# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_tjd209_2_chunk_0m
_database_code_depnum_ccdc_archive 'CCDC 1439545'
_audit_update_record             
;
2015-12-27 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
_audit_creation_date             2015-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H7 Cu N9'
_chemical_formula_sum            'C11 H7 Cu N9'
_chemical_formula_weight         328.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.7773(5)
_cell_length_b                   20.7006(16)
_cell_length_c                   8.3965(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.2110(10)
_cell_angle_gamma                90
_cell_volume                     1177.72(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5202
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.864
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1535 before and 0.0312 after correction.
The Ratio of minimum to maximum transmission is 0.8916.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7088
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.968
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1997
_reflns_number_total             2155
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²+1.5496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(N6) \\sim Ueq, Uanis(N8) \\sim Ueq, Uanis(C1) \\sim
Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C3(H3), C7(H7), C2(H2), C8(H8), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.8409(3) 0.20973(12) 0.6495(3) 0.0182(6) Uani 1 1 d . . . . .
N7 N 1.1393(4) 0.22026(11) 0.9157(4) 0.0198(6) Uani 1 1 d . . . . .
N2 N 0.8349(3) 0.33345(12) 0.6538(3) 0.0162(5) Uani 1 1 d . U . . .
N1 N 1.1049(3) 0.36001(11) 0.8086(3) 0.0172(5) Uani 1 1 d . . . . .
N6 N 0.5947(4) 0.19409(12) 0.5400(3) 0.0210(6) Uani 1 1 d . U . . .
N5 N 0.6683(4) 0.13664(12) 0.5730(3) 0.0226(6) Uani 1 1 d . . . . .
N4 N 0.8145(4) 0.14586(12) 0.6396(3) 0.0210(6) Uani 1 1 d . . . . .
C11 C 0.7035(4) 0.23783(14) 0.5882(4) 0.0174(6) Uani 1 1 d . . . . .
C10 C 0.6966(4) 0.30849(14) 0.5866(4) 0.0181(6) Uani 1 1 d . . . . .
C9 C 0.5723(4) 0.34778(15) 0.5296(4) 0.0228(7) Uani 1 1 d . . . . .
H9 H 0.4617 0.3317 0.4754 0.027 Uiso 1 1 calc R . . . .
N8 N 1.1652(4) 0.16422(12) 0.8790(3) 0.0193(5) Uani 1 1 d . U . . .
C6 C 0.8583(4) 0.39696(13) 0.6722(4) 0.0163(6) Uani 1 1 d . . . . .
C5 C 1.0177(4) 0.41288(15) 0.7571(3) 0.0162(6) Uani 1 1 d . . . . .
C4 C 1.0757(4) 0.47490(13) 0.7842(4) 0.0213(7) Uani 1 1 d . . . . .
H4 H 1.0041 0.5097 0.7435 0.026 Uiso 1 1 calc R . . . .
N9 N 1.1956(4) 0.11087(13) 0.8551(4) 0.0277(6) Uani 1 1 d . . . . .
C3 C 1.2269(5) 0.48280(15) 0.8648(4) 0.0250(7) Uani 1 1 d . . . . .
H3 H 1.2758 0.5237 0.8887 0.030 Uiso 1 1 calc R . . . .
C7 C 0.7378(4) 0.43988(15) 0.6156(4) 0.0224(7) Uani 1 1 d . . . . .
H7 H 0.7554 0.4842 0.6265 0.027 Uiso 1 1 calc R . . . .
C2 C 1.3169(5) 0.42909(15) 0.9162(4) 0.0250(7) Uani 1 1 d . . . . .
H2 H 1.4321 0.4337 0.9773 0.030 Uiso 1 1 calc R . . . .
C8 C 0.5943(4) 0.41406(15) 0.5443(4) 0.0249(7) Uani 1 1 d . . . . .
H8 H 0.4977 0.4406 0.4991 0.030 Uiso 1 1 calc R . . . .
C1 C 1.2519(4) 0.36817(14) 0.8854(4) 0.0191(6) Uani 1 1 d . U . . .
H1 H 1.3226 0.3329 0.9244 0.023 Uiso 1 1 calc R . . . .
Cu1 Cu 1.00639(4) 0.27400(2) 0.73890(4) 0.01667(19) 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
N3 N4 1.336(4) . ?
N3 C11 1.204(4) . ?
N3 Cu1 1.886(3) . ?
N7 N8 1.214(4) . ?
N7 Cu1 2.048(3) . ?
N2 C10 1.201(4) . ?
N2 C6 1.333(4) . ?
N2 Cu1 1.828(2) . ?
N1 C5 1.313(4) . ?
N1 C1 1.187(4) . ?
N1 Cu1 1.986(2) . ?
N6 N5 1.317(4) . ?
N6 C11 1.231(4) . ?
N5 N4 1.144(4) . ?
C11 C10 1.464(4) . ?
C11 Cu1 2.503(3) . ?
C10 C9 1.258(4) . ?
C10 Cu1 2.538(3) . ?
C9 C8 1.385(4) . ?
N8 N9 1.142(4) . ?
C6 C5 1.323(4) . ?
C6 C7 1.290(4) . ?
C5 C4 1.360(4) . ?
C4 C3 1.227(5) . ?
C3 C2 1.335(5) . ?
C7 C8 1.251(5) . ?
C2 C1 1.359(4) . ?

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
N4 N3 Cu1 143.1(2) . . ?
C11 N3 N4 110.5(3) . . ?
C11 N3 Cu1 106.1(2) . . ?
N8 N7 Cu1 113.5(2) . . ?
C10 N2 C6 124.7(3) . . ?
C10 N2 Cu1 112.2(2) . . ?
C6 N2 Cu1 123.1(2) . . ?
C5 N1 Cu1 120.3(2) . . ?
C1 N1 C5 115.3(3) . . ?
C1 N1 Cu1 124.1(2) . . ?
C11 N6 N5 111.9(3) . . ?
N4 N5 N6 105.8(2) . . ?
N5 N4 N3 108.0(3) . . ?
N3 C11 N6 103.7(3) . . ?
N3 C11 C10 120.7(3) . . ?
N3 C11 Cu1 46.38(16) . . ?
N6 C11 C10 135.5(3) . . ?
N6 C11 Cu1 149.9(2) . . ?
C10 C11 Cu1 74.42(15) . . ?
N2 C10 C11 113.7(3) . . ?
N2 C10 C9 114.2(3) . . ?
N2 C10 Cu1 41.83(15) . . ?
C11 C10 Cu1 71.83(15) . . ?
C9 C10 C11 132.1(3) . . ?
C9 C10 Cu1 156.0(2) . . ?
C10 C9 C8 122.4(3) . . ?
N9 N8 N7 175.0(3) . . ?
C5 C6 N2 113.7(3) . . ?
C7 C6 N2 124.3(3) . . ?
C7 C6 C5 122.0(3) . . ?
N1 C5 C6 109.1(3) . . ?
N1 C5 C4 127.2(3) . . ?
C6 C5 C4 123.7(3) . . ?
C3 C4 C5 117.0(3) . . ?
C4 C3 C2 115.9(3) . . ?
C8 C7 C6 111.2(3) . . ?
C3 C2 C1 124.6(3) . . ?
C7 C8 C9 123.1(3) . . ?
N1 C1 C2 120.0(3) . . ?
N3 Cu1 N7 98.87(11) . . ?
N3 Cu1 N1 160.65(11) . . ?
N3 Cu1 C11 27.52(10) . . ?
N3 Cu1 C10 61.25(10) . . ?
N7 Cu1 C11 123.18(10) . . ?
N7 Cu1 C10 149.83(10) . . ?
N2 Cu1 N3 87.21(12) . . ?
N2 Cu1 N7 156.26(11) . . ?
N2 Cu1 N1 73.65(10) . . ?
N2 Cu1 C11 59.73(10) . . ?
N2 Cu1 C10 25.98(10) . . ?
N1 Cu1 N7 97.66(10) . . ?
N1 Cu1 C11 133.18(10) . . ?
N1 Cu1 C10 99.54(10) . . ?
C11 Cu1 C10 33.75(10) . . ?

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
N3 C11 C10 N2 -1.7(4) . . . . ?
N3 C11 C10 C9 179.1(4) . . . . ?
N3 C11 C10 Cu1 -2.4(3) . . . . ?
N2 C10 C9 C8 -0.3(5) . . . . ?
N2 C6 C5 N1 -3.7(4) . . . . ?
N2 C6 C5 C4 176.6(3) . . . . ?
N2 C6 C7 C8 1.5(5) . . . . ?
N1 C5 C4 C3 0.5(5) . . . . ?
N6 N5 N4 N3 -0.8(3) . . . . ?
N6 C11 C10 N2 177.5(4) . . . . ?
N6 C11 C10 C9 -1.7(6) . . . . ?
N6 C11 C10 Cu1 176.8(4) . . . . ?
N5 N6 C11 N3 0.0(4) . . . . ?
N5 N6 C11 C10 -179.3(3) . . . . ?
N5 N6 C11 Cu1 -5.4(6) . . . . ?
N4 N3 C11 N6 -0.5(4) . . . . ?
N4 N3 C11 C10 178.9(3) . . . . ?
N4 N3 C11 Cu1 175.7(3) . . . . ?
N4 N3 Cu1 N7 -19.3(4) . . . . ?
N4 N3 Cu1 N2 -176.2(4) . . . . ?
N4 N3 Cu1 N1 -167.6(3) . . . . ?
N4 N3 Cu1 C11 -173.3(5) . . . . ?
N4 N3 Cu1 C10 -175.1(4) . . . . ?
C11 N3 N4 N5 0.9(4) . . . . ?
C11 N3 Cu1 N7 154.0(2) . . . . ?
C11 N3 Cu1 N2 -2.9(2) . . . . ?
C11 N3 Cu1 N1 5.7(5) . . . . ?
C11 N3 Cu1 C10 -1.79(19) . . . . ?
C11 N6 N5 N4 0.6(4) . . . . ?
C11 C10 C9 C8 178.9(3) . . . . ?
C10 N2 C6 C5 176.9(3) . . . . ?
C10 N2 C6 C7 -2.3(5) . . . . ?
C10 N2 Cu1 N3 2.2(2) . . . . ?
C10 N2 Cu1 N7 -103.7(3) . . . . ?
C10 N2 Cu1 N1 -174.9(2) . . . . ?
C10 N2 Cu1 C11 0.6(2) . . . . ?
C10 C9 C8 C7 -0.3(6) . . . . ?
C6 N2 C10 C11 -177.8(3) . . . . ?
C6 N2 C10 C9 1.5(5) . . . . ?
C6 N2 C10 Cu1 -176.8(4) . . . . ?
C6 N2 Cu1 N3 179.0(2) . . . . ?
C6 N2 Cu1 N7 73.2(3) . . . . ?
C6 N2 Cu1 N1 2.0(2) . . . . ?
C6 N2 Cu1 C11 177.5(3) . . . . ?
C6 N2 Cu1 C10 176.9(4) . . . . ?
C6 C5 C4 C3 -179.9(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C5 N1 C1 C2 1.0(4) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
C5 C4 C3 C2 0.2(5) . . . . ?
C4 C3 C2 C1 -0.2(5) . . . . ?
C3 C2 C1 N1 -0.4(5) . . . . ?
C7 C6 C5 N1 175.5(3) . . . . ?
C7 C6 C5 C4 -4.2(5) . . . . ?
C1 N1 C5 C6 179.2(3) . . . . ?
C1 N1 C5 C4 -1.1(5) . . . . ?
Cu1 N3 N4 N5 174.1(3) . . . . ?
Cu1 N3 C11 N6 -176.2(2) . . . . ?
Cu1 N3 C11 C10 3.2(3) . . . . ?
Cu1 N2 C10 C11 -1.0(3) . . . . ?
Cu1 N2 C10 C9 178.3(2) . . . . ?
Cu1 N2 C6 C5 0.4(4) . . . . ?
Cu1 N2 C6 C7 -178.8(2) . . . . ?
Cu1 N1 C5 C6 5.5(3) . . . . ?
Cu1 N1 C5 C4 -174.7(2) . . . . ?
Cu1 N1 C1 C2 174.4(2) . . . . ?
Cu1 C11 C10 N2 0.7(2) . . . . ?
Cu1 C11 C10 C9 -178.5(4) . . . . ?
Cu1 C10 C9 C8 2.4(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tjd208-22_0m
_database_code_depnum_ccdc_archive 'CCDC 1439546'
_audit_update_record             
;
2015-12-27 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
_audit_creation_date             2015-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H7 Mn N9'
_chemical_formula_sum            'C11 H7 Mn N9'
_chemical_formula_weight         320.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   8.9867(7)
_cell_length_b                   14.7912(11)
_cell_length_c                   17.9613(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2387.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9060
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1050 before and 0.0377 after correction.
The Ratio of minimum to maximum transmission is 0.8660.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             2742
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.251
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+4.2322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C2(H2), C7(H7), C1(H1), C9(H9), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.94002(4) 0.10097(2) 0.53832(2) 0.01747(10) Uani 1 1 d . . . . .
N2 N 0.7864(2) 0.17238(12) 0.61745(11) 0.0184(4) Uani 1 1 d . . . . .
N1 N 1.0003(2) 0.06167(13) 0.65958(11) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.9425(3) 0.07768(17) 0.78955(14) 0.0260(5) Uani 1 1 d . . . . .
H4 H 0.8888 0.1068 0.8267 0.031 Uiso 1 1 calc R . . . .
C5 C 0.9231(3) 0.10148(15) 0.71487(14) 0.0204(5) Uani 1 1 d . . . . .
C8 C 0.6259(3) 0.28126(16) 0.71217(14) 0.0255(5) Uani 1 1 d . . . . .
H8 H 0.5718 0.3179 0.7444 0.031 Uiso 1 1 calc R . . . .
C6 C 0.8116(3) 0.16937(15) 0.69096(13) 0.0194(4) Uani 1 1 d . . . . .
C10 C 0.6830(3) 0.22874(14) 0.59026(13) 0.0196(5) Uani 1 1 d . . . . .
C2 C 1.1219(3) -0.03053(16) 0.75088(17) 0.0305(6) Uani 1 1 d . . . . .
H2 H 1.1902 -0.0760 0.7614 0.037 Uiso 1 1 calc R . . . .
C7 C 0.7341(3) 0.22412(16) 0.74011(14) 0.0243(5) Uani 1 1 d . . . . .
H7 H 0.7544 0.2224 0.7909 0.029 Uiso 1 1 calc R . . . .
C1 C 1.0983(3) -0.00286(16) 0.67805(15) 0.0258(5) Uani 1 1 d . . . . .
H1 H 1.1530 -0.0303 0.6403 0.031 Uiso 1 1 calc R . . . .
C9 C 0.5980(3) 0.28407(16) 0.63656(14) 0.0237(5) Uani 1 1 d . . . . .
H9 H 0.5248 0.3217 0.6171 0.028 Uiso 1 1 calc R . . . .
C3 C 1.0430(3) 0.01001(18) 0.80735(16) 0.0308(6) Uani 1 1 d . . . . .
H3 H 1.0568 -0.0077 0.8566 0.037 Uiso 1 1 calc R . . . .
N6 N 1.0741(2) 0.23219(12) 0.53446(11) 0.0195(4) Uani 1 1 d . . . . .
N3 N 0.7527(2) 0.16554(13) 0.47060(11) 0.0205(4) Uani 1 1 d . . . . .
N5 N 1.0992(2) 0.26605(14) 0.60304(12) 0.0264(5) Uani 1 1 d . . . . .
N7 N 0.8606(2) -0.03527(13) 0.51047(12) 0.0228(4) Uani 1 1 d . . . . .
N4 N 1.2059(2) 0.32685(14) 0.59982(12) 0.0275(5) Uani 1 1 d . . . . .
C11 C 1.1677(3) 0.27711(14) 0.49049(14) 0.0194(5) Uani 1 1 d . . . . .
N8 N 0.7360(2) -0.06038(14) 0.49732(13) 0.0268(5) Uani 1 1 d . . . . .
N9 N 0.6186(3) -0.08614(19) 0.4839(2) 0.0549(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N2 2.2452(19) . ?
Mn1 N1 2.318(2) . ?
Mn1 N6 2.2857(19) . ?
Mn1 N3 2.286(2) . ?
Mn1 N7 2.195(2) . ?
Mn1 N7 2.219(2) 5_756 ?
N2 C6 1.340(3) . ?
N2 C10 1.341(3) . ?
N1 C5 1.347(3) . ?
N1 C1 1.341(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C4 C3 1.385(4) . ?
C5 C6 1.483(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.382(4) . ?
C8 C9 1.382(4) . ?
C6 C7 1.386(3) . ?
C10 C9 1.394(3) . ?
C10 C11 1.460(3) 4_456 ?
C2 H2 0.9300 . ?
C2 C1 1.387(4) . ?
C2 C3 1.375(4) . ?
C7 H7 0.9300 . ?
C1 H1 0.9300 . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
N6 N5 1.349(3) . ?
N6 C11 1.331(3) . ?
N3 N4 1.338(3) 4_456 ?
N3 C11 1.338(3) 4_456 ?
N5 N4 1.316(3) . ?
N7 Mn1 2.219(2) 5_756 ?
N7 N8 1.203(3) . ?
N4 N3 1.337(3) 4_556 ?
C11 C10 1.459(3) 4_556 ?
C11 N3 1.338(3) 4_556 ?
N8 N9 1.147(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Mn1 N1 70.54(7) . . ?
N2 Mn1 N6 86.78(7) . . ?
N2 Mn1 N3 71.79(7) . . ?
N6 Mn1 N1 96.78(7) . . ?
N6 Mn1 N3 91.00(7) . . ?
N3 Mn1 N1 140.96(7) . . ?
N7 Mn1 N2 162.28(8) 5_756 . ?
N7 Mn1 N2 112.10(7) . . ?
N7 Mn1 N1 94.16(8) 5_756 . ?
N7 Mn1 N1 93.43(7) . . ?
N7 Mn1 N6 160.71(8) . . ?
N7 Mn1 N6 86.23(7) 5_756 . ?
N7 Mn1 N3 91.31(7) . . ?
N7 Mn1 N3 124.58(8) 5_756 . ?
N7 Mn1 N7 76.73(8) . 5_756 ?
C6 N2 Mn1 120.28(15) . . ?
C6 N2 C10 119.8(2) . . ?
C10 N2 Mn1 119.23(16) . . ?
C5 N1 Mn1 117.57(15) . . ?
C1 N1 Mn1 124.37(17) . . ?
C1 N1 C5 117.8(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
N1 C5 C4 122.2(2) . . ?
N1 C5 C6 115.5(2) . . ?
C4 C5 C6 122.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
N2 C6 C5 115.0(2) . . ?
N2 C6 C7 121.6(2) . . ?
C7 C6 C5 123.4(2) . . ?
N2 C10 C9 121.8(2) . . ?
N2 C10 C11 113.0(2) . 4_456 ?
C9 C10 C11 125.2(2) . 4_456 ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.2(2) . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C1 C2 122.9(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C8 C9 C10 118.0(2) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.6 . . ?
N5 N6 Mn1 112.07(14) . . ?
C11 N6 Mn1 140.79(16) . . ?
C11 N6 N5 104.52(19) . . ?
N4 N3 Mn1 140.33(15) 4_456 . ?
N4 N3 C11 105.13(19) 4_456 4_456 ?
C11 N3 Mn1 114.03(15) 4_456 . ?
N4 N5 N6 109.6(2) . . ?
Mn1 N7 Mn1 103.27(8) . 5_756 ?
N8 N7 Mn1 122.59(16) . 5_756 ?
N8 N7 Mn1 129.10(16) . . ?
N5 N4 N3 109.2(2) . 4_556 ?
N6 C11 C10 128.3(2) . 4_556 ?
N6 C11 N3 111.5(2) . 4_556 ?
N3 C11 C10 120.2(2) 4_556 4_556 ?
N9 N8 N7 178.3(3) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tjd053_0m
_database_code_depnum_ccdc_archive 'CCDC 1439547'
_audit_update_record             
;
2015-12-27 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
_audit_creation_date             2015-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H7 Co N9'
_chemical_formula_sum            'C11 H7 Co N9'
_chemical_formula_weight         324.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.7778(8)
_cell_length_b                   12.1999(9)
_cell_length_c                   9.5936(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.4630(10)
_cell_angle_gamma                90
_cell_volume                     1181.84(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4846
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.461
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0391 before and 0.0310 after correction.
The Ratio of minimum to maximum transmission is 0.9382.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9074
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_min         2.017
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2670
_reflns_number_total             2945
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²+0.6767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0596
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1), C7(H7), C2(H2), C8(H8), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.37612(2) 0.57823(2) 0.51305(2) 0.01074(7) Uani 1 1 d . . . . .
N1 N 0.30655(12) 0.45466(10) 0.62888(13) 0.0141(2) Uani 1 1 d . . . . .
N7 N 0.57258(12) 0.55692(10) 0.62445(13) 0.0144(2) Uani 1 1 d . . . . .
N2 N 0.18169(12) 0.54712(9) 0.37474(13) 0.0117(2) Uani 1 1 d . . . . .
N8 N 0.63709(12) 0.56360(10) 0.75526(14) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.00772(14) 0.57429(12) 0.14160(16) 0.0157(3) Uani 1 1 d . . . . .
H9 H -0.0274 0.6129 0.0528 0.019 Uiso 1 1 calc R . . . .
C5 C 0.18561(14) 0.41177(11) 0.55397(16) 0.0132(3) Uani 1 1 d . . . . .
N9 N 0.70323(15) 0.56726(12) 0.87856(15) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.37574(16) 0.41300(12) 0.76284(17) 0.0185(3) Uani 1 1 d . . . . .
H1 H 0.4582 0.4430 0.8154 0.022 Uiso 1 1 calc R . . . .
C7 C -0.00954(15) 0.43350(12) 0.30962(17) 0.0164(3) Uani 1 1 d . . . . .
H7 H -0.0556 0.3761 0.3330 0.020 Uiso 1 1 calc R . . . .
C6 C 0.11444(14) 0.46510(11) 0.40795(15) 0.0124(3) Uani 1 1 d . . . . .
C2 C 0.33023(16) 0.32739(13) 0.82677(17) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.3808 0.3004 0.9200 0.025 Uiso 1 1 calc R . . . .
C8 C -0.06279(14) 0.48964(13) 0.17600(16) 0.0173(3) Uani 1 1 d . . . . .
H8 H -0.1459 0.4705 0.1094 0.021 Uiso 1 1 calc R . . . .
C10 C 0.13200(14) 0.59974(11) 0.24329(15) 0.0127(3) Uani 1 1 d . . . . .
C3 C 0.20788(17) 0.28333(13) 0.74840(18) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.1752 0.2252 0.7880 0.026 Uiso 1 1 calc R . . . .
C4 C 0.13343(16) 0.32597(12) 0.60999(17) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.0504 0.2974 0.5563 0.022 Uiso 1 1 calc R . . . .
N3 N 0.34540(12) 0.69120(10) 0.33139(13) 0.0137(2) Uani 1 1 d . . . . .
C11 C 0.22603(14) 0.67988(11) 0.22352(15) 0.0126(3) Uani 1 1 d . . . . .
N5 N 0.33099(12) 0.79868(10) 0.14824(13) 0.0140(2) Uani 1 1 d . . . . .
N4 N 0.41000(12) 0.76733(10) 0.28218(13) 0.0148(2) Uani 1 1 d . . . . .
N6 N 0.21309(12) 0.74509(10) 0.10783(13) 0.0147(2) 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 N1 2.1569(12) . ?
Co1 N7 2.2966(12) 3_666 ?
Co1 N7 2.0276(12) . ?
Co1 N2 2.0861(12) . ?
Co1 N3 2.1548(12) . ?
Co1 N5 2.1482(12) 4_576 ?
N1 C5 1.3544(19) . ?
N1 C1 1.3401(19) . ?
N7 Co1 2.2966(12) 3_666 ?
N7 N8 1.2062(17) . ?
N2 C6 1.3377(18) . ?
N2 C10 1.3480(18) . ?
N8 N9 1.1488(18) . ?
C9 H9 0.9300 . ?
C9 C8 1.389(2) . ?
C9 C10 1.389(2) . ?
C5 C6 1.4909(19) . ?
C5 C4 1.383(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.394(2) . ?
C7 C8 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(2) . ?
C8 H8 0.9300 . ?
C10 C11 1.467(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9300 . ?
N3 C11 1.3469(18) . ?
N3 N4 1.3417(16) . ?
C11 N6 1.3326(18) . ?
N5 Co1 2.1483(12) 4_575 ?
N5 N4 1.3256(16) . ?
N5 N6 1.3594(17) . ?

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 N7 89.49(5) . 3_666 ?
N7 Co1 N1 97.23(5) . . ?
N7 Co1 N7 78.11(5) . 3_666 ?
N7 Co1 N2 160.68(5) . . ?
N7 Co1 N3 110.19(5) . . ?
N7 Co1 N5 100.75(5) . 4_576 ?
N2 Co1 N1 75.39(5) . . ?
N2 Co1 N7 83.92(4) . 3_666 ?
N2 Co1 N3 76.45(5) . . ?
N2 Co1 N5 97.01(5) . 4_576 ?
N3 Co1 N1 151.76(5) . . ?
N3 Co1 N7 89.68(4) . 3_666 ?
N5 Co1 N1 89.12(5) 4_576 . ?
N5 Co1 N7 178.07(4) 4_576 3_666 ?
N5 Co1 N3 92.18(5) 4_576 . ?
C5 N1 Co1 116.11(9) . . ?
C1 N1 Co1 125.59(10) . . ?
C1 N1 C5 118.16(13) . . ?
Co1 N7 Co1 101.89(5) . 3_666 ?
N8 N7 Co1 118.63(10) . 3_666 ?
N8 N7 Co1 130.97(10) . . ?
C6 N2 Co1 119.47(9) . . ?
C6 N2 C10 120.53(12) . . ?
C10 N2 Co1 119.38(9) . . ?
N9 N8 N7 176.75(16) . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.22(13) . . ?
C10 C9 H9 120.9 . . ?
N1 C5 C6 114.43(12) . . ?
N1 C5 C4 122.21(13) . . ?
C4 C5 C6 123.37(13) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.11(15) . . ?
C2 C1 H1 118.4 . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C8 C7 C6 118.52(14) . . ?
N2 C6 C5 113.99(12) . . ?
N2 C6 C7 121.11(13) . . ?
C7 C6 C5 124.87(13) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.16(14) . . ?
C3 C2 H2 120.9 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.16(13) . . ?
C7 C8 H8 119.9 . . ?
N2 C10 C9 121.39(13) . . ?
N2 C10 C11 111.83(12) . . ?
C9 C10 C11 126.75(13) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.85(15) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.50(15) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C11 N3 Co1 113.03(9) . . ?
N4 N3 Co1 140.85(9) . . ?
N4 N3 C11 105.93(11) . . ?
N3 C11 C10 119.10(12) . . ?
N6 C11 C10 129.01(13) . . ?
N6 C11 N3 111.87(12) . . ?
N4 N5 Co1 125.63(9) . 4_575 ?
N4 N5 N6 110.94(11) . . ?
N6 N5 Co1 123.39(9) . 4_575 ?
N5 N4 N3 107.71(11) . . ?
C11 N6 N5 103.55(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N1 C5 C6 -5.54(15) . . . . ?
Co1 N1 C5 C4 174.77(11) . . . . ?
Co1 N1 C1 C2 -174.57(11) . . . . ?
Co1 N2 C6 C5 6.19(16) . . . . ?
Co1 N2 C6 C7 -172.37(10) . . . . ?
Co1 N2 C10 C9 173.92(10) . . . . ?
Co1 N2 C10 C11 -3.97(15) . . . . ?
Co1 N3 C11 C10 2.78(16) . . . . ?
Co1 N3 C11 N6 -175.53(9) . . . . ?
Co1 N3 N4 N5 173.47(11) . . . . ?
Co1 N5 N4 N3 178.49(9) 4_575 . . . ?
Co1 N5 N6 C11 -178.23(9) 4_575 . . . ?
N1 C5 C6 N2 -0.17(18) . . . . ?
N1 C5 C6 C7 178.32(13) . . . . ?
N1 C5 C4 C3 0.5(2) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
N2 C10 C11 N3 0.59(18) . . . . ?
N2 C10 C11 N6 178.57(14) . . . . ?
C9 C10 C11 N3 -177.16(14) . . . . ?
C9 C10 C11 N6 0.8(2) . . . . ?
C5 N1 C1 C2 1.0(2) . . . . ?
C1 N1 C5 C6 178.46(12) . . . . ?
C1 N1 C5 C4 -1.2(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C6 N2 C10 C9 3.0(2) . . . . ?
C6 N2 C10 C11 -174.89(12) . . . . ?
C6 C5 C4 C3 -179.20(13) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C8 C9 C10 N2 -2.6(2) . . . . ?
C8 C9 C10 C11 175.01(13) . . . . ?
C8 C7 C6 N2 -0.5(2) . . . . ?
C8 C7 C6 C5 -178.84(13) . . . . ?
C10 N2 C6 C5 177.10(12) . . . . ?
C10 N2 C6 C7 -1.5(2) . . . . ?
C10 C9 C8 C7 0.6(2) . . . . ?
C10 C11 N6 N5 -178.15(14) . . . . ?
C4 C5 C6 N2 179.51(13) . . . . ?
C4 C5 C6 C7 -2.0(2) . . . . ?
N3 C11 N6 N5 -0.06(15) . . . . ?
C11 N3 N4 N5 -0.73(15) . . . . ?
N4 N3 C11 C10 178.80(12) . . . . ?
N4 N3 C11 N6 0.50(16) . . . . ?
N4 N5 N6 C11 -0.42(15) . . . . ?
N6 N5 N4 N3 0.74(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
