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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_2016ncs0097
_database_code_depnum_ccdc_archive 'CCDC 1898421'
loop_
_audit_author_name
_audit_author_address
'Peter N. Horton'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-14
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 Co N4 O2, 2(N O3)'
_chemical_formula_sum            'C18 H24 Co N6 O8'
_chemical_formula_weight         511.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H20 Co N6 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.6698(4)
_cell_length_b                   10.05059(18)
_cell_length_c                   16.0714(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.734(3)
_cell_angle_gamma                90
_cell_volume                     2116.27(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5320
_cell_measurement_theta_min      2.5400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13100
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.110
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   1.00    5.00    --  -13.00   0.00  60.00  180
  2  ω    -74.00  23.00   1.00    5.00    --  -13.00 -72.00-180.00   97
  3  ω    -60.00  23.00   1.00    5.00    --  -13.00 -72.00   0.00   83
  4  ω    -22.00   5.00   1.00    5.00    --  -13.00  54.00 -60.00   27
  5  ω    -63.00 -43.00   1.00    5.00    --  -13.00  18.00-150.00   20
  6  ω   -103.00 -26.00   1.00    5.00    --  -13.00   0.00 -60.00   77
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0327674000
_diffrn_orient_matrix_UB_12      0.0117084000
_diffrn_orient_matrix_UB_13      -0.0478145000
_diffrn_orient_matrix_UB_21      0.0313231000
_diffrn_orient_matrix_UB_22      -0.0409557000
_diffrn_orient_matrix_UB_23      -0.0124392000
_diffrn_orient_matrix_UB_31      -0.0295844000
_diffrn_orient_matrix_UB_32      -0.0562754000
_diffrn_orient_matrix_UB_33      -0.0008631000
_diffrn_radiation_collimation    'confocal mirrors'
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2336
_reflns_number_total             2431
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0224
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+1.6210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0592
_refine_special_details          
'The ligand is disordered over the 2-fold rotation, requiring the use of PART -1 and displacement constraints (EADP) applied to the overlapping pyridine rings.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N4)
Uanis(C1) = Uanis(C18)
Uanis(C2) = Uanis(C17)
Uanis(C3) = Uanis(C16)
Uanis(C4) = Uanis(C15)
Uanis(C5) = Uanis(C14)
3. Others
 Fixed Sof: N1(0.5) N2(0.5) N3(0.5) N4(0.5) C1(0.5) H1(0.5) C2(0.5) H2(0.5)
 C3(0.5) H3(0.5) C4(0.5) H4(0.5) C5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5)
 C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9(0.5) C10(0.5) H10A(0.5) H10B(0.5)
 C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5) C13(0.5) H13(0.5)
 C14(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5) C18(0.5)
 H18(0.5)
4.a Rotating group:
 O1(H1A,H1B)
4.b Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
4.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.5000 0.73458(2) 0.2500 0.02175(8) Uani 1 2 d S T P . .
O1 O 0.35155(7) 0.71410(9) 0.23391(6) 0.0287(2) Uani 1 1 d . . . . .
H1A H 0.3333 0.7422 0.2767 0.043 Uiso 1 1 d GR . . . .
H1B H 0.3076 0.6520 0.1998 0.043 Uiso 1 1 d GR . . . .
N1 N 0.5604(10) 0.6155(3) 0.3717(9) 0.0148(12) Uani 0.5 1 d . . . A -1
N2 N 0.5619(2) 0.8792(3) 0.3574(2) 0.0182(6) Uani 0.5 1 d . . . A -1
N3 N 0.4791(2) 0.8821(3) 0.1502(2) 0.0176(5) Uani 0.5 1 d . . . A -1
N4 N 0.4527(10) 0.6189(3) 0.1214(9) 0.0148(12) Uani 0.5 1 d . . . A -1
C1 C 0.5550(12) 0.4834(7) 0.3818(10) 0.0215(9) Uani 0.5 1 d . . . A -1
H1 H 0.5192 0.4314 0.3273 0.026 Uiso 0.5 1 calc R . . A -1
C2 C 0.5971(6) 0.4201(7) 0.4646(7) 0.0198(9) Uani 0.5 1 d . . . A -1
H2 H 0.6008 0.3257 0.4688 0.024 Uiso 0.5 1 calc R . . A -1
C3 C 0.6418(3) 0.5144(13) 0.5576(8) 0.0225(4) Uani 0.5 1 d . . . A -1
H3 H 0.6638 0.4801 0.6188 0.027 Uiso 0.5 1 calc R . . A -1
C4 C 0.6442(9) 0.6316(12) 0.5416(3) 0.0236(7) Uani 0.5 1 d . . . A -1
H4 H 0.6767 0.6892 0.5936 0.028 Uiso 0.5 1 calc R . . A -1
C5 C 0.6038(4) 0.6892(4) 0.4539(5) 0.0167(8) Uani 0.5 1 d . . . A -1
C6 C 0.6031(3) 0.8327(4) 0.4393(2) 0.0235(7) Uani 0.5 1 d . . . A -1
H6 H 0.6334 0.8910 0.4912 0.028 Uiso 0.5 1 calc R . . A -1
C7 C 0.5699(2) 1.0244(3) 0.34485(16) 0.0219(5) Uani 0.5 1 d . . . A -1
H7 H 0.6281 1.0606 0.4021 0.026 Uiso 0.5 1 calc R . . A -1
C8 C 0.5920(4) 1.0481(8) 0.2616(6) 0.0243(11) Uani 0.5 1 d . . . A -1
H8A H 0.6167 1.1405 0.2647 0.029 Uiso 0.5 1 calc R . . A -1
H8B H 0.6478 0.9878 0.2671 0.029 Uiso 0.5 1 calc R . . A -1
C9 C 0.5015(2) 1.0269(3) 0.16677(17) 0.0215(5) Uani 0.5 1 d . . . A -1
H9 H 0.5196 1.0618 0.1179 0.026 Uiso 0.5 1 calc R . . A -1
C10 C 0.4076(2) 1.1011(3) 0.15937(18) 0.0251(5) Uani 0.5 1 d . . . A -1
H10A H 0.4201 1.1980 0.1608 0.030 Uiso 0.5 1 calc R . . A -1
H10B H 0.3488 1.0796 0.0990 0.030 Uiso 0.5 1 calc R . . A -1
C11 C 0.3816(4) 1.0649(7) 0.2381(5) 0.0199(9) Uani 0.5 1 d . . . A -1
H11A H 0.3636 0.9693 0.2339 0.024 Uiso 0.5 1 calc R . . A -1
H11B H 0.3217 1.1172 0.2320 0.024 Uiso 0.5 1 calc R . . A -1
C12 C 0.4723(2) 1.0934(3) 0.33242(18) 0.0257(5) Uani 0.5 1 d . . . A -1
H12A H 0.4842 1.1906 0.3391 0.031 Uiso 0.5 1 calc R . . A -1
H12B H 0.4552 1.0639 0.3825 0.031 Uiso 0.5 1 calc R . . A -1
C13 C 0.4392(3) 0.8419(3) 0.0669(2) 0.0217(7) Uani 0.5 1 d . . . A -1
H13 H 0.4212 0.9031 0.0169 0.026 Uiso 0.5 1 calc R . . A -1
C14 C 0.4210(4) 0.6982(4) 0.0488(5) 0.0167(8) Uani 0.5 1 d . . . A -1
C15 C 0.3729(9) 0.6504(11) -0.0418(3) 0.0236(7) Uani 0.5 1 d . . . A -1
H15 H 0.3510 0.7054 -0.0955 0.028 Uiso 0.5 1 calc R . . A -1
C16 C 0.3586(3) 0.4935(12) -0.0459(7) 0.0225(4) Uani 0.5 1 d . . . A -1
H16 H 0.3223 0.4517 -0.1048 0.027 Uiso 0.5 1 calc R . . A -1
C17 C 0.3893(6) 0.4321(7) 0.0170(7) 0.0198(9) Uani 0.5 1 d . . . A -1
H17 H 0.3856 0.3380 0.0106 0.024 Uiso 0.5 1 calc R . . A -1
C18 C 0.4352(12) 0.4886(7) 0.1089(11) 0.0215(9) Uani 0.5 1 d . . . A -1
H18 H 0.4532 0.4323 0.1615 0.026 Uiso 0.5 1 calc R . . A -1
O21 O 0.31918(7) 0.38654(10) 0.23578(6) 0.0320(2) Uani 1 1 d . . . . .
O22 O 0.22849(8) 0.51976(10) 0.12340(7) 0.0359(2) Uani 1 1 d . . . . .
O23 O 0.17853(8) 0.31707(11) 0.12151(7) 0.0393(3) Uani 1 1 d . . . . .
N21 N 0.24290(8) 0.40685(11) 0.16057(7) 0.0257(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 O1 2.0845(10) . ?
Co1 O1 2.0846(10) 2_655 ?
Co1 N1 2.118(11) . ?
Co1 N2 2.123(3) . ?
Co1 N3 2.103(3) . ?
Co1 N4 2.194(11) . ?
O1 H1A 0.8877 . ?
O1 H1B 0.8875 . ?
N1 C1 1.345(9) . ?
N1 C5 1.394(12) . ?
N2 C6 1.265(5) . ?
N2 C7 1.485(4) . ?
N3 C9 1.489(4) . ?
N3 C13 1.262(5) . ?
N4 C14 1.312(12) . ?
N4 C18 1.333(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.349(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.637(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.21(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(9) . ?
C5 C6 1.460(5) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.531(7) . ?
C7 C12 1.521(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.520(8) . ?
C9 H9 1.0000 . ?
C9 C10 1.523(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.529(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C14 1.474(5) . ?
C14 C15 1.388(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.589(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.093(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.437(19) . ?
C18 H18 0.9500 . ?
O21 N21 1.2401(14) . ?
O22 N21 1.2553(14) . ?
O23 N21 1.2517(14) . ?

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 O1 168.67(5) . 2_655 ?
O1 Co1 N1 81.4(3) 2_655 . ?
O1 Co1 N1 92.2(3) . . ?
O1 Co1 N2 85.73(7) 2_655 . ?
O1 Co1 N2 102.11(7) . . ?
O1 Co1 N3 87.12(7) 2_655 . ?
O1 Co1 N3 100.92(7) . . ?
O1 Co1 N4 87.8(3) . . ?
O1 Co1 N4 86.2(3) 2_655 . ?
N1 Co1 N2 77.7(2) . . ?
N1 Co1 N4 113.24(9) . . ?
N2 Co1 N4 165.2(2) . . ?
N3 Co1 N1 163.7(3) . . ?
N3 Co1 N2 89.98(7) . . ?
N3 Co1 N4 77.23(19) . . ?
Co1 O1 H1A 122.3 . . ?
Co1 O1 H1B 125.0 . . ?
H1A O1 H1B 108.2 . . ?
C1 N1 Co1 130.3(10) . . ?
C1 N1 C5 115.9(11) . . ?
C5 N1 Co1 113.4(3) . . ?
C6 N2 Co1 115.0(2) . . ?
C6 N2 C7 118.3(3) . . ?
C7 N2 Co1 126.4(2) . . ?
C9 N3 Co1 127.4(2) . . ?
C13 N3 Co1 115.0(2) . . ?
C13 N3 C9 117.5(3) . . ?
C14 N4 Co1 110.6(4) . . ?
C14 N4 C18 119.7(11) . . ?
C18 N4 Co1 128.3(9) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.0(10) . . ?
C2 C1 H1 118.0 . . ?
C1 C2 H2 121.8 . . ?
C1 C2 C3 116.4(8) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 H3 123.0 . . ?
C4 C3 C2 114.0(11) . . ?
C4 C3 H3 123.0 . . ?
C3 C4 H4 117.2 . . ?
C3 C4 C5 125.7(8) . . ?
C5 C4 H4 117.2 . . ?
N1 C5 C6 113.9(6) . . ?
C4 C5 N1 123.1(6) . . ?
C4 C5 C6 123.0(6) . . ?
N2 C6 C5 119.8(4) . . ?
N2 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N2 C7 H7 108.6 . . ?
N2 C7 C8 109.4(4) . . ?
N2 C7 C12 109.8(2) . . ?
C8 C7 H7 108.6 . . ?
C12 C7 H7 108.6 . . ?
C12 C7 C8 111.8(4) . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 114.9(3) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
N3 C9 C8 109.9(4) . . ?
N3 C9 H9 108.5 . . ?
N3 C9 C10 110.2(3) . . ?
C8 C9 H9 108.5 . . ?
C8 C9 C10 111.2(4) . . ?
C10 C9 H9 108.5 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 112.0(3) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C10 C11 C12 110.4(4) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C7 C12 C11 113.1(3) . . ?
C7 C12 H12A 108.9 . . ?
C7 C12 H12B 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 H13 120.7 . . ?
N3 C13 C14 118.6(4) . . ?
C14 C13 H13 120.7 . . ?
N4 C14 C13 117.3(6) . . ?
N4 C14 C15 122.2(6) . . ?
C15 C14 C13 120.5(6) . . ?
C14 C15 H15 123.8 . . ?
C14 C15 C16 112.5(6) . . ?
C16 C15 H15 123.8 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(13) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 118.8 . . ?
C16 C17 C18 122.3(11) . . ?
C18 C17 H17 118.8 . . ?
N4 C18 C17 120.9(9) . . ?
N4 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
O21 N21 O22 119.84(11) . . ?
O21 N21 O23 121.11(11) . . ?
O23 N21 O22 119.04(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O23 0.89 1.88 2.7545(13) 168.3 4
O1 H1B O22 0.89 1.83 2.7100(14) 172.6 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N1 C1 C2 -179.7(9) . . . . ?
Co1 N1 C5 C4 177.4(7) . . . . ?
Co1 N1 C5 C6 -2.6(9) . . . . ?
Co1 N2 C6 C5 -0.8(5) . . . . ?
Co1 N2 C7 C8 -35.3(4) . . . . ?
Co1 N2 C7 C12 87.8(2) . . . . ?
Co1 N3 C9 C8 32.0(4) . . . . ?
Co1 N3 C9 C10 -90.8(2) . . . . ?
Co1 N3 C13 C14 -5.8(4) . . . . ?
Co1 N4 C14 C13 10.3(9) . . . . ?
Co1 N4 C14 C15 -170.3(8) . . . . ?
Co1 N4 C18 C17 170.2(8) . . . . ?
N1 C1 C2 C3 9.6(16) . . . . ?
N1 C5 C6 N2 2.4(8) . . . . ?
N2 C7 C8 C9 74.5(6) . . . . ?
N2 C7 C12 C11 -71.9(4) . . . . ?
N3 C9 C10 C11 67.6(4) . . . . ?
N3 C13 C14 N4 -3.6(9) . . . . ?
N3 C13 C14 C15 177.0(8) . . . . ?
N4 C14 C15 C16 1.8(15) . . . . ?
C1 N1 C5 C4 3.2(15) . . . . ?
C1 N1 C5 C6 -176.9(9) . . . . ?
C1 C2 C3 C4 -9.5(12) . . . . ?
C2 C3 C4 C5 7.0(15) . . . . ?
C3 C4 C5 N1 -4.4(17) . . . . ?
C3 C4 C5 C6 175.6(9) . . . . ?
C4 C5 C6 N2 -177.7(7) . . . . ?
C5 N1 C1 C2 -6.6(18) . . . . ?
C6 N2 C7 C8 138.3(4) . . . . ?
C6 N2 C7 C12 -98.6(3) . . . . ?
C7 N2 C6 C5 -175.1(3) . . . . ?
C7 C8 C9 N3 -72.6(6) . . . . ?
C7 C8 C9 C10 49.7(6) . . . . ?
C8 C7 C12 C11 49.7(6) . . . . ?
C8 C9 C10 C11 -54.5(6) . . . . ?
C9 N3 C13 C14 177.0(3) . . . . ?
C9 C10 C11 C12 57.3(4) . . . . ?
C10 C11 C12 C7 -55.1(5) . . . . ?
C12 C7 C8 C9 -47.3(6) . . . . ?
C13 N3 C9 C8 -151.2(4) . . . . ?
C13 N3 C9 C10 86.0(3) . . . . ?
C13 C14 C15 C16 -178.7(7) . . . . ?
C14 N4 C18 C17 5.1(18) . . . . ?
C14 C15 C16 C17 -4.3(16) . . . . ?
C15 C16 C17 C18 7.0(15) . . . . ?
C16 C17 C18 N4 -7.8(17) . . . . ?
C18 N4 C14 C13 177.8(9) . . . . ?
C18 N4 C14 C15 -2.8(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-09
_olex2_date_sample_submission    2016-02-16
_olex2_submission_original_sample_id BH1-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.766
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1898426'
loop_
_audit_author_name
_audit_author_address
'Hani El Moll'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-06-11 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_structural     ?
_chemical_formula_moiety         'C18 H20 Co N5 O4, N O3'
_chemical_formula_sum            'C18 H20 Co N6 O7'
_chemical_formula_weight         491.33

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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.7738(10)
_cell_length_b                   18.751(2)
_cell_length_c                   12.1853(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.493(12)
_cell_angle_gamma                90
_cell_volume                     1964.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    10352
_cell_measurement_theta_min      3.3980
_cell_measurement_theta_max      29.8230

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.931
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      140(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.0050
_diffrn_reflns_number            30991
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.184
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4507
_reflns_number_gt                3962
_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0375P)²+1.0105P] 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         4507
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.00365(2) 0.29246(2) 0.82907(2) 0.01528(7) Uani 1 1 d . . . . .
C1 C 0.2533(2) 0.18739(9) 0.78355(16) 0.0225(4) Uani 1 1 d . . . . .
H1 H 0.2684 0.1388 0.7536 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3320(2) 0.24067(10) 0.71993(17) 0.0259(4) Uani 1 1 d . . . . .
H2A H 0.2743 0.2429 0.6414 0.031 Uiso 1 1 calc R U . . .
H2B H 0.4387 0.2239 0.7190 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3408(2) 0.31551(10) 0.77032(16) 0.0240(4) Uani 1 1 d . . . . .
H3 H 0.4011 0.3472 0.7285 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4229(2) 0.31256(10) 0.89428(17) 0.0260(4) Uani 1 1 d . . . . .
H4A H 0.5322 0.2976 0.8991 0.031 Uiso 1 1 calc R U . . .
H4B H 0.4238 0.3609 0.9270 0.031 Uiso 1 1 calc R U . . .
C5 C 0.34384(19) 0.26102(9) 0.96280(16) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.4078 0.2570 1.0402 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3229(2) 0.18718(9) 0.90914(16) 0.0230(4) Uani 1 1 d . . . . .
H6A H 0.2546 0.1586 0.9478 0.028 Uiso 1 1 calc R U . . .
H6B H 0.4254 0.1632 0.9212 0.028 Uiso 1 1 calc R U . . .
C7 C 0.1811(2) 0.33116(9) 1.05167(15) 0.0222(4) Uani 1 1 d . . . . .
H7 H 0.2626 0.3328 1.1160 0.027 Uiso 1 1 calc R U . . .
C8 C 0.0383(2) 0.37292(9) 1.04594(14) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.0186(2) 0.41658(10) 1.13323(16) 0.0267(4) Uani 1 1 d . . . . .
H9 H 0.0955 0.4194 1.2001 0.032 Uiso 1 1 calc R U . . .
C10 C -0.1178(2) 0.45627(10) 1.11992(16) 0.0287(4) Uani 1 1 d . . . . .
H10 H -0.1357 0.4867 1.1784 0.034 Uiso 1 1 calc R U . . .
C11 C -0.2277(2) 0.45134(10) 1.02115(16) 0.0265(4) Uani 1 1 d . . . . .
H11 H -0.3213 0.4782 1.0111 0.032 Uiso 1 1 calc R U . . .
C12 C -0.1983(2) 0.40643(9) 0.93745(15) 0.0223(4) Uani 1 1 d . . . . .
H12 H -0.2737 0.4029 0.8699 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1335(2) 0.39376(9) 0.69035(15) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.2052 0.4208 0.6584 0.025 Uiso 1 1 calc R U . . .
C14 C -0.0341(2) 0.41089(9) 0.66570(14) 0.0201(3) Uani 1 1 d . . . . .
C15 C -0.0961(2) 0.47276(9) 0.61232(15) 0.0249(4) Uani 1 1 d . . . . .
H15 H -0.0294 0.5086 0.5933 0.030 Uiso 1 1 calc R U . . .
C16 C -0.2571(2) 0.48195(10) 0.58676(15) 0.0277(4) Uani 1 1 d . . . . .
H16 H -0.3014 0.5247 0.5525 0.033 Uiso 1 1 calc R U . . .
C17 C -0.3505(2) 0.42796(10) 0.61208(15) 0.0254(4) Uani 1 1 d . . . . .
H17 H -0.4605 0.4315 0.5918 0.030 Uiso 1 1 calc R U . . .
C18 C -0.2804(2) 0.36803(10) 0.66814(14) 0.0215(4) Uani 1 1 d . . . . .
H18 H -0.3450 0.3311 0.6864 0.026 Uiso 1 1 calc R U . . .
O1 O 0.08645(14) 0.20234(6) 0.76134(11) 0.0202(3) Uani 1 1 d . . . . .
O2 O -0.20678(14) 0.23537(7) 0.81957(11) 0.0238(3) Uani 1 1 d . . . . .
O3 O -0.07713(17) 0.19111(9) 0.97578(13) 0.0392(4) Uani 1 1 d . . . . .
O4 O -0.30844(16) 0.15143(8) 0.90277(15) 0.0401(4) Uani 1 1 d . . . . .
O5 O -0.05503(19) 0.07720(8) 0.71095(18) 0.0562(5) Uani 1 1 d . . . . .
O6 O 0.13859(17) 0.03296(7) 0.83043(12) 0.0348(3) Uani 1 1 d . . . . .
O7 O 0.03047(18) -0.02750(7) 0.68455(12) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.17916(16) 0.34190(7) 0.75539(12) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.19197(16) 0.29283(7) 0.96793(12) 0.0189(3) Uani 1 1 d . . . . .
N3 N -0.12518(16) 0.36017(7) 0.69761(11) 0.0180(3) Uani 1 1 d . . . . .
N4 N -0.06809(16) 0.36790(7) 0.94808(12) 0.0179(3) Uani 1 1 d . . . . .
N5 N -0.19738(17) 0.19128(8) 0.90147(13) 0.0227(3) Uani 1 1 d . . . . .
N6 N 0.03811(17) 0.02724(8) 0.74161(14) 0.0247(3) Uani 1 1 d . . . . .
H01 H 0.036(3) 0.1641(15) 0.759(2) 0.053(8) Uiso 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 2.0746(12) . ?
Co1 N2 2.1163(15) . ?
Co1 O2 2.1174(13) . ?
Co1 N1 2.1419(14) . ?
Co1 N3 2.1758(14) . ?
Co1 N4 2.2054(14) . ?
C1 O1 1.462(2) . ?
C1 C2 1.513(2) . ?
C1 C6 1.530(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.479(2) . ?
C3 C4 1.539(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.531(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.473(2) . ?
C5 C6 1.527(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.267(2) . ?
C7 C8 1.467(2) . ?
C7 H7 0.9500 . ?
C8 N4 1.363(2) . ?
C8 C9 1.380(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 N4 1.336(2) . ?
C12 H12 0.9500 . ?
C13 N1 1.268(2) . ?
C13 C14 1.477(2) . ?
C13 H13 0.9500 . ?
C14 N3 1.348(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 N3 1.345(2) . ?
C18 H18 0.9500 . ?
O1 H01 0.84(3) . ?
O2 N5 1.286(2) . ?
O3 N5 1.246(2) . ?
O4 N5 1.231(2) . ?
O5 N6 1.250(2) . ?
O6 N6 1.257(2) . ?
O7 N6 1.234(2) . ?

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 N2 92.36(5) . . ?
O1 Co1 O2 86.39(5) . . ?
N2 Co1 O2 125.36(5) . . ?
O1 Co1 N1 81.25(5) . . ?
N2 Co1 N1 79.73(6) . . ?
O2 Co1 N1 152.60(5) . . ?
O1 Co1 N3 110.74(5) . . ?
N2 Co1 N3 142.66(5) . . ?
O2 Co1 N3 86.29(5) . . ?
N1 Co1 N3 75.54(5) . . ?
O1 Co1 N4 162.27(5) . . ?
N2 Co1 N4 75.63(5) . . ?
O2 Co1 N4 90.01(5) . . ?
N1 Co1 N4 108.74(5) . . ?
N3 Co1 N4 86.30(5) . . ?
O1 C1 C2 108.72(14) . . ?
O1 C1 C6 111.76(14) . . ?
C2 C1 C6 112.47(15) . . ?
O1 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
C6 C1 H1 107.9 . . ?
C1 C2 C3 113.10(15) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C2 106.73(14) . . ?
N1 C3 C4 112.49(15) . . ?
C2 C3 C4 109.73(15) . . ?
N1 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C5 C4 C3 112.55(14) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N2 C5 C6 110.65(14) . . ?
N2 C5 C4 106.23(14) . . ?
C6 C5 C4 111.60(15) . . ?
N2 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C5 C6 C1 114.58(14) . . ?
C5 C6 H6A 108.6 . . ?
C1 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C1 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
N2 C7 C8 117.70(15) . . ?
N2 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
N4 C8 C9 123.08(17) . . ?
N4 C8 C7 115.74(15) . . ?
C9 C8 C7 121.12(16) . . ?
C8 C9 C10 117.68(17) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C11 C10 C9 119.91(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 118.68(17) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N4 C12 C11 122.56(17) . . ?
N4 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N1 C13 C14 118.15(15) . . ?
N1 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
N3 C14 C15 121.72(17) . . ?
N3 C14 C13 114.28(15) . . ?
C15 C14 C13 123.99(16) . . ?
C14 C15 C16 119.54(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.73(17) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 118.63(17) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
N3 C18 C17 122.95(17) . . ?
N3 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C1 O1 Co1 119.98(10) . . ?
C1 O1 H01 110.2(18) . . ?
Co1 O1 H01 118.8(19) . . ?
N5 O2 Co1 111.24(10) . . ?
C13 N1 C3 120.63(15) . . ?
C13 N1 Co1 115.47(12) . . ?
C3 N1 Co1 123.75(11) . . ?
C7 N2 C5 118.54(15) . . ?
C7 N2 Co1 118.27(12) . . ?
C5 N2 Co1 122.26(11) . . ?
C18 N3 C14 118.17(15) . . ?
C18 N3 Co1 127.60(12) . . ?
C14 N3 Co1 111.91(11) . . ?
C12 N4 C8 118.09(15) . . ?
C12 N4 Co1 129.32(12) . . ?
C8 N4 Co1 112.57(11) . . ?
O4 N5 O3 123.17(17) . . ?
O4 N5 O2 118.15(16) . . ?
O3 N5 O2 118.67(15) . . ?
O7 N6 O5 119.73(17) . . ?
O7 N6 O6 120.41(15) . . ?
O5 N6 O6 119.86(16) . . ?

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
O1 C1 C2 C3 72.69(19) . . . . ?
C6 C1 C2 C3 -51.6(2) . . . . ?
C1 C2 C3 N1 -66.36(19) . . . . ?
C1 C2 C3 C4 55.79(19) . . . . ?
N1 C3 C4 C5 62.35(19) . . . . ?
C2 C3 C4 C5 -56.30(19) . . . . ?
C3 C4 C5 N2 -68.11(19) . . . . ?
C3 C4 C5 C6 52.58(19) . . . . ?
N2 C5 C6 C1 70.13(19) . . . . ?
C4 C5 C6 C1 -47.94(19) . . . . ?
O1 C1 C6 C5 -75.04(18) . . . . ?
C2 C1 C6 C5 47.6(2) . . . . ?
N2 C7 C8 N4 -2.0(2) . . . . ?
N2 C7 C8 C9 -179.23(16) . . . . ?
N4 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C10 177.92(16) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 N4 -0.2(3) . . . . ?
N1 C13 C14 N3 -12.8(2) . . . . ?
N1 C13 C14 C15 168.49(17) . . . . ?
N3 C14 C15 C16 -2.5(3) . . . . ?
C13 C14 C15 C16 176.10(16) . . . . ?
C14 C15 C16 C17 -2.1(3) . . . . ?
C15 C16 C17 C18 3.7(3) . . . . ?
C16 C17 C18 N3 -0.8(3) . . . . ?
C2 C1 O1 Co1 -71.32(16) . . . . ?
C6 C1 O1 Co1 53.41(17) . . . . ?
C14 C13 N1 C3 171.04(15) . . . . ?
C14 C13 N1 Co1 -4.5(2) . . . . ?
C2 C3 N1 C13 -113.03(18) . . . . ?
C4 C3 N1 C13 126.58(17) . . . . ?
C2 C3 N1 Co1 62.16(17) . . . . ?
C4 C3 N1 Co1 -58.24(18) . . . . ?
C8 C7 N2 C5 168.93(15) . . . . ?
C8 C7 N2 Co1 -0.3(2) . . . . ?
C6 C5 N2 C7 144.46(16) . . . . ?
C4 C5 N2 C7 -94.25(19) . . . . ?
C6 C5 N2 Co1 -46.78(18) . . . . ?
C4 C5 N2 Co1 74.51(16) . . . . ?
C17 C18 N3 C14 -3.8(2) . . . . ?
C17 C18 N3 Co1 157.40(13) . . . . ?
C15 C14 N3 C18 5.4(2) . . . . ?
C13 C14 N3 C18 -173.31(15) . . . . ?
C15 C14 N3 Co1 -158.59(13) . . . . ?
C13 C14 N3 Co1 22.65(17) . . . . ?
C11 C12 N4 C8 0.7(3) . . . . ?
C11 C12 N4 Co1 179.20(13) . . . . ?
C9 C8 N4 C12 -1.0(2) . . . . ?
C7 C8 N4 C12 -178.22(15) . . . . ?
C9 C8 N4 Co1 -179.77(14) . . . . ?
C7 C8 N4 Co1 3.01(18) . . . . ?
Co1 O2 N5 O4 -175.72(13) . . . . ?
Co1 O2 N5 O3 4.62(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O6 1.00 2.56 3.155(2) 118.2 .
C3 H3 O7 1.00 2.60 3.162(2) 115.6 2_556
C4 H4B O7 0.99 2.57 3.200(2) 121.5 2_556
C6 H6B O4 0.99 2.40 3.320(2) 154.2 1_655
C7 H7 O5 0.95 2.45 3.208(2) 136.4 4_666
C12 H12 O7 0.95 2.57 3.242(2) 127.6 2_456
C13 H13 O6 0.95 2.50 3.328(2) 145.9 2_556
C18 H18 O2 0.95 2.56 3.088(2) 115.5 .
O1 H01 O5 0.84(3) 1.86(3) 2.668(2) 161(3) .
O1 H01 N6 0.84(3) 2.58(3) 3.3131(19) 147(2) .

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.063

