(10) Uani 1 1 d . . . . .
H10 H 0.6714 -0.5368 0.8189 0.084 Uiso 1 1 calc R U . . .
C11 C 0.9416(3) -0.4156(3) 0.7791(3) 0.0684(10) Uani 1 1 d . . . . .
H11 H 1.0244 -0.4297 0.7998 0.082 Uiso 1 1 calc R U . . .
C12 C 0.9198(3) -0.3050(3) 0.7051(3) 0.0676(10) Uani 1 1 d . . . . .
H12 H 0.9875 -0.2484 0.6760 0.081 Uiso 1 1 calc R U . . .
C13 C 0.5196(3) -0.0698(3) 0.7730(2) 0.0408(6) Uani 1 1 d . . . . .
H13A H 0.5459 -0.1453 0.8269 0.049 Uiso 1 1 d R U . . .
H13B H 0.4234 -0.0874 0.7726 0.049 Uiso 1 1 d R U . . .
C14 C 0.4891(3) 0.0582(2) 0.8307(2) 0.0330(5) Uani 1 1 d . . . . .
C15 C 0.5947(3) 0.0944(2) 0.8638(2) 0.0350(6) Uani 1 1 d . . . . .
H15 H 0.6849 0.0389 0.8501 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5654(2) 0.2126(2) 0.9168(2) 0.0321(5) Uani 1 1 d . . . . .
C17 C 0.6787(3) 0.2550(2) 0.9501(2) 0.0334(6) Uani 1 1 d . . . . .
C18 C 0.4319(2) 0.2977(2) 0.9341(2) 0.0328(5) Uani 1 1 d . . . . .
H18 H 0.4138 0.3784 0.9670 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3259(2) 0.2628(2) 0.9024(2) 0.0312(5) Uani 1 1 d . . . . .
C20 C 0.3552(3) 0.1425(2) 0.8524(2) 0.0349(6) Uani 1 1 d . . . . .
H20 H 0.2834 0.1179 0.8330 0.042 Uiso 1 1 calc R U . . .
C21 C 0.1828(2) 0.3552(2) 0.9189(2) 0.0327(5) 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 2.0058(16) . ?
Co1 O2 2.0309(18) 2_567 ?
Co1 O3 2.1405(16) 1_455 ?
Co1 N1 2.158(2) 1_456 ?
Co1 N5 2.187(2) 1_465 ?
Co1 O4 2.2301(17) 1_455 ?
Co1 C17 2.502(2) 1_455 ?
O1 C21 1.265(3) . ?
O2 C21 1.253(3) . ?
O2 Co1 2.0309(17) 2_567 ?
O3 C17 1.258(3) . ?
O3 Co1 2.1405(16) 1_655 ?
O4 C17 1.263(3) . ?
O4 Co1 2.2301(17) 1_655 ?
N1 C2 1.343(3) . ?
N1 C1 1.334(3) . ?
N1 Co1 2.158(2) 1_654 ?
N2 C7 1.330(3) . ?
N2 C6 1.364(3) . ?
N3 C6 1.330(3) . ?
N3 N4 1.359(3) . ?
N4 C7 1.354(3) . ?
N4 C13 1.461(3) . ?
N5 C11 1.308(3) . ?
N5 C10 1.347(3) . ?
N5 Co1 2.187(2) 1_645 ?
C1 C4 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.470(3) . ?
C7 C8 1.468(3) . ?
C8 C9 1.369(4) . ?
C8 C12 1.375(3) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.505(3) . ?
C13 H13A 0.9976 . ?
C13 H13B 1.0237 . ?
C14 C20 1.387(3) . ?
C14 C15 1.399(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C18 1.394(3) . ?
C16 C17 1.504(3) . ?
C17 Co1 2.502(2) 1_655 ?
C18 C19 1.386(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(3) . ?
C19 C21 1.503(3) . ?
C20 H20 0.9300 . ?

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 104.77(7) . 2_567 ?
O1 Co1 O3 156.41(7) . 1_455 ?
O2 Co1 O3 98.41(7) 2_567 1_455 ?
O1 Co1 N1 90.36(7) . 1_456 ?
O2 Co1 N1 89.31(8) 2_567 1_456 ?
O3 Co1 N1 85.54(7) 1_455 1_456 ?
O1 Co1 N5 96.10(8) . 1_465 ?
O2 Co1 N5 87.34(8) 2_567 1_465 ?
O3 Co1 N5 89.22(7) 1_455 1_465 ?
N1 Co1 N5 173.30(8) 1_456 1_465 ?
O1 Co1 O4 96.56(6) . 1_455 ?
O2 Co1 O4 158.67(6) 2_567 1_455 ?
O3 Co1 O4 60.32(6) 1_455 1_455 ?
N1 Co1 O4 90.34(7) 1_456 1_455 ?
N5 Co1 O4 90.68(7) 1_465 1_455 ?
O1 Co1 C17 126.83(8) . 1_455 ?
O2 Co1 C17 128.40(8) 2_567 1_455 ?
O3 Co1 C17 30.18(7) 1_455 1_455 ?
N1 Co1 C17 89.76(7) 1_456 1_455 ?
N5 Co1 C17 87.78(8) 1_465 1_455 ?
O4 Co1 C17 30.28(7) 1_455 1_455 ?
C21 O1 Co1 131.95(17) . . ?
C21 O2 Co1 155.63(17) . 2_567 ?
C17 O3 Co1 91.00(13) . 1_655 ?
C17 O4 Co1 86.84(14) . 1_655 ?
C2 N1 C1 117.0(2) . . ?
C2 N1 Co1 117.62(16) . 1_654 ?
C1 N1 Co1 124.94(18) . 1_654 ?
C7 N2 C6 102.7(2) . . ?
C6 N3 N4 102.7(2) . . ?
C7 N4 N3 109.5(2) . . ?
C7 N4 C13 129.8(2) . . ?
N3 N4 C13 120.6(2) . . ?
C11 N5 C10 115.4(2) . . ?
C11 N5 Co1 120.83(18) . 1_645 ?
C10 N5 Co1 120.87(19) . 1_645 ?
N1 C1 C4 124.3(3) . . ?
N1 C1 H1 117.8 . . ?
C4 C1 H1 117.8 . . ?
N1 C2 C3 123.1(2) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C5 C3 C2 119.7(3) . . ?
C5 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C1 C4 C5 118.1(2) . . ?
C1 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C3 C5 C4 117.9(2) . . ?
C3 C5 C6 120.6(2) . . ?
C4 C5 C6 121.5(2) . . ?
N3 C6 N2 114.8(2) . . ?
N3 C6 C5 121.2(2) . . ?
N2 C6 C5 124.0(2) . . ?
N2 C7 N4 110.3(2) . . ?
N2 C7 C8 127.6(2) . . ?
N4 C7 C8 122.1(2) . . ?
C9 C8 C12 117.0(2) . . ?
C9 C8 C7 120.4(2) . . ?
C12 C8 C7 122.5(2) . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N5 C10 C9 123.7(3) . . ?
N5 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N5 C11 C12 124.8(3) . . ?
N5 C11 H11 117.6 . . ?
C12 C11 H11 117.6 . . ?
C11 C12 C8 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
N4 C13 C14 112.0(2) . . ?
N4 C13 H13A 111.3 . . ?
C14 C13 H13A 109.9 . . ?
N4 C13 H13B 112.5 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 102.1 . . ?
C20 C14 C15 118.7(2) . . ?
C20 C14 C13 120.5(2) . . ?
C15 C14 C13 120.8(2) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C18 C16 C15 119.9(2) . . ?
C18 C16 C17 118.8(2) . . ?
C15 C16 C17 121.1(2) . . ?
O4 C17 O3 121.3(2) . . ?
O4 C17 C16 119.8(2) . . ?
O3 C17 C16 118.8(2) . . ?
O4 C17 Co1 62.88(12) . 1_655 ?
O3 C17 Co1 58.82(11) . 1_655 ?
C16 C17 Co1 169.13(17) . 1_655 ?
C19 C18 C16 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C16 C18 H18 119.8 . . ?
C20 C19 C18 119.1(2) . . ?
C20 C19 C21 120.4(2) . . ?
C18 C19 C21 120.6(2) . . ?
C19 C20 C14 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C14 C20 H20 119.2 . . ?
O2 C21 O1 125.0(2) . . ?
O2 C21 C19 119.1(2) . . ?
O1 C21 C19 115.9(2) . . ?

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
C6 N3 N4 C7 -0.1(3) . . . . ?
C6 N3 N4 C13 177.5(2) . . . . ?
C2 N1 C1 C4 0.4(4) . . . . ?
Co1 N1 C1 C4 -171.4(2) 1_654 . . . ?
C1 N1 C2 C3 0.3(4) . . . . ?
Co1 N1 C2 C3 172.7(2) 1_654 . . . ?
N1 C2 C3 C5 -0.7(4) . . . . ?
N1 C1 C4 C5 -0.5(4) . . . . ?
C2 C3 C5 C4 0.6(4) . . . . ?
C2 C3 C5 C6 -178.8(2) . . . . ?
C1 C4 C5 C3 0.0(4) . . . . ?
C1 C4 C5 C6 179.3(2) . . . . ?
N4 N3 C6 N2 0.0(3) . . . . ?
N4 N3 C6 C5 179.3(2) . . . . ?
C7 N2 C6 N3 0.2(3) . . . . ?
C7 N2 C6 C5 -179.1(2) . . . . ?
C3 C5 C6 N3 12.5(4) . . . . ?
C4 C5 C6 N3 -166.9(3) . . . . ?
C3 C5 C6 N2 -168.2(3) . . . . ?
C4 C5 C6 N2 12.4(4) . . . . ?
C6 N2 C7 N4 -0.3(3) . . . . ?
C6 N2 C7 C8 177.6(3) . . . . ?
N3 N4 C7 N2 0.3(3) . . . . ?
C13 N4 C7 N2 -177.1(2) . . . . ?
N3 N4 C7 C8 -177.8(2) . . . . ?
C13 N4 C7 C8 4.9(4) . . . . ?
N2 C7 C8 C9 -121.2(3) . . . . ?
N4 C7 C8 C9 56.5(4) . . . . ?
N2 C7 C8 C12 63.5(4) . . . . ?
N4 C7 C8 C12 -118.8(3) . . . . ?
C12 C8 C9 C10 0.5(5) . . . . ?
C7 C8 C9 C10 -175.0(3) . . . . ?
C11 N5 C10 C9 -0.5(5) . . . . ?
Co1 N5 C10 C9 160.4(3) 1_645 . . . ?
C8 C9 C10 N5 0.5(6) . . . . ?
C10 N5 C11 C12 -0.4(5) . . . . ?
Co1 N5 C11 C12 -161.4(3) 1_645 . . . ?
N5 C11 C12 C8 1.4(6) . . . . ?
C9 C8 C12 C11 -1.4(5) . . . . ?
C7 C8 C12 C11 174.0(3) . . . . ?
C7 N4 C13 C14 126.0(3) . . . . ?
N3 N4 C13 C14 -51.1(3) . . . . ?
N4 C13 C14 C20 113.0(3) . . . . ?
N4 C13 C14 C15 -67.1(3) . . . . ?
C20 C14 C15 C16 -0.2(4) . . . . ?
C13 C14 C15 C16 180.0(2) . . . . ?
C14 C15 C16 C18 -1.9(4) . . . . ?
C14 C15 C16 C17 -178.4(2) . . . . ?
Co1 O4 C17 O3 -7.4(2) 1_655 . . . ?
Co1 O4 C17 C16 168.0(2) 1_655 . . . ?
Co1 O3 C17 O4 7.7(2) 1_655 . . . ?
Co1 O3 C17 C16 -167.75(19) 1_655 . . . ?
C18 C16 C17 O4 -157.5(2) . . . . ?
C15 C16 C17 O4 19.1(4) . . . . ?
C18 C16 C17 O3 18.0(3) . . . . ?
C15 C16 C17 O3 -165.4(2) . . . . ?
C18 C16 C17 Co1 -56.3(10) . . . 1_655 ?
C15 C16 C17 Co1 120.3(9) . . . 1_655 ?
C15 C16 C18 C19 2.3(4) . . . . ?
C17 C16 C18 C19 178.9(2) . . . . ?
C16 C18 C19 C20 -0.5(4) . . . . ?
C16 C18 C19 C21 -179.0(2) . . . . ?
C18 C19 C20 C14 -1.6(4) . . . . ?
C21 C19 C20 C14 176.8(2) . . . . ?
C15 C14 C20 C19 2.0(4) . . . . ?
C13 C14 C20 C19 -178.2(2) . . . . ?
Co1 O2 C21 O1 94.0(4) 2_567 . . . ?
Co1 O2 C21 C19 -88.6(4) 2_567 . . . ?
Co1 O1 C21 O2 -23.1(4) . . . . ?
Co1 O1 C21 C19 159.48(16) . . . . ?
C20 C19 C21 O2 -159.5(2) . . . . ?
C18 C19 C21 O2 19.0(3) . . . . ?
C20 C19 C21 O1 18.2(3) . . . . ?
C18 C19 C21 O1 -163.4(2) . . . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_p21c_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1566884'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C52 H60 Mn2 N12 O16, 2(C H3 O H), 3(H2 O), 2 (C4 H9 O N)'
_chemical_formula_sum            'C52 H60 Mn2 N12 O16'
_chemical_formula_weight         1219.00

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.108(3)
_cell_length_b                   36.981(10)
_cell_length_c                   15.237(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.592(5)
_cell_angle_gamma                90
_cell_volume                     5599(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13490
_cell_measurement_theta_min      0.977
_cell_measurement_theta_max      28.213

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             2536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35073
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.467
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13490
_reflns_number_gt                9262
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13490
_refine_ls_number_parameters     573
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.020
_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 -0.00486(3) 0.16854(2) 0.31806(2) 0.02631(8) Uani 1 1 d . . . . .
Mn2 Mn 0.28336(3) 0.09875(2) 0.28996(2) 0.02438(7) Uani 1 1 d . . . . .
O5 O 0.28232(14) 0.15466(3) 0.31746(9) 0.0369(3) Uani 1 1 d . . . . .
O6 O 0.16036(12) 0.20376(3) 0.31091(9) 0.0341(3) Uani 1 1 d . . . . .
O4 O 0.10590(13) 0.06775(3) 0.26544(9) 0.0350(3) Uani 1 1 d . . . . .
O3 O 0.00283(14) 0.11165(3) 0.32391(10) 0.0411(4) Uani 1 1 d . . . . .
O2 O -0.49124(14) 0.10117(3) 0.30270(11) 0.0448(4) Uani 1 1 d . . . . .
O1 O -0.58725(13) 0.04857(4) 0.28074(11) 0.0470(4) Uani 1 1 d . . . . .
O7 O 0.77483(15) 0.16662(4) 0.31831(12) 0.0554(4) Uani 1 1 d . . . . .
O8 O 0.86256(13) 0.21978(4) 0.31547(11) 0.0492(4) Uani 1 1 d . . . . .
N5 N -0.30881(16) -0.09043(4) 0.56168(10) 0.0322(4) Uani 1 1 d . . . . .
N1 N -0.7833(3) -0.12678(7) -0.06450(15) 0.0728(7) Uani 1 1 d . . . . .
N3 N -0.39634(18) -0.06420(4) 0.13971(10) 0.0364(4) Uani 1 1 d . . . . .
C7 C -0.3985(2) -0.07774(5) 0.28091(12) 0.0302(4) Uani 1 1 d . . . . .
N2 N -0.50503(17) -0.09371(4) 0.23445(11) 0.0349(4) Uani 1 1 d . . . . .
N6 N 0.35639(16) 0.32454(4) 0.28073(10) 0.0286(4) Uani 1 1 d . . . . .
N9 N 0.18344(17) 0.35539(4) 0.30576(11) 0.0373(4) Uani 1 1 d . . . . .
C31 C 0.2752(2) 0.35000(5) 0.38073(13) 0.0344(5) Uani 1 1 d . . . . .
N10 N 0.06121(17) 0.33230(4) -0.03094(10) 0.0336(4) Uani 1 1 d . . . . .
N13 N 0.26312(18) 0.38645(5) 0.64405(11) 0.0381(4) Uani 1 1 d . . . . .
C21 C 0.00595(18) 0.08083(5) 0.29124(12) 0.0254(4) Uani 1 1 d . . . . .
C25 C 0.62440(18) 0.21626(5) 0.30001(12) 0.0293(4) Uani 1 1 d . . . . .
C14 C -0.22191(18) -0.00053(4) 0.25899(12) 0.0263(4) Uani 1 1 d . . . . .
C19 C -0.11637(17) 0.05770(5) 0.28483(11) 0.0233(4) Uani 1 1 d . . . . .
C18 C -0.23779(18) 0.07261(5) 0.29472(12) 0.0263(4) Uani 1 1 d . . . . .
H18 H -0.2428 0.0970 0.3081 0.032 Uiso 1 1 calc R U . . .
C23 C 0.38809(17) 0.21027(5) 0.29891(11) 0.0240(4) Uani 1 1 d . . . . .
C22 C 0.26883(18) 0.18800(5) 0.30960(11) 0.0240(4) Uani 1 1 d . . . . .
C16 C -0.48478(19) 0.06791(5) 0.29034(13) 0.0312(4) Uani 1 1 d . . . . .
N4 N -0.33117(17) -0.06021(4) 0.22508(10) 0.0322(4) Uani 1 1 d . . . . .
N8 N 0.38199(17) 0.33167(4) 0.36893(10) 0.0339(4) Uani 1 1 d . . . . .
C24 C 0.51535(17) 0.19507(5) 0.30868(12) 0.0270(4) Uani 1 1 d . . . . .
H24 H 0.5272 0.1705 0.3211 0.032 Uiso 1 1 calc R U . . .
C28 C 0.47985(18) 0.26798(5) 0.26872(12) 0.0258(4) Uani 1 1 d . . . . .
C17 C -0.35190(18) 0.05137(5) 0.28483(12) 0.0276(4) Uani 1 1 d . . . . .
C29 C 0.37138(18) 0.24660(5) 0.27905(11) 0.0248(4) Uani 1 1 d . . . . .
H29 H 0.2861 0.2568 0.2725 0.030 Uiso 1 1 calc R U . . .
C15 C -0.34284(18) 0.01480(5) 0.26728(12) 0.0287(4) Uani 1 1 d . . . . .
H15 H -0.4195 0.0004 0.2610 0.034 Uiso 1 1 calc R U . . .
C26 C 0.76270(19) 0.20008(5) 0.31181(14) 0.0354(5) Uani 1 1 d . . . . .
C32 C 0.2367(2) 0.33842(5) 0.24360(13) 0.0306(4) Uani 1 1 d . . . . .
C20 C -0.10917(18) 0.02124(5) 0.26716(12) 0.0270(4) Uani 1 1 d . . . . .
H20 H -0.0272 0.0112 0.2607 0.032 Uiso 1 1 calc R U . . .
C27 C 0.60622(18) 0.25272(5) 0.27998(12) 0.0296(4) Uani 1 1 d . . . . .
H27 H 0.6799 0.2670 0.2741 0.036 Uiso 1 1 calc R U . . .
C37 C 0.0958(2) 0.36339(5) 0.10811(13) 0.0359(5) Uani 1 1 d . . . . .
H37 H 0.0795 0.3838 0.1402 0.043 Uiso 1 1 calc R U . . .
C30 C 0.4621(2) 0.30732(5) 0.24309(13) 0.0313(4) Uani 1 1 d . . . . .
H30A H 0.5461 0.3200 0.2635 0.038 Uiso 1 1 calc R U . . .
H30B H 0.4409 0.3093 0.1785 0.038 Uiso 1 1 calc R U . . .
C42 C 0.1711(2) 0.38673(6) 0.48829(14) 0.0437(5) Uani 1 1 d . . . . .
H42 H 0.1062 0.3958 0.4423 0.052 Uiso 1 1 calc R U . . .
C33 C 0.1742(2) 0.33532(5) 0.14975(12) 0.0312(4) Uani 1 1 d . . . . .
C3 C -0.5989(2) -0.09789(5) 0.07447(14) 0.0400(5) Uani 1 1 d . . . . .
C36 C 0.0428(2) 0.36063(5) 0.01896(13) 0.0369(5) Uani 1 1 d . . . . .
H36 H -0.0091 0.3797 -0.0082 0.044 Uiso 1 1 calc R U . . .
C6 C -0.4993(2) -0.08469(5) 0.14962(13) 0.0345(5) Uani 1 1 d . . . . .
C38 C 0.2647(2) 0.36270(5) 0.47026(13) 0.0368(5) Uani 1 1 d . . . . .
C13 C -0.20600(19) -0.04031(5) 0.24161(14) 0.0344(5) Uani 1 1 d . . . . .
H13A H -0.1623 -0.0430 0.1904 0.041 Uiso 1 1 calc R U . . .
H13B H -0.1474 -0.0509 0.2927 0.041 Uiso 1 1 calc R U . . .
C11 C -0.2589(2) -0.06271(5) 0.52338(14) 0.0424(5) Uani 1 1 d . . . . .
H11 H -0.2040 -0.0465 0.5599 0.051 Uiso 1 1 calc R U . . .
C35 C 0.1316(2) 0.30478(5) 0.01034(13) 0.0395(5) Uani 1 1 d . . . . .
H35 H 0.1429 0.2843 -0.0228 0.047 Uiso 1 1 calc R U . . .
C34 C 0.1879(2) 0.30514(5) 0.09889(13) 0.0398(5) Uani 1 1 d . . . . .
H34 H 0.2354 0.2851 0.1249 0.048 Uiso 1 1 calc R U . . .
C10 C -0.3861(2) -0.11335(6) 0.50823(14) 0.0408(5) Uani 1 1 d . . . . .
H10 H -0.4215 -0.1331 0.5337 0.049 Uiso 1 1 calc R U . . .
C5 C -0.6795(4) -0.10767(9) -0.07908(18) 0.0855(10) Uani 1 1 d . . . . .
H5 H -0.6687 -0.1044 -0.1379 0.103 Uiso 1 1 calc R U . . .
C39 C 0.3578(3) 0.35044(7) 0.54205(14) 0.0564(7) Uani 1 1 d . . . . .
H39 H 0.4229 0.3337 0.5333 0.068 Uiso 1 1 calc R U . . .
C4 C -0.5862(3) -0.09226(7) -0.01270(16) 0.0668(8) Uani 1 1 d . . . . .
H4 H -0.5161 -0.0783 -0.0264 0.080 Uiso 1 1 calc R U . . .
C2 C -0.7048(2) -0.11833(6) 0.09015(15) 0.0491(6) Uani 1 1 d . . . . .
H2 H -0.7159 -0.1232 0.1483 0.059 Uiso 1 1 calc R U . . .
C1 C -0.7945(3) -0.13155(7) 0.01885(17) 0.0622(7) Uani 1 1 d . . . . .
H1 H -0.8677 -0.1447 0.0305 0.075 Uiso 1 1 calc R U . . .
C12 C -0.2830(2) -0.05653(5) 0.43331(13) 0.0414(5) Uani 1 1 d . . . . .
H12 H -0.2461 -0.0365 0.4098 0.050 Uiso 1 1 calc R U . . .
C9 C -0.4165(2) -0.10936(5) 0.41753(13) 0.0391(5) Uani 1 1 d . . . . .
H9 H -0.4725 -0.1259 0.3828 0.047 Uiso 1 1 calc R U . . .
C8 C -0.3634(2) -0.08060(5) 0.37790(12) 0.0312(4) Uani 1 1 d . . . . .
C41 C 0.1731(2) 0.39753(6) 0.57518(14) 0.0442(5) Uani 1 1 d . . . . .
H41 H 0.1071 0.4136 0.5859 0.053 Uiso 1 1 calc R U . . .
C40 C 0.3540(3) 0.36295(7) 0.62568(15) 0.0549(7) Uani 1 1 d . . . . .
H40 H 0.4187 0.3546 0.6727 0.066 Uiso 1 1 calc R U . . .
O21 O -0.02957(19) 0.16558(6) 0.17619(11) 0.0654(5) Uani 1 1 d D . . . .
H21A H -0.1015 0.1558 0.1560 0.098 Uiso 1 1 calc DR U . . .
H21B H -0.0126(18) 0.1807(5) 0.1402(14) 0.063(9) Uiso 1 1 d 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 O3 2.1065(14) . ?
Mn1 O21 2.1328(17) . ?
Mn1 O6 2.1365(13) . ?
Mn1 O7 2.2287(16) 1_455 ?
Mn1 N10 2.2750(17) 4_566 ?
Mn1 O8 2.3171(15) 1_455 ?
Mn1 C26 2.609(2) 1_455 ?
Mn2 O5 2.1101(14) . ?
Mn2 O4 2.1035(13) . ?
Mn2 N5 2.2487(17) 3_556 ?
Mn2 O2 2.2526(15) 1_655 ?
Mn2 N13 2.2621(17) 4_565 ?
Mn2 O1 2.2893(15) 1_655 ?
Mn2 C16 2.605(2) 1_655 ?
O5 C22 1.244(2) . ?
O6 C22 1.245(2) . ?
O4 C21 1.247(2) . ?
O3 C21 1.246(2) . ?
O2 C16 1.248(2) . ?
O2 Mn2 2.2526(15) 1_455 ?
O1 C16 1.245(2) . ?
O1 Mn2 2.2894(15) 1_455 ?
O7 C26 1.246(2) . ?
O7 Mn1 2.2287(16) 1_655 ?
O8 C26 1.238(2) . ?
O8 Mn1 2.3171(15) 1_655 ?
N5 C10 1.326(2) . ?
N5 C11 1.325(2) . ?
N5 Mn2 2.2488(17) 3_556 ?
N1 C1 1.307(3) . ?
N1 C5 1.318(4) . ?
N3 C6 1.318(3) . ?
N3 N4 1.354(2) . ?
C7 N2 1.315(2) . ?
C7 N4 1.349(2) . ?
C7 C8 1.459(3) . ?
N2 C6 1.346(2) . ?
N6 C32 1.340(2) . ?
N6 N8 1.347(2) . ?
N6 C30 1.449(2) . ?
N9 C32 1.330(2) . ?
N9 C31 1.347(2) . ?
C31 N8 1.315(2) . ?
C31 C38 1.465(3) . ?
N10 C36 1.327(2) . ?
N10 C35 1.331(2) . ?
N10 Mn1 2.2750(17) 4_565 ?
N13 C41 1.321(3) . ?
N13 C40 1.331(3) . ?
N13 Mn2 2.2621(17) 4_566 ?
C21 C19 1.492(2) . ?
C25 C27 1.387(3) . ?
C25 C24 1.379(2) . ?
C25 C26 1.501(3) . ?
C14 C20 1.382(2) . ?
C14 C15 1.374(2) . ?
C14 C13 1.508(2) . ?
C19 C18 1.379(2) . ?
C19 C20 1.379(2) . ?
C18 C17 1.380(2) . ?
C18 H18 0.9300 . ?
C23 C29 1.381(2) . ?
C23 C24 1.387(2) . ?
C23 C22 1.493(2) . ?
C16 C17 1.492(2) . ?
C16 Mn2 2.606(2) 1_455 ?
N4 C13 1.445(2) . ?
C24 H24 0.9300 . ?
C28 C29 1.384(2) . ?
C28 C27 1.378(2) . ?
C28 C30 1.509(2) . ?
C17 C15 1.385(2) . ?
C29 H29 0.9300 . ?
C15 H15 0.9300 . ?
C26 Mn1 2.609(2) 1_655 ?
C32 C33 1.458(3) . ?
C20 H20 0.9300 . ?
C27 H27 0.9300 . ?
C37 C36 1.369(3) . ?
C37 C33 1.387(3) . ?
C37 H37 0.9300 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C42 C38 1.363(3) . ?
C42 C41 1.379(3) . ?
C42 H42 0.9300 . ?
C33 C34 1.380(3) . ?
C3 C4 1.374(3) . ?
C3 C2 1.367(3) . ?
C3 C6 1.463(3) . ?
C36 H36 0.9300 . ?
C38 C39 1.382(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C35 C34 1.365(3) . ?
C35 H35 0.9300 . ?
C34 H34 0.9300 . ?
C10 C9 1.367(3) . ?
C10 H10 0.9300 . ?
C5 C4 1.373(3) . ?
C5 H5 0.9300 . ?
C39 C40 1.363(3) . ?
C39 H39 0.9300 . ?
C4 H4 0.9300 . ?
C2 C1 1.371(3) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C12 C8 1.383(3) . ?
C12 H12 0.9300 . ?
C9 C8 1.379(3) . ?
C9 H9 0.9300 . ?
C41 H41 0.9300 . ?
C40 H40 0.9300 . ?
O21 H21A 0.8200 . ?
O21 H21B 0.824(12) . ?

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
O3 Mn1 O21 89.32(7) . . ?
O3 Mn1 O6 126.01(5) . . ?
O21 Mn1 O6 85.79(6) . . ?
O3 Mn1 O7 89.85(5) . 1_455 ?
O21 Mn1 O7 93.97(7) . 1_455 ?
O6 Mn1 O7 144.10(5) . 1_455 ?
O3 Mn1 N10 86.67(6) . 4_566 ?
O21 Mn1 N10 169.19(7) . 4_566 ?
O6 Mn1 N10 88.45(6) . 4_566 ?
O7 Mn1 N10 96.06(6) 1_455 4_566 ?
O3 Mn1 O8 146.53(5) . 1_455 ?
O21 Mn1 O8 93.73(7) . 1_455 ?
O6 Mn1 O8 87.45(5) . 1_455 ?
O7 Mn1 O8 56.70(5) 1_455 1_455 ?
N10 Mn1 O8 95.15(6) 4_566 1_455 ?
O3 Mn1 C26 118.30(6) . 1_455 ?
O21 Mn1 C26 92.81(7) . 1_455 ?
O6 Mn1 C26 115.63(6) . 1_455 ?
O7 Mn1 C26 28.47(5) 1_455 1_455 ?
N10 Mn1 C26 97.93(6) 4_566 1_455 ?
O8 Mn1 C26 28.31(5) 1_455 1_455 ?
O5 Mn2 O4 122.28(5) . . ?
O5 Mn2 N5 86.46(5) . 3_556 ?
O4 Mn2 N5 92.31(6) . 3_556 ?
O5 Mn2 O2 89.19(5) . 1_655 ?
O4 Mn2 O2 148.53(5) . 1_655 ?
N5 Mn2 O2 89.53(6) 3_556 1_655 ?
O5 Mn2 N13 87.43(6) . 4_565 ?
O4 Mn2 N13 92.13(6) . 4_565 ?
N5 Mn2 N13 173.73(6) 3_556 4_565 ?
O2 Mn2 N13 88.99(6) 1_655 4_565 ?
O5 Mn2 O1 146.11(5) . 1_655 ?
O4 Mn2 O1 91.46(5) . 1_655 ?
N5 Mn2 O1 89.41(6) 3_556 1_655 ?
O2 Mn2 O1 57.13(5) 1_655 1_655 ?
N13 Mn2 O1 94.90(6) 4_565 1_655 ?
O5 Mn2 C16 117.76(6) . 1_655 ?
O4 Mn2 C16 119.95(6) . 1_655 ?
N5 Mn2 C16 90.07(6) 3_556 1_655 ?
O2 Mn2 C16 28.60(5) 1_655 1_655 ?
N13 Mn2 C16 91.54(6) 4_565 1_655 ?
O1 Mn2 C16 28.54(5) 1_655 1_655 ?
C22 O5 Mn2 163.07(12) . . ?
C22 O6 Mn1 114.47(11) . . ?
C21 O4 Mn2 116.52(12) . . ?
C21 O3 Mn1 154.13(13) . . ?
C16 O2 Mn2 91.61(11) . 1_455 ?
C16 O1 Mn2 89.98(12) . 1_455 ?
C26 O7 Mn1 92.99(12) . 1_655 ?
C26 O8 Mn1 89.08(12) . 1_655 ?
C10 N5 C11 116.95(17) . . ?
C10 N5 Mn2 118.40(13) . 3_556 ?
C11 N5 Mn2 124.49(13) . 3_556 ?
C1 N1 C5 116.7(2) . . ?
C6 N3 N4 101.98(15) . . ?
N2 C7 N4 109.53(17) . . ?
N2 C7 C8 122.37(18) . . ?
N4 C7 C8 128.09(17) . . ?
C7 N2 C6 103.31(17) . . ?
C32 N6 N8 109.83(15) . . ?
C32 N6 C30 132.47(16) . . ?
N8 N6 C30 117.40(15) . . ?
C32 N9 C31 103.21(17) . . ?
N8 C31 N9 114.50(17) . . ?
N8 C31 C38 119.62(18) . . ?
N9 C31 C38 125.88(19) . . ?
C36 N10 C35 116.84(17) . . ?
C36 N10 Mn1 122.96(13) . 4_565 ?
C35 N10 Mn1 119.96(13) . 4_565 ?
C41 N13 C40 115.90(18) . . ?
C41 N13 Mn2 129.05(14) . 4_566 ?
C40 N13 Mn2 115.04(14) . 4_566 ?
O3 C21 O4 124.19(17) . . ?
O3 C21 C19 117.97(16) . . ?
O4 C21 C19 117.82(16) . . ?
C27 C25 C24 119.86(17) . . ?
C27 C25 C26 119.79(17) . . ?
C24 C25 C26 120.36(16) . . ?
C20 C14 C15 118.95(16) . . ?
C20 C14 C13 118.11(16) . . ?
C15 C14 C13 122.94(17) . . ?
C18 C19 C20 119.48(16) . . ?
C18 C19 C21 120.48(16) . . ?
C20 C19 C21 120.03(16) . . ?
C19 C18 C17 120.22(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C29 C23 C24 119.45(17) . . ?
C29 C23 C22 119.46(16) . . ?
C24 C23 C22 121.09(16) . . ?
O6 C22 O5 122.94(17) . . ?
O6 C22 C23 118.32(16) . . ?
O5 C22 C23 118.73(16) . . ?
O2 C16 O1 121.23(18) . . ?
O2 C16 C17 119.02(17) . . ?
O1 C16 C17 119.74(17) . . ?
O2 C16 Mn2 59.79(10) . 1_455 ?
O1 C16 Mn2 61.48(10) . 1_455 ?
C17 C16 Mn2 176.27(14) . 1_455 ?
C7 N4 N3 109.93(16) . . ?
C7 N4 C13 131.43(16) . . ?
N3 N4 C13 118.60(16) . . ?
C31 N8 N6 103.02(15) . . ?
C23 C24 C25 120.10(17) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C29 C28 C27 119.18(16) . . ?
C29 C28 C30 121.42(16) . . ?
C27 C28 C30 119.39(17) . . ?
C15 C17 C18 119.54(17) . . ?
C15 C17 C16 120.21(17) . . ?
C18 C17 C16 120.23(16) . . ?
C23 C29 C28 120.88(17) . . ?
C23 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C14 C15 C17 120.81(17) . . ?
C14 C15 H15 119.6 . . ?
C17 C15 H15 119.6 . . ?
O7 C26 O8 120.89(18) . . ?
O7 C26 C25 118.79(18) . . ?
O8 C26 C25 120.32(17) . . ?
O7 C26 Mn1 58.54(10) . 1_655 ?
O8 C26 Mn1 62.61(11) . 1_655 ?
C25 C26 Mn1 174.47(14) . 1_655 ?
N6 C32 N9 109.41(17) . . ?
N6 C32 C33 125.38(17) . . ?
N9 C32 C33 125.21(18) . . ?
C14 C20 C19 120.98(17) . . ?
C14 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C25 C27 C28 120.51(17) . . ?
C25 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C36 C37 C33 118.97(18) . . ?
C36 C37 H37 120.5 . . ?
C33 C37 H37 120.5 . . ?
N6 C30 C28 112.50(15) . . ?
N6 C30 H30A 109.1 . . ?
C28 C30 H30A 109.1 . . ?
N6 C30 H30B 109.1 . . ?
C28 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
C38 C42 C41 119.6(2) . . ?
C38 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C34 C33 C37 117.16(18) . . ?
C34 C33 C32 122.97(17) . . ?
C37 C33 C32 119.87(17) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 C6 122.2(2) . . ?
C2 C3 C6 119.8(2) . . ?
N10 C36 C37 123.83(18) . . ?
N10 C36 H36 118.1 . . ?
C37 C36 H36 118.1 . . ?
N3 C6 N2 115.24(17) . . ?
N3 C6 C3 123.13(18) . . ?
N2 C6 C3 121.60(19) . . ?
C42 C38 C39 116.85(19) . . ?
C42 C38 C31 124.64(19) . . ?
C39 C38 C31 118.49(19) . . ?
N4 C13 C14 114.14(16) . . ?
N4 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N4 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N5 C11 C12 123.99(18) . . ?
N5 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
N10 C35 C34 123.31(18) . . ?
N10 C35 H35 118.3 . . ?
C34 C35 H35 118.3 . . ?
C33 C34 C35 119.75(18) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
N5 C10 C9 123.32(19) . . ?
N5 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C4 C5 N1 124.0(3) . . ?
C4 C5 H5 118.0 . . ?
N1 C5 H5 118.0 . . ?
C40 C39 C38 119.8(2) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C1 C2 124.0(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C11 C12 C8 118.76(19) . . ?
C11 C12 H12 120.6 . . ?
C8 C12 H12 120.6 . . ?
C8 C9 C10 119.50(18) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C8 C12 117.46(18) . . ?
C9 C8 C7 117.24(17) . . ?
C12 C8 C7 125.30(18) . . ?
N13 C41 C42 124.0(2) . . ?
N13 C41 H41 118.0 . . ?
C42 C41 H41 118.0 . . ?
C39 C40 N13 123.9(2) . . ?
C39 C40 H40 118.1 . . ?
N13 C40 H40 118.1 . . ?
Mn1 O21 H21A 109.5 . . ?
Mn1 O21 H21B 129.8(15) . . ?
H21A O21 H21B 109.2 . . ?

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
N4 C7 N2 C6 -0.7(2) . . . . ?
C8 C7 N2 C6 -179.30(17) . . . . ?
C32 N9 C31 N8 1.4(2) . . . . ?
C32 N9 C31 C38 -178.87(19) . . . . ?
Mn1 O3 C21 O4 72.9(4) . . . . ?
Mn1 O3 C21 C19 -108.8(3) . . . . ?
Mn2 O4 C21 O3 5.5(2) . . . . ?
Mn2 O4 C21 C19 -172.81(11) . . . . ?
O3 C21 C19 C18 14.9(3) . . . . ?
O4 C21 C19 C18 -166.72(17) . . . . ?
O3 C21 C19 C20 -166.37(17) . . . . ?
O4 C21 C19 C20 12.0(2) . . . . ?
C20 C19 C18 C17 -1.6(3) . . . . ?
C21 C19 C18 C17 177.15(16) . . . . ?
Mn1 O6 C22 O5 -4.3(2) . . . . ?
Mn1 O6 C22 C23 176.24(11) . . . . ?
Mn2 O5 C22 O6 84.9(5) . . . . ?
Mn2 O5 C22 C23 -95.7(4) . . . . ?
C29 C23 C22 O6 -8.5(2) . . . . ?
C24 C23 C22 O6 171.41(16) . . . . ?
C29 C23 C22 O5 172.00(16) . . . . ?
C24 C23 C22 O5 -8.1(2) . . . . ?
Mn2 O2 C16 O1 -2.5(2) 1_455 . . . ?
Mn2 O2 C16 C17 175.94(15) 1_455 . . . ?
Mn2 O1 C16 O2 2.5(2) 1_455 . . . ?
Mn2 O1 C16 C17 -175.97(16) 1_455 . . . ?
N2 C7 N4 N3 1.1(2) . . . . ?
C8 C7 N4 N3 179.60(17) . . . . ?
N2 C7 N4 C13 -176.50(18) . . . . ?
C8 C7 N4 C13 2.0(3) . . . . ?
C6 N3 N4 C7 -1.0(2) . . . . ?
C6 N3 N4 C13 176.97(16) . . . . ?
N9 C31 N8 N6 -0.6(2) . . . . ?
C38 C31 N8 N6 179.60(17) . . . . ?
C32 N6 N8 C31 -0.4(2) . . . . ?
C30 N6 N8 C31 174.09(16) . . . . ?
C29 C23 C24 C25 1.0(3) . . . . ?
C22 C23 C24 C25 -178.90(16) . . . . ?
C27 C25 C24 C23 -1.1(3) . . . . ?
C26 C25 C24 C23 179.12(17) . . . . ?
C19 C18 C17 C15 1.7(3) . . . . ?
C19 C18 C17 C16 -176.48(16) . . . . ?
O2 C16 C17 C15 -177.18(18) . . . . ?
O1 C16 C17 C15 1.3(3) . . . . ?
O2 C16 C17 C18 1.0(3) . . . . ?
O1 C16 C17 C18 179.52(18) . . . . ?
C24 C23 C29 C28 0.0(3) . . . . ?
C22 C23 C29 C28 180.00(16) . . . . ?
C27 C28 C29 C23 -1.1(3) . . . . ?
C30 C28 C29 C23 177.31(16) . . . . ?
C20 C14 C15 C17 -0.9(3) . . . . ?
C13 C14 C15 C17 178.84(17) . . . . ?
C18 C17 C15 C14 -0.5(3) . . . . ?
C16 C17 C15 C14 177.75(17) . . . . ?
Mn1 O7 C26 O8 -6.0(2) 1_655 . . . ?
Mn1 O7 C26 C25 174.40(16) 1_655 . . . ?
Mn1 O8 C26 O7 5.8(2) 1_655 . . . ?
Mn1 O8 C26 C25 -174.65(17) 1_655 . . . ?
C27 C25 C26 O7 -170.86(19) . . . . ?
C24 C25 C26 O7 8.9(3) . . . . ?
C27 C25 C26 O8 9.5(3) . . . . ?
C24 C25 C26 O8 -170.69(19) . . . . ?
N8 N6 C32 N9 1.3(2) . . . . ?
C30 N6 C32 N9 -172.09(18) . . . . ?
N8 N6 C32 C33 -178.48(17) . . . . ?
C30 N6 C32 C33 8.1(3) . . . . ?
C31 N9 C32 N6 -1.5(2) . . . . ?
C31 N9 C32 C33 178.22(18) . . . . ?
C15 C14 C20 C19 1.1(3) . . . . ?
C13 C14 C20 C19 -178.71(17) . . . . ?
C18 C19 C20 C14 0.2(3) . . . . ?
C21 C19 C20 C14 -178.56(16) . . . . ?
C24 C25 C27 C28 0.1(3) . . . . ?
C26 C25 C27 C28 179.84(17) . . . . ?
C29 C28 C27 C25 1.0(3) . . . . ?
C30 C28 C27 C25 -177.40(17) . . . . ?
C32 N6 C30 C28 -113.9(2) . . . . ?
N8 N6 C30 C28 73.2(2) . . . . ?
C29 C28 C30 N6 34.4(2) . . . . ?
C27 C28 C30 N6 -147.19(17) . . . . ?
C36 C37 C33 C34 -3.4(3) . . . . ?
C36 C37 C33 C32 177.16(19) . . . . ?
N6 C32 C33 C34 34.5(3) . . . . ?
N9 C32 C33 C34 -145.3(2) . . . . ?
N6 C32 C33 C37 -146.1(2) . . . . ?
N9 C32 C33 C37 34.1(3) . . . . ?
C35 N10 C36 C37 2.5(3) . . . . ?
Mn1 N10 C36 C37 -171.85(16) 4_565 . . . ?
C33 C37 C36 N10 0.4(3) . . . . ?
N4 N3 C6 N2 0.6(2) . . . . ?
N4 N3 C6 C3 -177.64(18) . . . . ?
C7 N2 C6 N3 0.1(2) . . . . ?
C7 N2 C6 C3 178.29(18) . . . . ?
C4 C3 C6 N3 5.4(3) . . . . ?
C2 C3 C6 N3 -178.4(2) . . . . ?
C4 C3 C6 N2 -172.7(2) . . . . ?
C2 C3 C6 N2 3.5(3) . . . . ?
C41 C42 C38 C39 0.0(3) . . . . ?
C41 C42 C38 C31 -178.2(2) . . . . ?
N8 C31 C38 C42 168.6(2) . . . . ?
N9 C31 C38 C42 -11.1(3) . . . . ?
N8 C31 C38 C39 -9.6(3) . . . . ?
N9 C31 C38 C39 170.7(2) . . . . ?
C7 N4 C13 C14 -90.4(2) . . . . ?
N3 N4 C13 C14 92.2(2) . . . . ?
C20 C14 C13 N4 -174.05(16) . . . . ?
C15 C14 C13 N4 6.2(3) . . . . ?
C10 N5 C11 C12 0.3(3) . . . . ?
Mn2 N5 C11 C12 -175.09(17) 3_556 . . . ?
C36 N10 C35 C34 -2.3(3) . . . . ?
Mn1 N10 C35 C34 172.17(17) 4_565 . . . ?
C37 C33 C34 C35 3.5(3) . . . . ?
C32 C33 C34 C35 -177.0(2) . . . . ?
N10 C35 C34 C33 -0.7(3) . . . . ?
C11 N5 C10 C9 -0.6(3) . . . . ?
Mn2 N5 C10 C9 175.10(17) 3_556 . . . ?
C1 N1 C5 C4 -1.3(5) . . . . ?
C42 C38 C39 C40 -1.0(4) . . . . ?
C31 C38 C39 C40 177.3(2) . . . . ?
N1 C5 C4 C3 2.0(5) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C6 C3 C4 C5 175.6(3) . . . . ?
C4 C3 C2 C1 -1.4(4) . . . . ?
C6 C3 C2 C1 -177.7(2) . . . . ?
C5 N1 C1 C2 -0.8(4) . . . . ?
C3 C2 C1 N1 2.2(4) . . . . ?
N5 C11 C12 C8 -0.6(3) . . . . ?
N5 C10 C9 C8 1.1(3) . . . . ?
C10 C9 C8 C12 -1.3(3) . . . . ?
C10 C9 C8 C7 179.70(19) . . . . ?
C11 C12 C8 C9 1.0(3) . . . . ?
C11 C12 C8 C7 179.9(2) . . . . ?
N2 C7 C8 C9 20.9(3) . . . . ?
N4 C7 C8 C9 -157.4(2) . . . . ?
N2 C7 C8 C12 -158.0(2) . . . . ?
N4 C7 C8 C12 23.7(3) . . . . ?
C40 N13 C41 C42 -1.3(3) . . . . ?
Mn2 N13 C41 C42 179.61(16) 4_566 . . . ?
C38 C42 C41 N13 1.3(4) . . . . ?
C38 C39 C40 N13 1.0(4) . . . . ?
C41 N13 C40 C39 0.1(4) . . . . ?
Mn2 N13 C40 C39 179.4(2) 4_566 . . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3



