# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1583578'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2017-12-18 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         'C24 H24 Co N12 O2, 2(C6 N5), 2(H2O)'
_chemical_formula_sum            'C36 H28 Co N22 O4'
_chemical_formula_weight         891.73

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0992(8)
_cell_length_b                   11.4165(10)
_cell_length_c                   11.7630(11)
_cell_angle_alpha                103.655(8)
_cell_angle_beta                 103.501(8)
_cell_angle_gamma                97.011(8)
_cell_volume                     1009.48(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5660
_cell_measurement_theta_min      3.5220
_cell_measurement_theta_max      28.9430

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             457
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4556
_exptl_crystal_size_mid          0.3384
_exptl_crystal_size_min          0.2188
_exptl_absorpt_coefficient_mu    0.496
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3438
_diffrn_reflns_number            10541
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.970
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4180
_reflns_number_gt                3586
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²+0.3145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0178(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4180
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.5000 0.01946(10) Uani 1 2 d S . P . .
O2 O 0.24359(17) 0.80343(11) 0.47599(13) 0.0309(3) Uani 1 1 d . . . . .
O1 O 0.27217(16) 0.56253(12) 0.43496(11) 0.0260(3) Uani 1 1 d . . . . .
N30 N 0.77110(16) 0.67575(11) 0.31188(11) 0.0203(3) Uani 1 1 d . . . . .
N60 N 0.81767(18) 0.63863(13) 0.07070(12) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.29123(17) 0.90034(12) 0.73781(12) 0.0248(3) Uani 1 1 d . . . . .
N10 N 0.60326(17) 0.54970(11) 0.36818(11) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.1615(2) 0.87860(14) 1.00262(15) 0.0443(4) Uani 1 1 d . . . . .
N20 N 0.60635(17) 0.49091(12) 0.25265(11) 0.0220(3) Uani 1 1 d . . . . .
N50 N 0.36320(16) 0.31355(11) 0.41019(11) 0.0205(3) Uani 1 1 d . . . . .
N40 N 0.8824(2) 0.78349(12) 0.31397(15) 0.0270(3) Uani 1 1 d . . . . .
N5 N 0.4106(2) 1.14856(13) 1.00824(14) 0.0382(4) Uani 1 1 d . . . . .
C61 C 0.7438(2) 0.54223(14) 0.10014(14) 0.0221(3) Uani 1 1 d . . . . .
N6 N 0.5293(2) 1.11633(14) 0.65827(14) 0.0379(4) Uani 1 1 d . . . . .
C7 C 0.7004(2) 0.66065(13) 0.40275(14) 0.0199(3) Uani 1 1 d . . . . .
N2 N 0.0428(2) 0.61469(13) 0.64849(15) 0.0382(4) Uani 1 1 d . . . . .
C62 C 0.6971(2) 0.42331(15) 0.02342(15) 0.0290(4) Uani 1 1 d . . . . .
H62 H 0.6447 0.3578 0.0478 0.035 Uiso 1 1 calc R U . . .
C51 C 0.2788(2) 0.25771(14) 0.47607(14) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.2046(2) 0.82917(14) 0.78687(15) 0.0250(4) Uani 1 1 d . . . . .
C54 C 0.2578(2) 0.13156(15) 0.24310(15) 0.0280(4) Uani 1 1 d . . . . .
H54 H 0.2507 0.0900 0.1615 0.034 Uiso 1 1 calc R U . . .
C21 C 0.7087(2) 0.56803(14) 0.21985(14) 0.0202(3) Uani 1 1 d . . . . .
C53 C 0.1751(2) 0.07531(15) 0.31152(15) 0.0303(4) Uani 1 1 d . . . . .
H53 H 0.1114 -0.0062 0.2777 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1832(2) 0.85931(15) 0.90724(17) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.1165(2) 0.70994(15) 0.70974(16) 0.0278(4) Uani 1 1 d . . . . .
C4 C 0.3780(2) 1.01469(14) 0.79065(14) 0.0248(4) Uani 1 1 d . . . . .
C52 C 0.1852(2) 0.13822(14) 0.43011(15) 0.0269(4) Uani 1 1 d . . . . .
H52 H 0.1296 0.1006 0.4787 0.032 Uiso 1 1 calc R U . . .
C55 C 0.3521(2) 0.25051(14) 0.29596(14) 0.0244(4) Uani 1 1 d . . . . .
H55 H 0.4109 0.2886 0.2493 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4618(2) 1.07171(15) 0.71753(15) 0.0279(4) Uani 1 1 d . . . . .
C64 C 0.8040(2) 0.50139(18) -0.12166(16) 0.0364(4) Uani 1 1 d . . . . .
H64 H 0.8267 0.4899 -0.1988 0.044 Uiso 1 1 calc R U . . .
C63 C 0.7293(2) 0.40334(17) -0.08948(16) 0.0356(4) Uani 1 1 d . . . . .
H63 H 0.7004 0.3233 -0.1440 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3951(2) 1.08774(14) 0.91189(16) 0.0263(4) Uani 1 1 d . . . . .
C65 C 0.8451(2) 0.61639(18) -0.04010(16) 0.0355(4) Uani 1 1 d . . . . .
H65 H 0.8954 0.6834 -0.0635 0.043 Uiso 1 1 calc R U . . .
H1N H 0.989(3) 0.7816(18) 0.3596(18) 0.046(6) Uiso 1 1 d . . . . .
H1O1 H 0.180(3) 0.520(2) 0.4285(19) 0.051(7) Uiso 1 1 d . . . . .
H2O1 H 0.265(3) 0.635(2) 0.454(2) 0.057(7) Uiso 1 1 d . . . . .
H2N H 0.887(3) 0.7747(19) 0.236(2) 0.051(6) Uiso 1 1 d . . . . .
H1O2 H 0.316(3) 0.834(2) 0.446(2) 0.058(7) Uiso 1 1 d . . . . .
H2O2 H 0.262(3) 0.835(2) 0.548(2) 0.069(9) 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 N10 2.0810(12) . ?
Co1 N10 2.0811(12) 2_666 ?
Co1 O1 2.1024(12) 2_666 ?
Co1 O1 2.1024(12) . ?
Co1 N50 2.1658(13) . ?
Co1 N50 2.1658(13) 2_666 ?
O2 H1O2 0.83(2) . ?
O2 H2O2 0.80(3) . ?
O1 H1O1 0.82(2) . ?
O1 H2O1 0.82(2) . ?
N30 C7 1.3600(18) . ?
N30 C21 1.3799(19) . ?
N30 N40 1.4250(17) . ?
N60 C65 1.343(2) . ?
N60 C61 1.344(2) . ?
N1 C1 1.325(2) . ?
N1 C4 1.332(2) . ?
N10 C7 1.3239(19) . ?
N10 N20 1.3738(17) . ?
N3 C3 1.150(2) . ?
N20 C21 1.3200(19) . ?
N50 C55 1.3426(19) . ?
N50 C51 1.3595(19) . ?
N40 H1N 0.91(2) . ?
N40 H2N 0.91(2) . ?
N5 C5 1.150(2) . ?
C61 C62 1.392(2) . ?
C61 C21 1.470(2) . ?
N6 C6 1.150(2) . ?
C7 C51 1.467(2) 2_666 ?
N2 C2 1.153(2) . ?
C62 C63 1.385(2) . ?
C62 H62 0.9500 . ?
C51 C52 1.391(2) . ?
C51 C7 1.467(2) 2_666 ?
C1 C3 1.433(2) . ?
C1 C2 1.436(2) . ?
C54 C53 1.378(2) . ?
C54 C55 1.393(2) . ?
C54 H54 0.9500 . ?
C53 C52 1.388(2) . ?
C53 H53 0.9500 . ?
C4 C6 1.433(2) . ?
C4 C5 1.438(2) . ?
C52 H52 0.9500 . ?
C55 H55 0.9500 . ?
C64 C63 1.380(3) . ?
C64 C65 1.380(3) . ?
C64 H64 0.9500 . ?
C63 H63 0.9500 . ?
C65 H65 0.9500 . ?

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
N10 Co1 N10 180.00(6) . 2_666 ?
N10 Co1 O1 89.32(5) . 2_666 ?
N10 Co1 O1 90.68(5) 2_666 2_666 ?
N10 Co1 O1 90.68(5) . . ?
N10 Co1 O1 89.32(5) 2_666 . ?
O1 Co1 O1 180.0 2_666 . ?
N10 Co1 N50 103.27(5) . . ?
N10 Co1 N50 76.73(5) 2_666 . ?
O1 Co1 N50 91.15(5) 2_666 . ?
O1 Co1 N50 88.86(5) . . ?
N10 Co1 N50 76.72(5) . 2_666 ?
N10 Co1 N50 103.27(5) 2_666 2_666 ?
O1 Co1 N50 88.86(5) 2_666 2_666 ?
O1 Co1 N50 91.14(5) . 2_666 ?
N50 Co1 N50 180.0 . 2_666 ?
H1O2 O2 H2O2 112(2) . . ?
Co1 O1 H1O1 117.8(15) . . ?
Co1 O1 H2O1 122.3(16) . . ?
H1O1 O1 H2O1 110(2) . . ?
C7 N30 C21 105.60(12) . . ?
C7 N30 N40 125.60(13) . . ?
C21 N30 N40 128.78(13) . . ?
C65 N60 C61 116.71(15) . . ?
C1 N1 C4 127.13(14) . . ?
C7 N10 N20 109.42(12) . . ?
C7 N10 Co1 115.28(10) . . ?
N20 N10 Co1 135.10(10) . . ?
C21 N20 N10 106.20(12) . . ?
C55 N50 C51 117.99(13) . . ?
C55 N50 Co1 125.92(10) . . ?
C51 N50 Co1 116.07(10) . . ?
N30 N40 H1N 106.4(13) . . ?
N30 N40 H2N 105.8(14) . . ?
H1N N40 H2N 107.9(18) . . ?
N60 C61 C62 123.75(15) . . ?
N60 C61 C21 116.40(14) . . ?
C62 C61 C21 119.83(14) . . ?
N10 C7 N30 108.59(13) . . ?
N10 C7 C51 120.45(13) . 2_666 ?
N30 C7 C51 130.92(14) . 2_666 ?
C63 C62 C61 118.03(16) . . ?
C63 C62 H62 121.0 . . ?
C61 C62 H62 121.0 . . ?
N50 C51 C52 122.45(14) . . ?
N50 C51 C7 111.38(13) . 2_666 ?
C52 C51 C7 126.17(14) . 2_666 ?
N1 C1 C3 127.33(15) . . ?
N1 C1 C2 116.69(15) . . ?
C3 C1 C2 115.93(14) . . ?
C53 C54 C55 118.70(15) . . ?
C53 C54 H54 120.6 . . ?
C55 C54 H54 120.6 . . ?
N20 C21 N30 110.18(13) . . ?
N20 C21 C61 123.91(14) . . ?
N30 C21 C61 125.87(13) . . ?
C54 C53 C52 119.75(15) . . ?
C54 C53 H53 120.1 . . ?
C52 C53 H53 120.1 . . ?
N3 C3 C1 177.05(18) . . ?
N2 C2 C1 178.65(19) . . ?
N1 C4 C6 116.13(14) . . ?
N1 C4 C5 127.39(15) . . ?
C6 C4 C5 116.47(14) . . ?
C53 C52 C51 118.37(15) . . ?
C53 C52 H52 120.8 . . ?
C51 C52 H52 120.8 . . ?
N50 C55 C54 122.72(15) . . ?
N50 C55 H55 118.6 . . ?
C54 C55 H55 118.6 . . ?
N6 C6 C4 179.33(18) . . ?
C63 C64 C65 119.00(16) . . ?
C63 C64 H64 120.5 . . ?
C65 C64 H64 120.5 . . ?
C64 C63 C62 119.05(17) . . ?
C64 C63 H63 120.5 . . ?
C62 C63 H63 120.5 . . ?
N5 C5 C4 178.37(17) . . ?
N60 C65 C64 123.46(16) . . ?
N60 C65 H65 118.3 . . ?
C64 C65 H65 118.3 . . ?

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
C54 H54 N3 0.95 2.58 3.393(2) 143.8 1_544
C54 H54 N5 0.95 2.61 3.315(2) 131.2 1_544
C52 H52 N40 0.95 2.52 3.127(2) 122.2 2_666
C55 H55 N20 0.95 2.62 3.436(2) 143.9 .
C64 H64 O1 0.95 2.60 3.472(2) 152.2 2_665
N40 H1N O2 0.91(2) 2.14(2) 3.045(2) 172.3(18) 1_655
O1 H1O1 N2 0.82(2) 2.08(2) 2.863(2) 160(2) 2_566
O1 H2O1 O2 0.82(2) 1.91(2) 2.7261(18) 173(2) .
N40 H2N N60 0.91(2) 2.09(2) 2.838(2) 139.1(18) .
O2 H1O2 N6 0.83(2) 2.07(2) 2.889(2) 169(2) 2_676
O2 H2O2 N1 0.80(3) 2.13(3) 2.931(2) 173(2) .

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1583581'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2017-12-18 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         'C26 H20 Co N18 O4'
_chemical_formula_sum            'C26 H20 Co N18 O4'
_chemical_formula_weight         707.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.6207(6)
_cell_length_b                   16.5927(11)
_cell_length_c                   10.1837(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.343(6)
_cell_angle_gamma                90
_cell_volume                     1452.50(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3270
_cell_measurement_theta_min      3.4290
_cell_measurement_theta_max      28.9980

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             722
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2941
_exptl_crystal_size_mid          0.1539
_exptl_crystal_size_min          0.1492
_exptl_absorpt_coefficient_mu    0.662
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3438
_diffrn_reflns_number            5088
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.171
_diffrn_reflns_theta_max         26.499
_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             5088
_reflns_number_gt                3510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.1679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5088
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.0000 0.02058(14) Uani 1 2 d S . P . .
N10 N 0.4646(2) 0.54211(12) 0.1884(2) 0.0234(5) Uani 1 1 d . . . . .
O2 O 0.2314(2) 0.31336(11) 0.29402(18) 0.0361(5) Uani 1 1 d . . . . .
N40 N 0.6618(3) 0.58442(14) 0.4984(2) 0.0239(5) Uani 1 1 d . . . . .
N30 N 0.5545(2) 0.57349(11) 0.38704(19) 0.0199(5) Uani 1 1 d . . . . .
O1 O 0.1912(2) 0.18587(11) 0.2599(2) 0.0403(5) Uani 1 1 d . . . . .
N20 N 0.3456(2) 0.57776(12) 0.2487(2) 0.0230(5) Uani 1 1 d . . . . .
N60 N 0.3824(3) 0.65591(14) 0.5818(2) 0.0320(6) Uani 1 1 d . . . . .
N50 N 0.7179(2) 0.47544(12) 0.1082(2) 0.0225(5) Uani 1 1 d . . . . .
N1 N 0.4173(3) 0.38472(13) 0.0515(2) 0.0291(5) Uani 1 1 d . . . . .
C11 C 0.5892(3) 0.53938(14) 0.2723(2) 0.0207(5) Uani 1 1 d . . . . .
C52 C 0.8721(3) 0.49759(15) 0.3110(3) 0.0240(6) Uani 1 1 d . . . . .
H52 H 0.8809 0.5185 0.3981 0.029 Uiso 1 1 calc R U . . .
C53 C 0.9974(3) 0.46055(16) 0.2588(3) 0.0285(6) Uani 1 1 d . . . . .
H53 H 1.0940 0.4559 0.3097 0.034 Uiso 1 1 calc R U . . .
C51 C 0.7335(3) 0.50346(14) 0.2333(2) 0.0205(5) Uani 1 1 d . . . . .
C61 C 0.3103(3) 0.63821(14) 0.4641(2) 0.0213(6) Uani 1 1 d . . . . .
C62 C 0.1557(3) 0.65694(15) 0.4294(3) 0.0248(6) Uani 1 1 d . . . . .
H62 H 0.1079 0.6413 0.3462 0.030 Uiso 1 1 calc R U . . .
N3 N 0.2453(2) 0.25148(14) 0.2294(2) 0.0255(5) Uani 1 1 d . . . . .
C54 C 0.9808(3) 0.43040(16) 0.1326(3) 0.0299(6) Uani 1 1 d . . . . .
H54 H 1.0651 0.4039 0.0957 0.036 Uiso 1 1 calc R U . . .
C63 C 0.0730(3) 0.69880(15) 0.5180(3) 0.0294(6) Uani 1 1 d . . . . .
H63 H -0.0328 0.7128 0.4970 0.035 Uiso 1 1 calc R U . . .
C21 C 0.4016(3) 0.59687(14) 0.3686(2) 0.0205(6) Uani 1 1 d . . . . .
C65 C 0.2993(3) 0.69665(18) 0.6658(3) 0.0386(8) Uani 1 1 d . . . . .
H65 H 0.3483 0.7103 0.7496 0.046 Uiso 1 1 calc R U . . .
C55 C 0.8398(3) 0.43929(16) 0.0606(3) 0.0278(6) Uani 1 1 d . . . . .
H55 H 0.8290 0.4187 -0.0267 0.033 Uiso 1 1 calc R U . . .
N2 N 0.3179(3) 0.25250(13) 0.1162(2) 0.0335(6) Uani 1 1 d . . . . .
C1 C 0.3687(3) 0.32534(16) 0.0875(2) 0.0245(6) Uani 1 1 d . . . . .
C64 C 0.1472(3) 0.71983(17) 0.6378(3) 0.0357(7) Uani 1 1 d . . . . .
H64 H 0.0942 0.7499 0.6999 0.043 Uiso 1 1 calc R U . . .
H2N H 0.702(3) 0.6321(17) 0.488(3) 0.036(8) Uiso 1 1 d . . . . .
H1N H 0.606(4) 0.5905(19) 0.563(3) 0.046(10) 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 N10 2.086(2) 3_665 ?
Co1 N10 2.086(2) . ?
Co1 N1 2.121(2) . ?
Co1 N1 2.121(2) 3_665 ?
Co1 N50 2.144(2) . ?
Co1 N50 2.144(2) 3_665 ?
N10 C11 1.322(3) . ?
N10 N20 1.369(3) . ?
O2 N3 1.230(3) . ?
N40 N30 1.420(3) . ?
N40 H2N 0.87(3) . ?
N40 H1N 0.85(3) . ?
N30 C11 1.352(3) . ?
N30 C21 1.374(3) . ?
O1 N3 1.233(3) . ?
N20 C21 1.317(3) . ?
N60 C65 1.340(3) . ?
N60 C61 1.341(3) . ?
N50 C55 1.333(3) . ?
N50 C51 1.353(3) . ?
N1 C1 1.142(3) . ?
C11 C51 1.461(3) . ?
C52 C53 1.383(4) . ?
C52 C51 1.386(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.377(4) . ?
C53 H53 0.9500 . ?
C61 C62 1.388(3) . ?
C61 C21 1.467(3) . ?
C62 C63 1.380(4) . ?
C62 H62 0.9500 . ?
N3 N2 1.354(3) . ?
C54 C55 1.379(4) . ?
C54 H54 0.9500 . ?
C63 C64 1.378(4) . ?
C63 H63 0.9500 . ?
C65 C64 1.376(4) . ?
C65 H65 0.9500 . ?
C55 H55 0.9500 . ?
N2 C1 1.325(3) . ?
C64 H64 0.9500 . ?

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
N10 Co1 N10 180.0 3_665 . ?
N10 Co1 N1 90.05(8) 3_665 . ?
N10 Co1 N1 89.95(8) . . ?
N10 Co1 N1 89.95(8) 3_665 3_665 ?
N10 Co1 N1 90.05(8) . 3_665 ?
N1 Co1 N1 180.0 . 3_665 ?
N10 Co1 N50 103.03(8) 3_665 . ?
N10 Co1 N50 76.97(8) . . ?
N1 Co1 N50 89.96(8) . . ?
N1 Co1 N50 90.04(8) 3_665 . ?
N10 Co1 N50 76.97(8) 3_665 3_665 ?
N10 Co1 N50 103.03(8) . 3_665 ?
N1 Co1 N50 90.04(8) . 3_665 ?
N1 Co1 N50 89.96(8) 3_665 3_665 ?
N50 Co1 N50 180.0 . 3_665 ?
C11 N10 N20 108.93(19) . . ?
C11 N10 Co1 114.50(16) . . ?
N20 N10 Co1 136.41(15) . . ?
N30 N40 H2N 105.0(19) . . ?
N30 N40 H1N 105(2) . . ?
H2N N40 H1N 104(3) . . ?
C11 N30 C21 105.8(2) . . ?
C11 N30 N40 124.8(2) . . ?
C21 N30 N40 129.3(2) . . ?
C21 N20 N10 106.6(2) . . ?
C65 N60 C61 116.6(2) . . ?
C55 N50 C51 118.2(2) . . ?
C55 N50 Co1 125.65(17) . . ?
C51 N50 Co1 116.05(16) . . ?
C1 N1 Co1 174.8(2) . . ?
N10 C11 N30 108.8(2) . . ?
N10 C11 C51 120.3(2) . . ?
N30 C11 C51 130.9(2) . . ?
C53 C52 C51 118.5(2) . . ?
C53 C52 H52 120.8 . . ?
C51 C52 H52 120.8 . . ?
C54 C53 C52 119.4(2) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
N50 C51 C52 122.2(2) . . ?
N50 C51 C11 111.7(2) . . ?
C52 C51 C11 126.0(2) . . ?
N60 C61 C62 123.4(2) . . ?
N60 C61 C21 117.4(2) . . ?
C62 C61 C21 119.2(2) . . ?
C63 C62 C61 118.7(2) . . ?
C63 C62 H62 120.7 . . ?
C61 C62 H62 120.7 . . ?
O2 N3 O1 123.2(2) . . ?
O2 N3 N2 121.0(2) . . ?
O1 N3 N2 115.7(2) . . ?
C53 C54 C55 118.8(2) . . ?
C53 C54 H54 120.6 . . ?
C55 C54 H54 120.6 . . ?
C64 C63 C62 118.6(3) . . ?
C64 C63 H63 120.7 . . ?
C62 C63 H63 120.7 . . ?
N20 C21 N30 109.8(2) . . ?
N20 C21 C61 123.4(2) . . ?
N30 C21 C61 126.8(2) . . ?
N60 C65 C64 123.8(3) . . ?
N60 C65 H65 118.1 . . ?
C64 C65 H65 118.1 . . ?
N50 C55 C54 122.9(2) . . ?
N50 C55 H55 118.6 . . ?
C54 C55 H55 118.6 . . ?
C1 N2 N3 112.4(2) . . ?
N1 C1 N2 173.1(3) . . ?
C65 C64 C63 119.0(3) . . ?
C65 C64 H64 120.5 . . ?
C63 C64 H64 120.5 . . ?

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
C52 H52 N40 0.95 2.47 3.087(4) 122.6 .
C55 H55 N20 0.95 2.62 3.434(3) 143.9 3_665
N40 H2N N2 0.87(3) 2.26(3) 3.033(3) 147(2) 2_655
N40 H1N N60 0.85(3) 2.23(3) 2.871(3) 132(3) .
N40 H2N O2 0.87(3) 2.43(3) 2.811(3) 107(2) 3_666

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1583580'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2017-12-18 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         'C26 H28 Co N12 O2, 2(C8 N5)'
_chemical_formula_sum            'C42 H28 Co N22 O2'
_chemical_formula_weight         931.79

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1594(2)
_cell_length_b                   12.3043(4)
_cell_length_c                   12.9843(4)
_cell_angle_alpha                71.278(3)
_cell_angle_beta                 75.397(2)
_cell_angle_gamma                83.503(2)
_cell_volume                     1047.64(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9363
_cell_measurement_theta_min      3.4110
_cell_measurement_theta_max      29.5100

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             477
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6054
_exptl_crystal_size_mid          0.3371
_exptl_crystal_size_min          0.1044
_exptl_absorpt_coefficient_mu    0.478
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3438
_diffrn_reflns_number            17611
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.042
_diffrn_reflns_theta_max         26.499
_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             4330
_reflns_number_gt                3869
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.5733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4330
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.0000 0.01781(9) Uani 1 2 d S . P . .
N10 N 0.55676(18) 0.62659(10) 0.05876(10) 0.0201(3) Uani 1 1 d . . . . .
O1 O 0.78238(17) 0.43042(11) 0.00263(10) 0.0272(3) Uani 1 1 d . . . . .
N40 N 0.5957(2) 0.69066(13) 0.29984(11) 0.0268(3) Uani 1 1 d . . . . .
N50 N 0.42858(18) 0.42270(11) 0.17831(10) 0.0199(3) Uani 1 1 d . . . . .
N60 N 0.6565(2) 0.92450(12) 0.16513(12) 0.0308(3) Uani 1 1 d . . . . .
C11 C 0.5342(2) 0.59954(12) 0.16833(12) 0.0193(3) Uani 1 1 d . . . . .
N30 N 0.58905(18) 0.68883(10) 0.19190(10) 0.0195(3) Uani 1 1 d . . . . .
C55 C 0.3614(2) 0.31707(13) 0.23215(13) 0.0235(3) Uani 1 1 d . . . . .
H55 H 0.3397 0.2716 0.1897 0.028 Uiso 1 1 calc R U . . .
N20 N 0.62243(19) 0.73550(10) 0.00957(11) 0.0214(3) Uani 1 1 d . . . . .
N8 N 0.8551(2) 0.28738(13) 0.21041(13) 0.0367(4) Uani 1 1 d . . . . .
C61 C 0.6920(2) 0.89033(13) 0.07378(13) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.7762(3) -0.00913(15) 0.68442(13) 0.0425(4) Uani 1 1 d . . . . .
C52 C 0.4186(2) 0.44874(14) 0.35566(13) 0.0249(3) Uani 1 1 d . . . . .
H52 H 0.4373 0.4964 0.3969 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7963(2) 0.14646(15) 0.40992(14) 0.0294(4) Uani 1 1 d . . . . .
N5 N 0.8591(3) 0.46814(14) 0.36797(15) 0.0448(4) Uani 1 1 d . . . . .
C54 C 0.3226(2) 0.27182(14) 0.34766(14) 0.0269(4) Uani 1 1 d . . . . .
H54 H 0.2774 0.1961 0.3835 0.032 Uiso 1 1 calc R U . . .
C1 C 0.8136(2) 0.17050(15) 0.50514(14) 0.0306(4) Uani 1 1 d . . . . .
N4 N 0.9102(3) 0.28492(15) 0.70161(14) 0.0503(5) Uani 1 1 d . . . . .
N7 N 0.7145(3) -0.05730(15) 0.42338(14) 0.0492(5) Uani 1 1 d . . . . .
C21 C 0.6412(2) 0.77250(13) 0.09107(12) 0.0195(3) Uani 1 1 d . . . . .
C62 C 0.7608(2) 0.96163(14) -0.03396(14) 0.0281(4) Uani 1 1 d . . . . .
H62 H 0.7839 0.9337 -0.0965 0.034 Uiso 1 1 calc R U . . .
C64 C 0.7576(3) 1.11127(15) 0.04564(17) 0.0360(4) Uani 1 1 d . . . . .
H64 H 0.7789 1.1884 0.0385 0.043 Uiso 1 1 calc R U . . .
C63 C 0.7946(3) 1.07455(15) -0.04752(16) 0.0338(4) Uani 1 1 d . . . . .
H63 H 0.8424 1.1258 -0.1198 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8293(2) 0.22703(14) 0.30047(14) 0.0285(4) Uani 1 1 d . . . . .
C53 C 0.3505(2) 0.33856(15) 0.40959(13) 0.0288(4) Uani 1 1 d . . . . .
H53 H 0.3234 0.3093 0.4888 0.035 Uiso 1 1 calc R U . . .
C51 C 0.4585(2) 0.48699(13) 0.23983(12) 0.0191(3) Uani 1 1 d . . . . .
C5 C 0.8570(3) 0.37929(16) 0.43166(15) 0.0317(4) Uani 1 1 d . . . . .
C1O1 C 0.9331(3) 0.41897(17) -0.08951(15) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.8503(3) 0.27262(15) 0.51744(15) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.7919(3) 0.07101(15) 0.60740(15) 0.0328(4) Uani 1 1 d . . . . .
C65 C 0.6895(3) 1.03456(15) 0.14902(17) 0.0377(4) Uani 1 1 d . . . . .
H65 H 0.6643 1.0610 0.2125 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7501(3) 0.03346(16) 0.41842(14) 0.0350(4) Uani 1 1 d . . . . .
C4 C 0.8822(3) 0.27645(16) 0.62143(17) 0.0382(4) Uani 1 1 d . . . . .
H1N H 0.602(3) 0.761(2) 0.2937(18) 0.044(6) Uiso 1 1 d . . . . .
H1O H 0.806(3) 0.3951(18) 0.0597(18) 0.037(6) Uiso 1 1 d . . . . .
H2N H 0.708(3) 0.6543(18) 0.3127(17) 0.039(6) Uiso 1 1 d . . . . .
H1C H 0.896(3) 0.375(2) -0.133(2) 0.057(7) Uiso 1 1 d . . . . .
H2C H 0.961(4) 0.495(2) -0.144(2) 0.072(8) Uiso 1 1 d . . . . .
H3C H 1.053(4) 0.390(2) -0.067(2) 0.064(7) 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 N10 2.0581(12) . ?
Co1 N10 2.0582(12) 2_665 ?
Co1 O1 2.1085(12) 2_665 ?
Co1 O1 2.1085(12) . ?
Co1 N50 2.1507(12) 2_665 ?
Co1 N50 2.1508(12) . ?
N10 C11 1.3241(19) . ?
N10 N20 1.3662(17) . ?
O1 C1O1 1.428(2) . ?
O1 H1O 0.78(2) . ?
N40 N30 1.4217(17) . ?
N40 H1N 0.85(2) . ?
N40 H2N 0.90(2) . ?
N50 C55 1.3407(19) . ?
N50 C51 1.3566(19) . ?
N60 C61 1.339(2) . ?
N60 C65 1.341(2) . ?
C11 N30 1.3523(19) . ?
C11 C51 1.471(2) . ?
N30 C21 1.3742(19) . ?
C55 C54 1.388(2) . ?
C55 H55 0.9500 . ?
N20 C21 1.3190(19) . ?
N8 C8 1.148(2) . ?
C61 C62 1.390(2) . ?
C61 C21 1.468(2) . ?
N2 C2 1.149(2) . ?
C52 C51 1.387(2) . ?
C52 C53 1.391(2) . ?
C52 H52 0.9500 . ?
C6 C1 1.397(2) . ?
C6 C8 1.427(2) . ?
C6 C7 1.429(3) . ?
N5 C5 1.138(2) . ?
C54 C53 1.380(2) . ?
C54 H54 0.9500 . ?
C1 C3 1.378(3) . ?
C1 C2 1.477(2) . ?
N4 C4 1.147(3) . ?
N7 C7 1.152(3) . ?
C62 C63 1.385(2) . ?
C62 H62 0.9500 . ?
C64 C65 1.375(3) . ?
C64 C63 1.378(3) . ?
C64 H64 0.9500 . ?
C63 H63 0.9500 . ?
C53 H53 0.9500 . ?
C5 C3 1.419(2) . ?
C1O1 H1C 0.99(3) . ?
C1O1 H2C 0.98(3) . ?
C1O1 H3C 0.97(3) . ?
C3 C4 1.441(3) . ?
C65 H65 0.9500 . ?

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
N10 Co1 N10 180.0 . 2_665 ?
N10 Co1 O1 90.41(5) . 2_665 ?
N10 Co1 O1 89.59(5) 2_665 2_665 ?
N10 Co1 O1 89.59(5) . . ?
N10 Co1 O1 90.41(5) 2_665 . ?
O1 Co1 O1 180.0 2_665 . ?
N10 Co1 N50 103.15(5) . 2_665 ?
N10 Co1 N50 76.86(5) 2_665 2_665 ?
O1 Co1 N50 87.21(5) 2_665 2_665 ?
O1 Co1 N50 92.79(5) . 2_665 ?
N10 Co1 N50 76.86(5) . . ?
N10 Co1 N50 103.14(5) 2_665 . ?
O1 Co1 N50 92.79(5) 2_665 . ?
O1 Co1 N50 87.21(5) . . ?
N50 Co1 N50 180.0 2_665 . ?
C11 N10 N20 109.30(12) . . ?
C11 N10 Co1 116.18(10) . . ?
N20 N10 Co1 134.46(10) . . ?
C1O1 O1 Co1 127.94(11) . . ?
C1O1 O1 H1O 112.0(16) . . ?
Co1 O1 H1O 118.8(15) . . ?
N30 N40 H1N 105.3(15) . . ?
N30 N40 H2N 105.7(13) . . ?
H1N N40 H2N 109(2) . . ?
C55 N50 C51 118.29(13) . . ?
C55 N50 Co1 125.58(10) . . ?
C51 N50 Co1 116.12(10) . . ?
C61 N60 C65 116.64(15) . . ?
N10 C11 N30 108.53(13) . . ?
N10 C11 C51 119.23(13) . . ?
N30 C11 C51 132.25(13) . . ?
C11 N30 C21 105.85(12) . . ?
C11 N30 N40 125.56(13) . . ?
C21 N30 N40 128.55(13) . . ?
N50 C55 C54 122.37(15) . . ?
N50 C55 H55 118.8 . . ?
C54 C55 H55 118.8 . . ?
C21 N20 N10 106.36(12) . . ?
N60 C61 C62 123.81(15) . . ?
N60 C61 C21 116.33(14) . . ?
C62 C61 C21 119.73(14) . . ?
C51 C52 C53 117.97(15) . . ?
C51 C52 H52 121.0 . . ?
C53 C52 H52 121.0 . . ?
C1 C6 C8 124.34(16) . . ?
C1 C6 C7 119.64(15) . . ?
C8 C6 C7 115.97(15) . . ?
C53 C54 C55 118.91(15) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
C3 C1 C6 129.67(17) . . ?
C3 C1 C2 115.35(16) . . ?
C6 C1 C2 114.98(16) . . ?
N20 C21 N30 109.94(13) . . ?
N20 C21 C61 123.24(13) . . ?
N30 C21 C61 126.56(14) . . ?
C63 C62 C61 118.05(16) . . ?
C63 C62 H62 121.0 . . ?
C61 C62 H62 121.0 . . ?
C65 C64 C63 119.02(16) . . ?
C65 C64 H64 120.5 . . ?
C63 C64 H64 120.5 . . ?
C64 C63 C62 118.85(17) . . ?
C64 C63 H63 120.6 . . ?
C62 C63 H63 120.6 . . ?
N8 C8 C6 176.53(19) . . ?
C54 C53 C52 119.77(15) . . ?
C54 C53 H53 120.1 . . ?
C52 C53 H53 120.1 . . ?
N50 C51 C52 122.67(14) . . ?
N50 C51 C11 111.47(13) . . ?
C52 C51 C11 125.85(14) . . ?
N5 C5 C3 175.7(2) . . ?
O1 C1O1 H1C 113.4(14) . . ?
O1 C1O1 H2C 109.3(15) . . ?
H1C C1O1 H2C 104(2) . . ?
O1 C1O1 H3C 111.7(15) . . ?
H1C C1O1 H3C 112(2) . . ?
H2C C1O1 H3C 106(2) . . ?
C1 C3 C5 123.39(17) . . ?
C1 C3 C4 120.72(16) . . ?
C5 C3 C4 115.89(17) . . ?
N2 C2 C1 177.4(2) . . ?
N60 C65 C64 123.63(17) . . ?
N60 C65 H65 118.2 . . ?
C64 C65 H65 118.2 . . ?
N7 C7 C6 178.8(2) . . ?
N4 C4 C3 176.7(2) . . ?

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
C55 H55 N20 0.95 2.56 3.374(2) 143.7 2_665
C52 H52 N40 0.95 2.56 3.162(2) 121.6 .
C54 H54 N7 0.95 2.55 3.256(2) 131.1 2_656
N40 H1N N60 0.85(2) 2.16(2) 2.863(2) 140(2) .
O1 H1O N8 0.78(2) 2.07(2) 2.8461(19) 174(2) .
N40 H2N N5 0.90(2) 2.39(2) 3.155(2) 143.0(17) .


_refine_diff_density_max         0.610
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1583582'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2017-12-18 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         'C26 H20 Co N14 Se2'
_chemical_formula_sum            'C26 H20 Co N14 Se2'
_chemical_formula_weight         745.41

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5646(4)
_cell_length_b                   10.1344(3)
_cell_length_c                   19.0783(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.986(5)
_cell_angle_gamma                90
_cell_volume                     1434.29(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6097
_cell_measurement_theta_min      3.1720
_cell_measurement_theta_max      28.2540

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             738
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4236
_exptl_crystal_size_mid          0.2460
_exptl_crystal_size_min          0.1476
_exptl_absorpt_coefficient_mu    3.181
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_T_max  0.657
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3438
_diffrn_reflns_number            11569
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2930
_reflns_number_gt                2609
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+2.5159P] 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         2930
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Se1 Se 0.48708(5) 0.22924(4) 0.24825(2) 0.04171(13) Uani 1 1 d . . . . .
Co1 Co 0.0000 0.0000 0.0000 0.02237(14) Uani 1 2 d S . P . .
N50 N -0.1907(3) 0.0983(2) 0.02544(15) 0.0270(5) Uani 1 1 d . . . . .
N20 N -0.0607(3) -0.2571(2) 0.08113(15) 0.0257(5) Uani 1 1 d . . . . .
N10 N 0.0221(3) -0.1889(3) 0.04742(16) 0.0303(6) Uani 1 1 d . . . . .
N40 N 0.2649(4) -0.4915(3) 0.09089(19) 0.0361(6) Uani 1 1 d . . . . .
N30 N 0.1428(3) -0.3845(2) 0.07766(15) 0.0288(5) Uani 1 1 d . . . . .
N60 N 0.0372(4) -0.5966(3) 0.14646(16) 0.0335(6) Uani 1 1 d . . . . .
N1 N 0.2173(3) 0.0707(3) 0.11051(15) 0.0300(6) Uani 1 1 d . . . . .
C53 C -0.4545(5) 0.2319(4) 0.0411(2) 0.0376(8) Uani 1 1 d . . . . .
H53 H -0.5460 0.2768 0.0460 0.045 Uiso 1 1 calc R U . . .
C52 C -0.3810(4) 0.2880(3) -0.0019(2) 0.0341(7) Uani 1 1 d . . . . .
H52 H -0.4216 0.3715 -0.0273 0.041 Uiso 1 1 calc R U . . .
C55 C -0.2626(4) 0.0455(3) 0.0672(2) 0.0316(7) Uani 1 1 d . . . . .
H55 H -0.2227 -0.0390 0.0911 0.038 Uiso 1 1 calc R U . . .
C51 C -0.2469(4) 0.2199(3) -0.00716(18) 0.0279(6) Uani 1 1 d . . . . .
C64 C -0.1148(4) -0.6668(3) 0.21755(19) 0.0352(7) Uani 1 1 d . . . . .
H64 H -0.1365 -0.7348 0.2459 0.042 Uiso 1 1 calc R U . . .
C62 C -0.1541(4) -0.4458(3) 0.16707(19) 0.0327(7) Uani 1 1 d . . . . .
H62 H -0.2051 -0.3600 0.1591 0.039 Uiso 1 1 calc R U . . .
C63 C -0.1955(5) -0.5448(3) 0.2072(2) 0.0362(7) Uani 1 1 d . . . . .
H63 H -0.2765 -0.5280 0.2266 0.043 Uiso 1 1 calc R U . . .
C61 C -0.0363(4) -0.4781(3) 0.13968(18) 0.0286(6) Uani 1 1 d . . . . .
C54 C -0.3938(5) 0.1103(3) 0.0768(2) 0.0363(7) Uani 1 1 d . . . . .
H54 H -0.4410 0.0712 0.1076 0.044 Uiso 1 1 calc R U . . .
C1 C 0.3244(4) 0.1314(3) 0.16439(18) 0.0264(6) Uani 1 1 d . . . . .
C21 C 0.0128(4) -0.3746(3) 0.09945(17) 0.0271(6) Uani 1 1 d . . . . .
C11 C 0.1444(4) -0.2659(3) 0.04481(18) 0.0280(6) Uani 1 1 d . . . . .
C65 C -0.0018(5) -0.6890(3) 0.1862(2) 0.0374(8) Uani 1 1 d . . . . .
H65 H 0.0509 -0.7740 0.1930 0.045 Uiso 1 1 calc R U . . .
H1N H 0.369(6) -0.473(4) 0.140(3) 0.047(11) Uiso 1 1 d . . . . .
H2N H 0.215(6) -0.565(5) 0.102(3) 0.055(12) 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
Se1 C1 1.805(3) . ?
Co1 N10 2.086(3) 3 ?
Co1 N10 2.086(3) . ?
Co1 N1 2.121(3) . ?
Co1 N1 2.121(3) 3 ?
Co1 N50 2.165(2) 3 ?
Co1 N50 2.165(2) . ?
N50 C55 1.338(4) . ?
N50 C51 1.356(4) . ?
N20 C21 1.311(4) . ?
N20 N10 1.360(3) . ?
N10 C11 1.327(4) . ?
N40 N30 1.439(4) . ?
N40 H1N 0.93(4) . ?
N40 H2N 0.94(5) . ?
N30 C11 1.358(4) . ?
N30 C21 1.372(4) . ?
N60 C61 1.332(4) . ?
N60 C65 1.348(4) . ?
N1 C1 1.155(4) . ?
C53 C54 1.379(5) . ?
C53 C52 1.381(5) . ?
C53 H53 0.9500 . ?
C52 C51 1.386(4) . ?
C52 H52 0.9500 . ?
C55 C54 1.390(4) . ?
C55 H55 0.9500 . ?
C51 C11 1.460(4) 3 ?
C64 C63 1.382(5) . ?
C64 C65 1.387(5) . ?
C64 H64 0.9500 . ?
C62 C61 1.388(4) . ?
C62 C63 1.411(5) . ?
C62 H62 0.9500 . ?
C63 H63 0.9500 . ?
C61 C21 1.480(4) . ?
C54 H54 0.9500 . ?
C11 C51 1.460(4) 3 ?
C65 H65 0.9500 . ?

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
N10 Co1 N10 180.0 3 . ?
N10 Co1 N1 88.02(10) 3 . ?
N10 Co1 N1 91.98(10) . . ?
N10 Co1 N1 91.98(10) 3 3 ?
N10 Co1 N1 88.02(10) . 3 ?
N1 Co1 N1 180.0 . 3 ?
N10 Co1 N50 103.91(10) 3 3 ?
N10 Co1 N50 76.09(10) . 3 ?
N1 Co1 N50 89.58(9) . 3 ?
N1 Co1 N50 90.41(9) 3 3 ?
N10 Co1 N50 76.09(10) 3 . ?
N10 Co1 N50 103.91(10) . . ?
N1 Co1 N50 90.42(9) . . ?
N1 Co1 N50 89.59(9) 3 . ?
N50 Co1 N50 180.0 3 . ?
C55 N50 C51 118.2(3) . . ?
C55 N50 Co1 124.9(2) . . ?
C51 N50 Co1 116.73(19) . . ?
C21 N20 N10 107.0(2) . . ?
C11 N10 N20 109.1(2) . . ?
C11 N10 Co1 115.2(2) . . ?
N20 N10 Co1 135.7(2) . . ?
N30 N40 H1N 106(2) . . ?
N30 N40 H2N 105(3) . . ?
H1N N40 H2N 104(4) . . ?
C11 N30 C21 105.8(2) . . ?
C11 N30 N40 125.0(3) . . ?
C21 N30 N40 129.1(3) . . ?
C61 N60 C65 116.3(3) . . ?
C1 N1 Co1 167.6(3) . . ?
C54 C53 C52 119.4(3) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
C53 C52 C51 118.6(3) . . ?
C53 C52 H52 120.7 . . ?
C51 C52 H52 120.7 . . ?
N50 C55 C54 122.2(3) . . ?
N50 C55 H55 118.9 . . ?
C54 C55 H55 118.9 . . ?
N50 C51 C52 122.4(3) . . ?
N50 C51 C11 110.7(3) . 3 ?
C52 C51 C11 126.9(3) . 3 ?
C63 C64 C65 119.4(3) . . ?
C63 C64 H64 120.3 . . ?
C65 C64 H64 120.3 . . ?
C61 C62 C63 117.6(3) . . ?
C61 C62 H62 121.2 . . ?
C63 C62 H62 121.2 . . ?
C64 C63 C62 118.1(3) . . ?
C64 C63 H63 121.0 . . ?
C62 C63 H63 121.0 . . ?
N60 C61 C62 125.0(3) . . ?
N60 C61 C21 116.5(3) . . ?
C62 C61 C21 118.4(3) . . ?
C53 C54 C55 119.1(3) . . ?
C53 C54 H54 120.4 . . ?
C55 C54 H54 120.4 . . ?
N1 C1 Se1 178.5(3) . . ?
N20 C21 N30 109.9(3) . . ?
N20 C21 C61 124.0(3) . . ?
N30 C21 C61 126.1(3) . . ?
N10 C11 N30 108.2(3) . . ?
N10 C11 C51 120.7(3) . 3 ?
N30 C11 C51 131.1(3) . 3 ?
N60 C65 C64 123.5(3) . . ?
N60 C65 H65 118.2 . . ?
C64 C65 H65 118.2 . . ?

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
C52 H52 N40 0.95 2.53 3.132(5) 121.8 3
N40 H1N Se1 0.93(4) 2.77(4) 3.524(3) 139(3) 2_645
N40 H2N N60 0.94(5) 2.10(4) 2.851(4) 136(4) .

_refine_diff_density_max         0.962
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1583579'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2017-12-18 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         'C24 H24 Co N12 O2, 2(C3 N3 O2)'
_chemical_formula_sum            'C30 H24 Co N18 O6'
_chemical_formula_weight         791.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.6946(3)
_cell_length_b                   13.5526(6)
_cell_length_c                   16.7231(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.741(4)
_cell_angle_gamma                90
_cell_volume                     1707.43(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3703
_cell_measurement_theta_min      4.0030
_cell_measurement_theta_max      29.2800

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             810
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5603
_exptl_crystal_size_mid          0.1479
_exptl_crystal_size_min          0.1042
_exptl_absorpt_coefficient_mu    0.576
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3438
_diffrn_reflns_number            10955
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         26.499
_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             3536
_reflns_number_gt                2931
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+1.0184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3536
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.0000 0.02088(12) Uani 1 2 d S . P . .
O3 O 0.73673(19) 0.72776(11) 0.12064(10) 0.0332(4) Uani 1 1 d . . . . .
O1 O 0.6624(2) 0.53148(13) 0.11536(10) 0.0281(3) Uani 1 1 d . . . . .
N50 N 0.3480(2) 0.63095(12) 0.00839(10) 0.0223(4) Uani 1 1 d . . . . .
O2 O 0.5582(2) 0.73713(14) 0.20706(12) 0.0535(5) Uani 1 1 d . . . . .
N4 N 0.6488(2) 0.77665(13) 0.16278(10) 0.0260(4) Uani 1 1 d . . . . .
N60 N 0.0746(2) 0.16424(14) 0.17759(12) 0.0346(4) Uani 1 1 d . . . . .
N10 N 0.3652(2) 0.39174(12) 0.05490(10) 0.0225(4) Uani 1 1 d . . . . .
N20 N 0.2215(2) 0.38827(12) 0.09250(10) 0.0244(4) Uani 1 1 d . . . . .
N30 N 0.3446(2) 0.24099(12) 0.09675(10) 0.0226(4) Uani 1 1 d . . . . .
N40 N 0.3912(3) 0.14081(14) 0.11474(15) 0.0363(5) Uani 1 1 d . . . . .
N3 N 0.8143(4) 0.95425(17) 0.05321(16) 0.0601(7) Uani 1 1 d . . . . .
N2 N 0.4817(3) 0.97672(16) 0.24537(13) 0.0496(6) Uani 1 1 d . . . . .
C65 C -0.0509(3) 0.1314(2) 0.21656(15) 0.0411(6) Uani 1 1 d . . . . .
H65 H -0.0526 0.0630 0.2289 0.049 Uiso 1 1 calc R U . . .
C53 C 0.1809(3) 0.81069(16) 0.02120(13) 0.0300(5) Uani 1 1 d . . . . .
H53 H 0.1241 0.8720 0.0261 0.036 Uiso 1 1 calc R U . . .
C61 C 0.0744(3) 0.26100(16) 0.16104(12) 0.0250(4) Uani 1 1 d . . . . .
C54 C 0.1190(3) 0.72550(16) 0.05064(13) 0.0286(5) Uani 1 1 d . . . . .
H54 H 0.0185 0.7272 0.0755 0.034 Uiso 1 1 calc R U . . .
C1 C 0.6520(3) 0.87697(16) 0.15711(13) 0.0293(5) Uani 1 1 d . . . . .
C51 C 0.4064(2) 0.71522(14) -0.02124(11) 0.0218(4) Uani 1 1 d . . . . .
C62 C -0.0474(3) 0.32689(18) 0.18194(14) 0.0338(5) Uani 1 1 d . . . . .
H62 H -0.0438 0.3950 0.1689 0.041 Uiso 1 1 calc R U . . .
C21 C 0.2111(2) 0.29669(15) 0.11737(12) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.4375(2) 0.30310(14) 0.05810(11) 0.0209(4) Uani 1 1 d . . . . .
C52 C 0.3276(3) 0.80622(15) -0.01588(13) 0.0267(4) Uani 1 1 d . . . . .
H52 H 0.3723 0.8640 -0.0368 0.032 Uiso 1 1 calc R U . . .
C55 C 0.2059(3) 0.63676(16) 0.04343(12) 0.0266(4) Uani 1 1 d . . . . .
H55 H 0.1631 0.5782 0.0640 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5577(3) 0.93210(17) 0.20555(13) 0.0339(5) Uani 1 1 d . . . . .
C3 C 0.7426(3) 0.92042(17) 0.10016(15) 0.0376(5) Uani 1 1 d . . . . .
C64 C -0.1763(3) 0.1910(2) 0.23949(14) 0.0404(6) Uani 1 1 d . . . . .
H64 H -0.2628 0.1642 0.2666 0.049 Uiso 1 1 calc R U . . .
C63 C -0.1745(3) 0.2903(2) 0.22252(15) 0.0417(6) Uani 1 1 d . . . . .
H63 H -0.2590 0.3334 0.2383 0.050 Uiso 1 1 calc R U . . .
H2O H 0.685(3) 0.592(2) 0.1242(16) 0.045(8) Uiso 1 1 d . . . . .
H1O H 0.624(4) 0.520(2) 0.156(2) 0.063(10) Uiso 1 1 d . . . . .
H2N H 0.301(4) 0.107(2) 0.0791(18) 0.057(9) Uiso 1 1 d . . . . .
H1N H 0.379(4) 0.134(2) 0.167(2) 0.080(11) 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 N10 2.1116(15) 3_665 ?
Co1 N10 2.1116(15) . ?
Co1 O1 2.1175(15) . ?
Co1 O1 2.1176(15) 3_665 ?
Co1 N50 2.1458(16) . ?
Co1 N50 2.1459(16) 3_665 ?
O3 N4 1.260(2) . ?
O1 H2O 0.84(3) . ?
O1 H1O 0.80(3) . ?
N50 C55 1.344(2) . ?
N50 C51 1.357(3) . ?
O2 N4 1.237(2) . ?
N4 C1 1.363(3) . ?
N60 C61 1.340(3) . ?
N60 C65 1.345(3) . ?
N10 C11 1.320(2) . ?
N10 N20 1.379(2) . ?
N20 C21 1.317(3) . ?
N30 C11 1.351(2) . ?
N30 C21 1.374(3) . ?
N30 N40 1.421(2) . ?
N40 H2N 0.94(3) . ?
N40 H1N 0.91(4) . ?
N3 C3 1.143(3) . ?
N2 C2 1.145(3) . ?
C65 C64 1.372(4) . ?
C65 H65 0.9500 . ?
C53 C54 1.377(3) . ?
C53 C52 1.396(3) . ?
C53 H53 0.9500 . ?
C61 C62 1.390(3) . ?
C61 C21 1.478(3) . ?
C54 C55 1.393(3) . ?
C54 H54 0.9500 . ?
C1 C2 1.407(3) . ?
C1 C3 1.418(3) . ?
C51 C52 1.385(3) . ?
C51 C11 1.479(3) 3_665 ?
C62 C63 1.390(3) . ?
C62 H62 0.9500 . ?
C11 C51 1.479(3) 3_665 ?
C52 H52 0.9500 . ?
C55 H55 0.9500 . ?
C64 C63 1.377(4) . ?
C64 H64 0.9500 . ?
C63 H63 0.9500 . ?

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
N10 Co1 N10 180.0 3_665 . ?
N10 Co1 O1 90.30(7) 3_665 . ?
N10 Co1 O1 89.70(7) . . ?
N10 Co1 O1 89.70(7) 3_665 3_665 ?
N10 Co1 O1 90.30(7) . 3_665 ?
O1 Co1 O1 180.0 . 3_665 ?
N10 Co1 N50 77.07(6) 3_665 . ?
N10 Co1 N50 102.93(6) . . ?
O1 Co1 N50 90.13(6) . . ?
O1 Co1 N50 89.87(6) 3_665 . ?
N10 Co1 N50 102.93(6) 3_665 3_665 ?
N10 Co1 N50 77.07(6) . 3_665 ?
O1 Co1 N50 89.87(6) . 3_665 ?
O1 Co1 N50 90.13(6) 3_665 3_665 ?
N50 Co1 N50 180.0 . 3_665 ?
Co1 O1 H2O 114.8(18) . . ?
Co1 O1 H1O 118(2) . . ?
H2O O1 H1O 98(3) . . ?
C55 N50 C51 117.97(17) . . ?
C55 N50 Co1 125.44(14) . . ?
C51 N50 Co1 116.53(12) . . ?
O2 N4 O3 122.61(18) . . ?
O2 N4 C1 119.60(18) . . ?
O3 N4 C1 117.77(17) . . ?
C61 N60 C65 117.0(2) . . ?
C11 N10 N20 108.70(15) . . ?
C11 N10 Co1 114.19(12) . . ?
N20 N10 Co1 137.05(13) . . ?
C21 N20 N10 106.39(16) . . ?
C11 N30 C21 105.85(16) . . ?
C11 N30 N40 124.16(16) . . ?
C21 N30 N40 129.87(16) . . ?
N30 N40 H2N 102.4(18) . . ?
N30 N40 H1N 104(2) . . ?
H2N N40 H1N 111(3) . . ?
N60 C65 C64 123.8(2) . . ?
N60 C65 H65 118.1 . . ?
C64 C65 H65 118.1 . . ?
C54 C53 C52 119.5(2) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
N60 C61 C62 123.30(19) . . ?
N60 C61 C21 116.83(18) . . ?
C62 C61 C21 119.86(19) . . ?
C53 C54 C55 119.07(19) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
N4 C1 C2 118.07(19) . . ?
N4 C1 C3 118.65(19) . . ?
C2 C1 C3 123.2(2) . . ?
N50 C51 C52 122.95(18) . . ?
N50 C51 C11 111.61(16) . 3_665 ?
C52 C51 C11 125.44(18) . 3_665 ?
C61 C62 C63 118.1(2) . . ?
C61 C62 H62 120.9 . . ?
C63 C62 H62 120.9 . . ?
N20 C21 N30 109.98(16) . . ?
N20 C21 C61 124.03(18) . . ?
N30 C21 C61 125.98(18) . . ?
N10 C11 N30 109.08(16) . . ?
N10 C11 C51 120.48(17) . 3_665 ?
N30 C11 C51 130.44(17) . 3_665 ?
C51 C52 C53 118.13(19) . . ?
C51 C52 H52 120.9 . . ?
C53 C52 H52 120.9 . . ?
N50 C55 C54 122.39(19) . . ?
N50 C55 H55 118.8 . . ?
C54 C55 H55 118.8 . . ?
N2 C2 C1 179.6(3) . . ?
N3 C3 C1 178.8(3) . . ?
C65 C64 C63 118.7(2) . . ?
C65 C64 H64 120.6 . . ?
C63 C64 H64 120.6 . . ?
C64 C63 C62 119.1(2) . . ?
C64 C63 H63 120.4 . . ?
C62 C63 H63 120.4 . . ?

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
C54 H54 O3 0.95 2.44 3.380(3) 172.2 1_455
C52 H52 N40 0.95 2.45 3.063(3) 122.6 3_665
C64 H64 O2 0.95 2.60 3.301(3) 131.1 2_545
O1 H2O O3 0.84(3) 1.89(3) 2.719(2) 168(3) .
O1 H2O N4 0.84(3) 2.62(3) 3.423(2) 160(2) .
O1 H1O N2 0.80(3) 2.07(4) 2.873(3) 175(3) 2_645
N40 H2N N3 0.94(3) 2.36(3) 3.200(4) 149(2) 3_665
N40 H1N O2 0.91(4) 2.49(4) 3.204(3) 136(3) 2_645
N40 H1N N2 0.91(4) 2.54(3) 3.096(3) 120(3) 1_545

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1583583'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2017-12-18 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         'C30 H20 Co N18 O2'
_chemical_formula_sum            'C30 H20 Co N18 O2'
_chemical_formula_weight         723.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   9.0417(4)
_cell_length_b                   9.8054(4)
_cell_length_c                   9.8315(4)
_cell_angle_alpha                86.688(3)
_cell_angle_beta                 63.486(4)
_cell_angle_gamma                82.592(4)
_cell_volume                     773.45(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6407
_cell_measurement_theta_min      3.4730
_cell_measurement_theta_max      28.7610

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             369
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5440
_exptl_crystal_size_mid          0.2209
_exptl_crystal_size_min          0.1613
_exptl_absorpt_coefficient_mu    0.619
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3438
_diffrn_reflns_number            12862
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_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         3.096
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3212
_reflns_number_gt                2792
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.5862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3212
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.0000 0.5000 0.01940(11) Uani 1 2 d S . P . .
O1 O 0.65704(17) 0.04418(14) 0.27379(16) 0.0273(3) Uani 1 1 d . . . . .
N30 N 0.62836(19) -0.39821(15) 0.33682(17) 0.0178(3) Uani 1 1 d . . . . .
N50 N 0.29235(19) 0.11822(16) 0.48336(18) 0.0190(3) Uani 1 1 d . . . . .
N10 N 0.5040(2) -0.19292(16) 0.41455(19) 0.0212(3) Uani 1 1 d . . . . .
N40 N 0.7501(2) -0.51511(19) 0.3008(2) 0.0253(4) Uani 1 1 d . . . . .
N60 N 0.4946(2) -0.60720(16) 0.23958(18) 0.0204(3) Uani 1 1 d . . . . .
N20 N 0.4120(2) -0.25217(16) 0.35945(19) 0.0224(4) Uani 1 1 d . . . . .
N1 N 0.7663(2) 0.12984(18) 0.2316(2) 0.0264(4) Uani 1 1 d . . . . .
C62 C 0.3173(2) -0.4282(2) 0.1875(2) 0.0222(4) Uani 1 1 d . . . . .
H62 H 0.2760 -0.3335 0.1922 0.027 Uiso 1 1 calc R U . . .
C63 C 0.2651(2) -0.5234(2) 0.1249(2) 0.0252(4) Uani 1 1 d . . . . .
H63 H 0.1864 -0.4953 0.0866 0.030 Uiso 1 1 calc R U . . .
N3 N 1.0557(3) 0.3229(2) -0.0294(2) 0.0398(5) Uani 1 1 d . . . . .
C51 C 0.2482(2) 0.24540(19) 0.5462(2) 0.0186(4) Uani 1 1 d . . . . .
C64 C 0.3293(2) -0.6605(2) 0.1188(2) 0.0244(4) Uani 1 1 d . . . . .
H64 H 0.2961 -0.7279 0.0758 0.029 Uiso 1 1 calc R U . . .
C52 C 0.1096(2) 0.3298(2) 0.5533(2) 0.0236(4) Uani 1 1 d . . . . .
H52 H 0.0789 0.4172 0.6013 0.028 Uiso 1 1 calc R U . . .
C54 C 0.0645(2) 0.1560(2) 0.4192(2) 0.0246(4) Uani 1 1 d . . . . .
H54 H 0.0044 0.1237 0.3716 0.030 Uiso 1 1 calc R U . . .
C61 C 0.4320(2) -0.47442(19) 0.2435(2) 0.0186(4) Uani 1 1 d . . . . .
C11 C 0.6332(2) -0.28104(19) 0.4004(2) 0.0187(4) Uani 1 1 d . . . . .
C53 C 0.0165(2) 0.2832(2) 0.4881(2) 0.0255(4) Uani 1 1 d . . . . .
H53 H -0.0792 0.3386 0.4911 0.031 Uiso 1 1 calc R U . . .
C21 C 0.4897(2) -0.37589(19) 0.3113(2) 0.0193(4) Uani 1 1 d . . . . .
C65 C 0.4428(2) -0.6966(2) 0.1769(2) 0.0218(4) Uani 1 1 d . . . . .
H65 H 0.4867 -0.7906 0.1721 0.026 Uiso 1 1 calc R U . . .
N2 N 0.7779(3) 0.0233(3) -0.1047(3) 0.0593(7) Uani 1 1 d . . . . .
C1 C 0.8441(2) 0.1466(2) 0.0814(2) 0.0250(4) Uani 1 1 d . . . . .
C2 C 0.8082(3) 0.0774(2) -0.0226(3) 0.0327(5) Uani 1 1 d . . . . .
C55 C 0.2020(2) 0.0758(2) 0.4205(2) 0.0224(4) Uani 1 1 d . . . . .
H55 H 0.2332 -0.0128 0.3750 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9631(3) 0.2433(2) 0.0231(3) 0.0306(5) Uani 1 1 d . . . . .
H1N H 0.825(3) -0.501(2) 0.206(3) 0.033(7) Uiso 1 1 d . . . . .
H2N H 0.700(3) -0.586(3) 0.303(3) 0.041(7) 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 2.0923(14) . ?
Co1 O1 2.0923(14) 2_656 ?
Co1 N10 2.1035(16) 2_656 ?
Co1 N10 2.1035(16) . ?
Co1 N50 2.1416(15) 2_656 ?
Co1 N50 2.1416(15) . ?
O1 N1 1.289(2) . ?
N30 C11 1.354(2) . ?
N30 C21 1.373(2) . ?
N30 N40 1.423(2) . ?
N50 C55 1.339(2) . ?
N50 C51 1.355(2) . ?
N10 C11 1.319(2) . ?
N10 N20 1.373(2) . ?
N40 H1N 0.89(3) . ?
N40 H2N 0.87(3) . ?
N60 C65 1.340(2) . ?
N60 C61 1.347(2) . ?
N20 C21 1.319(2) . ?
N1 C1 1.333(3) . ?
C62 C63 1.383(3) . ?
C62 C61 1.395(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.387(3) . ?
C63 H63 0.9500 . ?
N3 C3 1.145(3) . ?
C51 C52 1.387(3) . ?
C51 C11 1.473(3) 2_656 ?
C64 C65 1.382(3) . ?
C64 H64 0.9500 . ?
C52 C53 1.394(3) . ?
C52 H52 0.9500 . ?
C54 C53 1.378(3) . ?
C54 C55 1.387(3) . ?
C54 H54 0.9500 . ?
C61 C21 1.471(3) . ?
C11 C51 1.473(3) 2_656 ?
C53 H53 0.9500 . ?
C65 H65 0.9500 . ?
N2 C2 1.137(3) . ?
C1 C3 1.427(3) . ?
C1 C2 1.430(3) . ?
C55 H55 0.9500 . ?

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 180.0 . 2_656 ?
O1 Co1 N10 95.34(6) . 2_656 ?
O1 Co1 N10 84.66(6) 2_656 2_656 ?
O1 Co1 N10 84.66(6) . . ?
O1 Co1 N10 95.34(6) 2_656 . ?
N10 Co1 N10 180.0 2_656 . ?
O1 Co1 N50 88.91(6) . 2_656 ?
O1 Co1 N50 91.09(6) 2_656 2_656 ?
N10 Co1 N50 102.77(6) 2_656 2_656 ?
N10 Co1 N50 77.23(6) . 2_656 ?
O1 Co1 N50 91.09(6) . . ?
O1 Co1 N50 88.91(6) 2_656 . ?
N10 Co1 N50 77.23(6) 2_656 . ?
N10 Co1 N50 102.77(6) . . ?
N50 Co1 N50 180.0 2_656 . ?
N1 O1 Co1 124.71(12) . . ?
C11 N30 C21 105.85(15) . . ?
C11 N30 N40 124.76(15) . . ?
C21 N30 N40 129.34(16) . . ?
C55 N50 C51 118.30(16) . . ?
C55 N50 Co1 125.68(13) . . ?
C51 N50 Co1 116.00(12) . . ?
C11 N10 N20 108.95(15) . . ?
C11 N10 Co1 113.84(12) . . ?
N20 N10 Co1 137.07(12) . . ?
N30 N40 H1N 105.3(16) . . ?
N30 N40 H2N 106.2(17) . . ?
H1N N40 H2N 110(2) . . ?
C65 N60 C61 116.90(16) . . ?
C21 N20 N10 106.47(15) . . ?
O1 N1 C1 113.48(17) . . ?
C63 C62 C61 118.36(18) . . ?
C63 C62 H62 120.8 . . ?
C61 C62 H62 120.8 . . ?
C62 C63 C64 119.17(18) . . ?
C62 C63 H63 120.4 . . ?
C64 C63 H63 120.4 . . ?
N50 C51 C52 122.42(17) . . ?
N50 C51 C11 111.76(16) . 2_656 ?
C52 C51 C11 125.80(17) . 2_656 ?
C65 C64 C63 118.35(18) . . ?
C65 C64 H64 120.8 . . ?
C63 C64 H64 120.8 . . ?
C51 C52 C53 118.28(18) . . ?
C51 C52 H52 120.9 . . ?
C53 C52 H52 120.9 . . ?
C53 C54 C55 118.92(18) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
N60 C61 C62 123.25(17) . . ?
N60 C61 C21 116.99(16) . . ?
C62 C61 C21 119.77(17) . . ?
N10 C11 N30 108.90(16) . . ?
N10 C11 C51 120.61(17) . 2_656 ?
N30 C11 C51 130.47(16) . 2_656 ?
C54 C53 C52 119.43(18) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
N20 C21 N30 109.82(16) . . ?
N20 C21 C61 124.15(16) . . ?
N30 C21 C61 126.02(16) . . ?
N60 C65 C64 123.98(18) . . ?
N60 C65 H65 118.0 . . ?
C64 C65 H65 118.0 . . ?
N1 C1 C3 117.97(19) . . ?
N1 C1 C2 123.2(2) . . ?
C3 C1 C2 118.76(19) . . ?
N2 C2 C1 179.2(3) . . ?
N50 C55 C54 122.58(18) . . ?
N50 C55 H55 118.7 . . ?
C54 C55 H55 118.7 . . ?
N3 C3 C1 176.4(2) . . ?

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
C52 H52 N40 0.95 2.46 3.080(3) 122.7 2_656
C65 H65 O1 0.95 2.56 3.349(2) 140.9 1_545
N40 H1N N3 0.89(3) 2.39(3) 3.137(3) 142(2) 2_755
N40 H2N N60 0.87(3) 2.24(3) 2.891(2) 131(2) .

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.058

