# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1869399'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Co2 N17'
_chemical_formula_weight         482.18

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   11.1688(3)
_cell_length_b                   12.1405(3)
_cell_length_c                   6.0137(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.111(2)
_cell_angle_gamma                90
_cell_volume                     812.18(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3299
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_F_000             478
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.086
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3299
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             985
_reflns_number_gt                771
_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       'NONIUS COLLECT'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0423P)²+0.6866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         985
_refine_ls_number_parameters     78
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Co Co 0.2500 0.2500 1.0000 0.01688(17) Uani 1 2 d S . P . .
N1 N 0.09000(19) 0.33695(18) 0.9114(4) 0.0242(5) Uani 1 1 d . . . . .
N2 N 0.0000 0.3352(2) 1.0000 0.0207(6) Uani 1 2 d S T P . .
N3 N 0.1986(2) 0.2243(2) 1.3295(3) 0.0272(5) Uani 1 1 d . . . . .
N4 N 0.2500 0.2500 1.5000 0.0202(6) Uani 1 2 d S . P . .
N5 N 0.16063(17) 0.09749(17) 0.8902(3) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.1984(3) 0.0000 0.9707(6) 0.0201(7) Uani 1 2 d S T P . .
H1 H 0.2568 0.0000 1.0956 0.024 Uiso 1 2 calc R U P . .
C2 C 0.0406(3) 0.0000 0.6037(5) 0.0162(7) Uani 1 2 d S T P . .
C3 C 0.0808(2) 0.0970(2) 0.7085(4) 0.0183(5) Uani 1 1 d . . . . .
H3 H 0.0510 0.1654 0.6498 0.022 Uiso 1 1 calc R U . . .
N6 N 0.3529(8) 0.0000 1.5707(14) 0.049(2) Uani 0.5 2 d S T P . .
C4 C 0.4384(5) 0.0000 1.5340(8) 0.0403(10) Uani 1 2 d S T P . .


_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
Co N1 2.103(2) 7_557 ?
Co N1 2.103(2) . ?
Co N3 2.135(2) 7_557 ?
Co N3 2.135(2) . ?
Co N5 2.178(2) . ?
Co N5 2.178(2) 7_557 ?
N1 N2 1.179(2) . ?
N2 N1 1.179(2) 2_557 ?
N3 N4 1.172(2) . ?
N4 N3 1.172(2) 7_558 ?
N5 C1 1.333(3) . ?
N5 C3 1.347(3) . ?
C1 N5 1.333(3) 6 ?
C2 C3 1.392(3) 6 ?
C2 C3 1.392(3) . ?
C2 C2 1.475(6) 5_556 ?
N6 C4 1.000(8) . ?
C4 C4 1.470(11) 5_658 ?

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 Co N1 180.0 7_557 . ?
N1 Co N3 90.92(9) 7_557 7_557 ?
N1 Co N3 89.08(9) . 7_557 ?
N1 Co N3 89.08(9) 7_557 . ?
N1 Co N3 90.92(9) . . ?
N3 Co N3 180.0 7_557 . ?
N1 Co N5 90.36(7) 7_557 . ?
N1 Co N5 89.64(7) . . ?
N3 Co N5 89.82(8) 7_557 . ?
N3 Co N5 90.18(8) . . ?
N1 Co N5 89.64(7) 7_557 7_557 ?
N1 Co N5 90.36(7) . 7_557 ?
N3 Co N5 90.18(8) 7_557 7_557 ?
N3 Co N5 89.82(8) . 7_557 ?
N5 Co N5 180.00(6) . 7_557 ?
N2 N1 Co 128.02(18) . . ?
N1 N2 N1 177.9(4) . 2_557 ?
N4 N3 Co 128.46(15) . . ?
N3 N4 N3 180.0 7_558 . ?
C1 N5 C3 117.1(2) . . ?
C1 N5 Co 121.54(18) . . ?
C3 N5 Co 120.11(16) . . ?
N5 C1 N5 125.2(3) 6 . ?
C3 C2 C3 115.7(3) 6 . ?
C3 C2 C2 122.15(14) 6 5_556 ?
C3 C2 C2 122.15(14) . 5_556 ?
N5 C3 C2 122.3(2) . . ?
N6 C4 C4 176.7(8) . 5_658 ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1869400'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 Co N10'
_chemical_formula_weight         301.16

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   15.7824(17)
_cell_length_b                   6.3744(6)
_cell_length_c                   10.4133(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.150(2)
_cell_angle_gamma                90
_cell_volume                     1041.58(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2788
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      30.70

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3659
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1199
_reflns_number_gt                1112
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0268P)²+1.3747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1199
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0517
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_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 0.2500 0.2500 0.0000 0.00868(9) Uani 1 2 d S . P . .
N5 N 0.32383(7) 0.15819(18) -0.16202(11) 0.0107(2) Uani 1 1 d . . . . .
N4 N 0.32075(7) 0.04713(19) 0.14623(11) 0.0116(2) Uani 1 1 d . . . . .
N2 N 0.12247(7) -0.09446(19) 0.00570(11) 0.0143(2) Uani 1 1 d . . . . .
N1 N 0.16328(8) 0.0156(2) -0.05550(12) 0.0155(3) Uani 1 1 d . . . . .
N3 N 0.08067(10) -0.2046(2) 0.06227(14) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.40848(8) 0.1807(2) -0.16168(13) 0.0109(3) Uani 1 1 d . . . . .
H1 H 0.4381 0.2624 -0.0978 0.013 Uiso 1 1 calc R U . . .
C2 C 0.45293(8) 0.0862(2) -0.25329(12) 0.0103(3) Uani 1 1 d . . . . .
C3 C 0.40579(8) 0.0315(2) 0.15244(13) 0.0123(3) Uani 1 1 d . . . . .
H3 H 0.4341 0.1019 0.0915 0.015 Uiso 1 1 calc R U . . .
C4 C 0.28360(8) -0.0494(2) 0.23995(13) 0.0117(3) Uani 1 1 d . . . . .
H4 H 0.2246 -0.0398 0.2365 0.014 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 N1 2.0664(12) . ?
Co1 N1 2.0664(12) 7 ?
Co1 N4 2.2077(12) . ?
Co1 N4 2.2077(12) 7 ?
Co1 N5 2.2289(11) 7 ?
Co1 N5 2.2289(11) . ?
N5 C4 1.3368(18) 6 ?
N5 C1 1.3434(17) . ?
N4 C3 1.3404(17) . ?
N4 C4 1.3407(17) . ?
N2 N3 1.1655(18) . ?
N2 N1 1.1837(17) . ?
C1 C2 1.3815(19) . ?
C2 C3 1.3869(19) 6 ?
C2 C2 1.480(2) 2_654 ?
C3 C2 1.3869(19) 6_556 ?
C4 N5 1.3368(18) 6_556 ?

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 Co1 N1 180.0 . 7 ?
N1 Co1 N4 92.31(5) . . ?
N1 Co1 N4 87.69(5) 7 . ?
N1 Co1 N4 87.69(5) . 7 ?
N1 Co1 N4 92.31(5) 7 7 ?
N4 Co1 N4 180.00(4) . 7 ?
N1 Co1 N5 90.99(4) . 7 ?
N1 Co1 N5 89.01(4) 7 7 ?
N4 Co1 N5 84.17(4) . 7 ?
N4 Co1 N5 95.83(4) 7 7 ?
N1 Co1 N5 89.01(4) . . ?
N1 Co1 N5 90.99(4) 7 . ?
N4 Co1 N5 95.83(4) . . ?
N4 Co1 N5 84.17(4) 7 . ?
N5 Co1 N5 180.0 7 . ?
C4 N5 C1 116.64(11) 6 . ?
C4 N5 Co1 118.04(9) 6 . ?
C1 N5 Co1 124.77(9) . . ?
C3 N4 C4 116.39(12) . . ?
C3 N4 Co1 120.45(9) . . ?
C4 N4 Co1 122.86(9) . . ?
N3 N2 N1 177.78(15) . . ?
N2 N1 Co1 131.32(10) . . ?
N5 C1 C2 122.00(12) . . ?
C1 C2 C3 116.81(12) . 6 ?
C1 C2 C2 123.33(13) . 2_654 ?
C3 C2 C2 119.51(12) 6 2_654 ?
N4 C3 C2 122.20(12) . 6_556 ?
N5 C4 N4 125.80(12) 6_556 . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.057

_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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1869402'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N30 Ni3 O2'
_chemical_formula_weight         938.79

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'
Ni Ni 0.3393 1.1124 '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                   7.912(4)
_cell_length_b                   10.297(6)
_cell_length_c                   10.861(6)
_cell_angle_alpha                106.636(7)
_cell_angle_beta                 90.289(8)
_cell_angle_gamma                100.046(8)
_cell_volume                     833.3(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2932
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      29.96

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.758
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5654
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7487
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2907
_reflns_number_gt                2365
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0597P)²+1.0312P] 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         2907
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Ni1 Ni 0.5000 1.0000 0.5000 0.0132(2) Uani 1 2 d S . P . .
Ni2 Ni 0.87918(6) 0.99628(5) 0.87476(4) 0.01266(18) Uani 1 1 d . . . . .
N7 N 0.4501(5) 1.0268(4) 0.6945(3) 0.0222(8) Uani 1 1 d . . . . .
N12 N 0.9071(5) 0.9411(3) 0.6777(3) 0.0180(8) Uani 1 1 d . . . . .
N13 N 0.8827(4) 1.0498(3) 1.0804(3) 0.0159(7) Uani 1 1 d . . . . .
N11 N 0.7991(4) 0.9166(3) 0.5948(3) 0.0139(7) Uani 1 1 d . . . . .
N5 N 1.0014(4) 1.1949(3) 0.8750(3) 0.0162(7) Uani 1 1 d . . . . .
N3 N 0.7493(4) 0.7941(3) 0.8544(3) 0.0150(7) Uani 1 1 d . . . . .
N1 N 0.3284(4) 0.8116(3) 0.4485(3) 0.0170(8) Uani 1 1 d . . . . .
N14 N 0.8219(4) 1.1439(3) 1.1475(3) 0.0157(8) Uani 1 1 d . . . . .
N2 N 0.0559(5) 0.6854(4) 0.4745(4) 0.0244(9) Uani 1 1 d . . . . .
N6 N 1.2140(5) 1.3383(3) 0.7966(4) 0.0249(9) Uani 1 1 d . . . . .
N10 N 0.6971(5) 0.8897(4) 0.5091(3) 0.0226(8) Uani 1 1 d . . . . .
C6 C 0.7865(5) 0.6816(4) 0.7666(4) 0.0165(9) Uani 1 1 d . . . . .
H6 H 0.8650 0.6932 0.7055 0.020 Uiso 1 1 calc R U . . .
N4 N 0.5498(5) 0.6505(3) 0.9434(3) 0.0240(9) Uani 1 1 d . . . . .
C1 C 0.2484(5) 0.5747(4) 0.3285(4) 0.0166(9) Uani 1 1 d . . . . .
C9 C 1.0276(5) 1.4388(4) 0.9559(4) 0.0159(9) Uani 1 1 d . . . . .
C8 C 0.5950(6) 0.5399(4) 0.8594(4) 0.0211(10) Uani 1 1 d . . . . .
H8 H 0.5466 0.4527 0.8646 0.025 Uiso 1 1 calc R U . . .
N15 N 0.7632(6) 1.2337(4) 1.2104(4) 0.0309(10) Uani 1 1 d . . . . .
C5 C 0.7104(5) 0.5497(4) 0.7655(4) 0.0153(9) Uani 1 1 d . . . . .
C2 C 0.3653(5) 0.6976(4) 0.3632(4) 0.0170(9) Uani 1 1 d . . . . .
H2 H 0.4716 0.7017 0.3269 0.020 Uiso 1 1 calc R U . . .
C12 C 0.9472(6) 1.3064(4) 0.9492(4) 0.0172(9) Uani 1 1 d . . . . .
H12 H 0.8523 1.2943 0.9976 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6294(6) 0.7727(4) 0.9359(4) 0.0204(9) Uani 1 1 d . . . . .
H7 H 0.5988 0.8502 0.9927 0.024 Uiso 1 1 calc R U . . .
C3 C 0.1756(6) 0.7990(4) 0.5008(4) 0.0204(9) Uani 1 1 d . . . . .
H3 H 0.1511 0.8769 0.5611 0.025 Uiso 1 1 calc R U . . .
C11 C 1.1339(6) 1.2162(4) 0.8030(4) 0.0206(9) Uani 1 1 d . . . . .
H11 H 1.1733 1.1389 0.7531 0.025 Uiso 1 1 calc R U . . .
C4 C 0.0923(6) 0.5742(4) 0.3870(4) 0.0219(10) Uani 1 1 d . . . . .
H4 H 0.0101 0.4937 0.3644 0.026 Uiso 1 1 calc R U . . .
C10 C 1.1597(6) 1.4488(4) 0.8732(4) 0.0244(10) Uani 1 1 d . . . . .
H10 H 1.2127 1.5360 0.8707 0.029 Uiso 1 1 calc R U . . .
N8 N 0.5506(4) 1.0422(3) 0.7800(3) 0.0146(7) Uani 1 1 d . . . . .
N9 N 0.6439(5) 1.0603(4) 0.8694(3) 0.0223(8) Uani 1 1 d . . . . .
O1 O 0.3500(10) 0.4903(7) 0.5825(7) 0.135(3) Uiso 1 1 d . . . . .
H1A H 0.2352 0.4745 0.5494 0.162 Uiso 1 1 d R U . . .
H1B H 0.4082 0.5654 0.5461 0.162 Uiso 1 1 d 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
Ni1 N1 2.091(3) . ?
Ni1 N1 2.091(3) 2_676 ?
Ni1 N7 2.099(4) . ?
Ni1 N7 2.099(4) 2_676 ?
Ni1 N10 2.101(4) . ?
Ni1 N10 2.101(4) 2_676 ?
Ni2 N12 2.074(3) . ?
Ni2 N9 2.086(4) . ?
Ni2 N5 2.103(3) . ?
Ni2 N3 2.104(3) . ?
Ni2 N13 2.109(4) 2_777 ?
Ni2 N13 2.140(3) . ?
N7 N8 1.177(5) . ?
N12 N11 1.180(5) . ?
N13 N14 1.210(4) . ?
N13 Ni2 2.109(4) 2_777 ?
N11 N10 1.167(5) . ?
N5 C11 1.336(6) . ?
N5 C12 1.341(5) . ?
N3 C7 1.334(5) . ?
N3 C6 1.352(5) . ?
N1 C3 1.340(5) . ?
N1 C2 1.349(5) . ?
N14 N15 1.153(5) . ?
N2 C3 1.329(6) . ?
N2 C4 1.338(5) . ?
N6 C11 1.326(6) . ?
N6 C10 1.343(5) . ?
C6 C5 1.383(6) . ?
C6 H6 0.9300 . ?
N4 C7 1.329(5) . ?
N4 C8 1.345(5) . ?
C1 C2 1.384(6) . ?
C1 C4 1.392(6) . ?
C1 C5 1.480(5) 2_666 ?
C9 C12 1.381(6) . ?
C9 C10 1.391(6) . ?
C9 C9 1.484(7) 2_787 ?
C8 C5 1.386(6) . ?
C8 H8 0.9300 . ?
C5 C1 1.480(5) 2_666 ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?
N8 N9 1.168(5) . ?
O1 H1B 1.0098 . ?
O1 H1A 0.9448 . ?
O1 H1B 1.0098 . ?

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 Ni1 N1 180.00(17) . 2_676 ?
N1 Ni1 N7 90.25(14) . . ?
N1 Ni1 N7 89.75(14) 2_676 . ?
N1 Ni1 N7 89.75(14) . 2_676 ?
N1 Ni1 N7 90.25(14) 2_676 2_676 ?
N7 Ni1 N7 180.0 . 2_676 ?
N1 Ni1 N10 87.81(14) . . ?
N1 Ni1 N10 92.19(14) 2_676 . ?
N7 Ni1 N10 92.76(14) . . ?
N7 Ni1 N10 87.24(14) 2_676 . ?
N1 Ni1 N10 92.19(14) . 2_676 ?
N1 Ni1 N10 87.81(14) 2_676 2_676 ?
N7 Ni1 N10 87.24(14) . 2_676 ?
N7 Ni1 N10 92.76(14) 2_676 2_676 ?
N10 Ni1 N10 180.0 . 2_676 ?
N12 Ni2 N9 96.58(14) . . ?
N12 Ni2 N5 85.71(13) . . ?
N9 Ni2 N5 88.25(14) . . ?
N12 Ni2 N3 88.88(13) . . ?
N9 Ni2 N3 89.99(14) . . ?
N5 Ni2 N3 174.08(13) . . ?
N12 Ni2 N13 94.51(13) . 2_777 ?
N9 Ni2 N13 168.68(13) . 2_777 ?
N5 Ni2 N13 90.34(13) . 2_777 ?
N3 Ni2 N13 92.48(13) . 2_777 ?
N12 Ni2 N13 172.87(13) . . ?
N9 Ni2 N13 90.45(13) . . ?
N5 Ni2 N13 93.33(13) . . ?
N3 Ni2 N13 92.33(13) . . ?
N13 Ni2 N13 78.42(14) 2_777 . ?
N8 N7 Ni1 127.0(3) . . ?
N11 N12 Ni2 127.7(3) . . ?
N14 N13 Ni2 123.6(3) . 2_777 ?
N14 N13 Ni2 124.4(3) . . ?
Ni2 N13 Ni2 101.58(14) 2_777 . ?
N10 N11 N12 177.1(4) . . ?
C11 N5 C12 117.3(3) . . ?
C11 N5 Ni2 122.5(3) . . ?
C12 N5 Ni2 120.2(3) . . ?
C7 N3 C6 117.1(3) . . ?
C7 N3 Ni2 119.3(2) . . ?
C6 N3 Ni2 123.6(3) . . ?
C3 N1 C2 116.9(3) . . ?
C3 N1 Ni1 120.7(2) . . ?
C2 N1 Ni1 122.4(3) . . ?
N15 N14 N13 179.4(4) . . ?
C3 N2 C4 116.4(4) . . ?
C11 N6 C10 116.4(4) . . ?
N11 N10 Ni1 125.0(3) . . ?
N3 C6 C5 121.5(4) . . ?
N3 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C7 N4 C8 115.9(4) . . ?
C2 C1 C4 116.7(3) . . ?
C2 C1 C5 121.1(4) . 2_666 ?
C4 C1 C5 122.2(4) . 2_666 ?
C12 C9 C10 115.6(3) . . ?
C12 C9 C9 121.4(5) . 2_787 ?
C10 C9 C9 122.9(5) . 2_787 ?
N4 C8 C5 123.0(4) . . ?
N4 C8 H8 118.5 . . ?
C5 C8 H8 118.5 . . ?
C6 C5 C8 116.2(3) . . ?
C6 C5 C1 122.3(4) . 2_666 ?
C8 C5 C1 121.4(4) . 2_666 ?
N1 C2 C1 121.4(4) . . ?
N1 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N5 C12 C9 122.1(4) . . ?
N5 C12 H12 118.9 . . ?
C9 C12 H12 118.9 . . ?
N4 C7 N3 126.0(4) . . ?
N4 C7 H7 117.0 . . ?
N3 C7 H7 117.0 . . ?
N2 C3 N1 126.0(3) . . ?
N2 C3 H3 117.0 . . ?
N1 C3 H3 117.0 . . ?
N6 C11 N5 125.5(4) . . ?
N6 C11 H11 117.3 . . ?
N5 C11 H11 117.3 . . ?
N2 C4 C1 122.5(4) . . ?
N2 C4 H4 118.8 . . ?
C1 C4 H4 118.8 . . ?
N6 C10 C9 123.0(4) . . ?
N6 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N9 N8 N7 176.3(4) . . ?
N8 N9 Ni2 128.1(3) . . ?
H1B O1 H1A 102.4 . . ?
H1B O1 H1B 0.0 . . ?
H1A O1 H1B 102.4 . . ?

_refine_diff_density_max         0.971
_refine_diff_density_min         -1.064
_refine_diff_density_rms         0.117

_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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1869401'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 Mn N10'
_chemical_formula_weight         297.17

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'
Mn Mn 0.3368 0.7283 '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                   14.6496(11)
_cell_length_b                   7.5253(6)
_cell_length_c                   20.2225(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2229.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7435
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.49

_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.188
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18239
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         30.601
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3363
_reflns_number_gt                2632
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0286P)²+0.8029P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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 0.10349(2) 0.18403(3) 0.32190(2) 0.01157(7) Uani 1 1 d . . . . .
N7 N 0.30403(9) 0.31969(16) 0.34611(6) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.09701(10) 0.20471(19) 0.16093(8) 0.0136(3) Uani 1 1 d . . . . .
H1 H 0.0428 0.2656 0.1687 0.016 Uiso 1 1 calc R U . . .
N4 N 0.05842(8) 0.54814(17) 0.26003(6) 0.0137(3) Uani 1 1 d . . . . .
N3 N 0.08266(10) 0.47145(18) 0.30770(7) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.14982(9) 0.16000(17) 0.21242(6) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.09679(11) 0.2469(2) 0.47833(8) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.1598 0.2423 0.4731 0.020 Uiso 1 1 calc R U . . .
N5 N -0.03586(9) 0.13028(19) 0.28663(7) 0.0185(3) Uani 1 1 d . . . . .
N9 N 0.25839(9) 0.0328(2) 0.13844(7) 0.0229(3) Uani 1 1 d . . . . .
N10 N -0.08851(9) 0.2552(2) 0.49361(7) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.04353(9) 0.20968(17) 0.42642(6) 0.0163(3) Uani 1 1 d . . . . .
N6 N 0.24027(9) 0.23441(19) 0.36100(7) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.12087(10) 0.1627(2) 0.09607(8) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.06131(10) 0.29207(19) 0.53975(8) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.20361(11) 0.0749(2) 0.08790(8) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.2217 0.0441 0.0453 0.024 Uiso 1 1 calc R U . . .
C6 C -0.03387(11) 0.2972(2) 0.54429(8) 0.0172(3) Uani 1 1 d . . . . .
H6 H -0.0603 0.3313 0.5841 0.021 Uiso 1 1 calc R U . . .
C7 C -0.04690(11) 0.2131(2) 0.43702(8) 0.0194(3) Uani 1 1 d . . . . .
H7 H -0.0842 0.1832 0.4015 0.023 Uiso 1 1 calc R U . . .
N8 N 0.12950(9) -0.10138(18) 0.33209(7) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.22830(11) 0.0767(2) 0.19830(8) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.2654 0.0467 0.2339 0.023 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 N6 2.1874(13) . ?
Mn1 N8 2.1911(14) . ?
Mn1 N5 2.1999(13) . ?
Mn1 N3 2.2031(14) . ?
Mn1 N1 2.2970(13) . ?
Mn1 N2 2.3226(13) . ?
N7 N6 1.1725(18) . ?
N7 N8 1.1754(18) 8_665 ?
C1 N2 1.340(2) . ?
C1 C3 1.394(2) . ?
C1 H1 0.9300 . ?
N4 N5 1.1755(18) 3 ?
N4 N3 1.1784(18) . ?
N2 C8 1.340(2) . ?
C2 N1 1.338(2) . ?
C2 C4 1.389(2) . ?
C2 H2 0.9300 . ?
N5 N4 1.1755(18) 3_545 ?
N9 C8 1.330(2) . ?
N9 C5 1.338(2) . ?
N10 C7 1.335(2) . ?
N10 C6 1.338(2) . ?
N1 C7 1.342(2) . ?
C3 C5 1.390(2) . ?
C3 C4 1.475(2) 7_565 ?
C4 C6 1.398(2) . ?
C4 C3 1.475(2) 7_566 ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N8 N7 1.1754(18) 8_655 ?
C8 H8 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
N6 Mn1 N8 88.66(5) . . ?
N6 Mn1 N5 177.68(5) . . ?
N8 Mn1 N5 90.67(5) . . ?
N6 Mn1 N3 90.22(5) . . ?
N8 Mn1 N3 177.10(5) . . ?
N5 Mn1 N3 90.56(5) . . ?
N6 Mn1 N1 90.18(5) . . ?
N8 Mn1 N1 93.57(5) . . ?
N5 Mn1 N1 87.65(5) . . ?
N3 Mn1 N1 89.11(5) . . ?
N6 Mn1 N2 95.18(5) . . ?
N8 Mn1 N2 87.85(5) . . ?
N5 Mn1 N2 87.01(5) . . ?
N3 Mn1 N2 89.58(5) . . ?
N1 Mn1 N2 174.49(5) . . ?
N6 N7 N8 176.85(15) . 8_665 ?
N2 C1 C3 121.97(14) . . ?
N2 C1 H1 119.0 . . ?
C3 C1 H1 119.0 . . ?
N5 N4 N3 177.47(16) 3 . ?
N4 N3 Mn1 128.99(11) . . ?
C8 N2 C1 116.55(14) . . ?
C8 N2 Mn1 119.35(11) . . ?
C1 N2 Mn1 123.53(10) . . ?
N1 C2 C4 122.34(14) . . ?
N1 C2 H2 118.8 . . ?
C4 C2 H2 118.8 . . ?
N4 N5 Mn1 128.16(11) 3_545 . ?
C8 N9 C5 115.96(14) . . ?
C7 N10 C6 116.07(14) . . ?
C2 N1 C7 116.50(14) . . ?
C2 N1 Mn1 121.12(10) . . ?
C7 N1 Mn1 121.74(11) . . ?
N7 N6 Mn1 137.04(12) . . ?
C5 C3 C1 116.00(14) . . ?
C5 C3 C4 122.26(14) . 7_565 ?
C1 C3 C4 121.73(14) . 7_565 ?
C2 C4 C6 116.04(14) . . ?
C2 C4 C3 121.73(14) . 7_566 ?
C6 C4 C3 122.21(14) . 7_566 ?
N9 C5 C3 123.01(15) . . ?
N9 C5 H5 118.5 . . ?
C3 C5 H5 118.5 . . ?
N10 C6 C4 122.65(15) . . ?
N10 C6 H6 118.7 . . ?
C4 C6 H6 118.7 . . ?
N10 C7 N1 126.32(15) . . ?
N10 C7 H7 116.8 . . ?
N1 C7 H7 116.8 . . ?
N7 N8 Mn1 131.47(11) 8_655 . ?
N9 C8 N2 126.47(15) . . ?
N9 C8 H8 116.8 . . ?
N2 C8 H8 116.8 . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3

