# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1_393K
_database_code_depnum_ccdc_archive 'CCDC 2264543'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'4(C1.5 Co0.25 N1.5), 0.04(H96 N24), 2(C3 H10 N O)'
_chemical_formula_sum            'C12 H24 Co N9 O2'
_chemical_formula_weight         385.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'y, -x+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'x, z+1/2, -y+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'x, -z+1/2, y+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'-z, y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'y+1/2, -x, z+1/2'
'-y+1/2, x, z+1/2'
'x+1/2, z, -y+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'y+1/2, -x+1/2, z'
'-y+1/2, x+1/2, z'
'x+1/2, z+1/2, -y'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'x+1/2, -z+1/2, y'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'-z, -x+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'y, -z+1/2, x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'-y, x+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'-x, -z+1/2, y+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-x, z+1/2, -y+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'z, -y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y, z+1/2'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x, y+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, -z, x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'-y+1/2, x, -z+1/2'
'y+1/2, -x, -z+1/2'
'-x+1/2, -z, y+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, -y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/2, y'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, -z+1/2, -x'
'y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'-y+1/2, x+1/2, -z'
'y+1/2, -x+1/2, -z'
'-x+1/2, -z+1/2, y'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-x+1/2, z+1/2, -y'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   12.4475(8)
_cell_length_b                   12.4475(8)
_cell_length_c                   12.4475(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1928.6(4)
_cell_formula_units_Z            3.99936
_cell_measurement_reflns_used    491
_cell_measurement_temperature    393(2)
_cell_measurement_theta_max      16.93
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0464 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.8670.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2082
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.954
_diffrn_reflns_theta_min         2.834
_diffrn_ambient_temperature      393
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                94
_reflns_number_total             129
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.160
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     30
_refine_ls_number_reflns         129
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.233
_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)+(0.0744P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-C4
 2.45 with sigma of 0.02
 N2-O1
 1.422 with sigma of 0.002
 O1-N2
 1.42 with sigma of 0.02
 O1-C4
 2.36 with sigma of 0.02
 O1-C2
 2.36 with sigma of 0.02
 C4-C3
 2.45 with sigma of 0.02
 C3-C2
 2.45 with sigma of 0.02
 N2-C4 = N2-C3 = N2-C2
 1.48 with sigma of 0.02
 O1-C3
 2.36 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(O1) = Uanis(N2) = Uanis(C4) = Uanis(C2)
4. Others
 Fixed Sof: H1C(0.02083) H1B(0.02083) H1A(0.02083) H1D(0.02083) N2(0.04167)
 C2(0.04167) H2A(0.04167) H2B(0.04167) H2C(0.04167) C3(0.04167) H3A(0.04167)
 H3B(0.04167) H3C(0.04167) C4(0.04167) H4A(0.04167) H4B(0.04167) H4C(0.04167)
 O1(0.04167) H1(0.04167)
5.a Riding coordinates:
 N1(H1C,H1B,H1A), N1(H1D), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C),
 O1(H1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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 0.0000 1.0000 1.0000 0.1088(13) Uani 1 48 d S T P . .
C1 C 0.0000 1.0000 0.8482(8) 0.124(2) Uani 1 8 d S T P . .
N3 N 0.0000 1.0000 0.7521(5) 0.165(3) Uani 1 8 d S T P . .
N1 N 0.0000 1.0000 0.5000 0.178(9) Uani 1 48 d S T P . .
H1C H -0.0238 1.0000 0.5674 0.266 Uiso 0.0417 2 d RS T P . .
H1B H -0.0238 1.0584 0.4762 0.266 Uiso 0.0417 2 d RS T P . .
H1A H -0.0238 0.9416 0.4762 0.266 Uiso 0.0417 2 d RS T P . .
H1D H 0.0731 1.0000 0.5000 0.266 Uiso 0.1666 8 d RS T P . .
N2 N 0.261(2) 0.768(3) 0.753(4) 0.108(7) Uani 0.0417 1 d D . . A -1
C2 C 0.283(4) 0.751(3) 0.636(3) 0.108(7) Uani 0.0417 1 d D . . A -1
H2A H 0.3104 0.8172 0.6089 0.163 Uiso 0.0417 1 d R . . A -1
H2B H 0.2219 0.7288 0.5943 0.163 Uiso 0.0417 1 d R . . A -1
H2C H 0.3376 0.6965 0.6321 0.163 Uiso 0.0417 1 d R . . A -1
C3 C 0.176(3) 0.852(4) 0.768(4) 0.108(7) Uani 0.0417 1 d D . . A -1
H3A H 0.1098 0.8127 0.7663 0.163 Uiso 0.0417 1 d R . . A -1
H3B H 0.1792 0.9004 0.7083 0.163 Uiso 0.0417 1 d R . . A -1
H3C H 0.1814 0.8912 0.8339 0.163 Uiso 0.0417 1 d R . . A -1
C4 C 0.229(3) 0.666(3) 0.806(5) 0.108(7) Uani 0.0417 1 d D . . A -1
H4A H 0.2692 0.6552 0.8710 0.163 Uiso 0.0417 1 d R . . A -1
H4B H 0.2444 0.6089 0.7565 0.163 Uiso 0.0417 1 d R . . A -1
H4C H 0.1532 0.6651 0.8228 0.163 Uiso 0.0417 1 d R . . A -1
O1 O 0.357(2) 0.806(3) 0.802(3) 0.108(7) Uani 0.0417 1 d D . . A -1
H1 H 0.3403 0.8495 0.8478 0.163 Uiso 0.0417 1 d R . . A -1


_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 C1 1.889(10) 105_676 ?
Co1 C1 1.889(10) 97_577 ?
Co1 C1 1.889(10) 9_456 ?
Co1 C1 1.889(10) 101_667 ?
Co1 C1 1.889(10) 5_465 ?
Co1 C1 1.889(10) . ?
C1 N3 1.197(10) . ?
N2 C2 1.494(19) . ?
N2 C3 1.494(19) . ?
N2 C4 1.490(19) . ?
N2 O1 1.422(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
C1 Co1 C1 180.0 105_676 9_456 ?
C1 Co1 C1 180.0 5_465 101_667 ?
C1 Co1 C1 90.000(5) 105_676 101_667 ?
C1 Co1 C1 90.000(4) 97_577 101_667 ?
C1 Co1 C1 90.000(5) 97_577 5_465 ?
C1 Co1 C1 90.000(2) 5_465 . ?
C1 Co1 C1 90.000(3) 105_676 5_465 ?
C1 Co1 C1 90.000(1) 105_676 97_577 ?
C1 Co1 C1 90.000(5) 9_456 5_465 ?
C1 Co1 C1 90.000(1) 9_456 . ?
C1 Co1 C1 90.000(2) 101_667 . ?
C1 Co1 C1 90.000(1) 9_456 97_577 ?
C1 Co1 C1 90.000(1) 105_676 . ?
C1 Co1 C1 90.000(1) 9_456 101_667 ?
C1 Co1 C1 180.0 97_577 . ?
N3 C1 Co1 180.0 . . ?
C3 N2 C2 110.5(17) . . ?
C4 N2 C2 111.1(17) . . ?
C4 N2 C3 110.5(17) . . ?
O1 N2 C2 108.0(17) . . ?
O1 N2 C3 108.0(17) . . ?
O1 N2 C4 108.7(17) . . ?

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
N1 H1C N3 0.89 2.32 3.138(7) 153.2 .
N1 H1D N3 0.91 2.23 3.138(7) 180.0 53_464

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

data_1_298K
_database_code_depnum_ccdc_archive 'CCDC 2264544'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 Co N6, 2(C3 H10 N O), H4 N'
_chemical_formula_sum            'C12 H24 Co N9 O2'
_chemical_formula_weight         385.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.481(2)
_cell_length_b                   9.175(3)
_cell_length_c                   12.439(3)
_cell_angle_alpha                88.801(7)
_cell_angle_beta                 88.422(7)
_cell_angle_gamma                83.065(7)
_cell_volume                     960.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5892
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.758
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.9387.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20898
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.686
_diffrn_reflns_theta_min         1.638
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3965
_reflns_number_total             5348
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.277
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N7(H7D,H7E,H7F), N7(H7G)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C7(H7A,H7B,H7C),
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.79322(2) 0.75496(2) 0.25424(2) 0.02595(7) Uani 1 1 d . . . . .
O1 O 0.54065(13) 0.31676(14) 0.06893(11) 0.0461(3) Uani 1 1 d . . . . .
H1 H 0.5423 0.3822 0.1126 0.069 Uiso 1 1 calc GR . . . .
N7 N 0.23192(15) 0.20433(14) 0.21970(11) 0.0335(3) Uani 1 1 d . . . . .
H7D H 0.2382 0.2101 0.1482 0.040 Uiso 1 1 d R . . . .
H7E H 0.1905 0.2908 0.2455 0.040 Uiso 1 1 d R . . . .
H7F H 0.3286 0.1803 0.2455 0.040 Uiso 1 1 d R . . . .
H7G H 0.1689 0.1346 0.2401 0.040 Uiso 1 1 d R . . . .
N8 N 0.29374(16) 0.73982(15) 0.50580(11) 0.0344(3) Uani 1 1 d . . . . .
N1 N 1.02645(18) 0.97725(17) 0.28608(13) 0.0449(4) Uani 1 1 d . . . . .
N9 N 0.69705(17) 0.27232(15) 0.02974(12) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.41152(17) 0.68282(19) 0.57926(12) 0.0615(4) Uani 1 1 d . . . . .
H2 H 0.4975 0.7079 0.5598 0.092 Uiso 1 1 calc GR . . . .
N4 N 1.05633(17) 0.49689(16) 0.25963(13) 0.0421(4) Uani 1 1 d . . . . .
N2 N 0.51991(17) 1.00226(16) 0.25034(12) 0.0417(4) Uani 1 1 d . . . . .
N5 N 0.56823(19) 0.53425(17) 0.20387(12) 0.0424(4) Uani 1 1 d . . . . .
N3 N 0.83650(19) 0.79075(18) 0.01195(13) 0.0457(4) Uani 1 1 d . . . . .
N6 N 0.71203(19) 0.72585(17) 0.49322(12) 0.0453(4) Uani 1 1 d . . . . .
C2 C 0.62287(18) 0.90987(16) 0.25091(12) 0.0278(3) Uani 1 1 d . . . . .
C4 C 0.95958(18) 0.59540(17) 0.25797(13) 0.0300(3) Uani 1 1 d . . . . .
C1 C 0.93967(19) 0.89233(17) 0.27601(13) 0.0305(4) Uani 1 1 d . . . . .
C3 C 0.82333(18) 0.77761(17) 0.10350(14) 0.0314(4) Uani 1 1 d . . . . .
C6 C 0.74986(18) 0.73481(16) 0.40422(14) 0.0301(3) Uani 1 1 d . . . . .
C5 C 0.65160(19) 0.61793(17) 0.22531(12) 0.0299(3) Uani 1 1 d . . . . .
C10 C 0.7989(2) 0.2198(2) 0.12108(17) 0.0542(5) Uani 1 1 d . . . . .
H10A H 0.8151 0.3014 0.1648 0.081 Uiso 1 1 calc GR . . . .
H10B H 0.8997 0.1743 0.0939 0.081 Uiso 1 1 calc GR . . . .
H10C H 0.7480 0.1495 0.1636 0.081 Uiso 1 1 calc GR . . . .
C8 C 0.2966(3) 0.9004(2) 0.49415(18) 0.0550(5) Uani 1 1 d . . . . .
H8A H 0.2876 0.9438 0.5639 0.082 Uiso 1 1 calc GR . . . .
H8B H 0.2093 0.9418 0.4514 0.082 Uiso 1 1 calc GR . . . .
H8C H 0.3948 0.9196 0.4596 0.082 Uiso 1 1 calc GR . . . .
C11 C 0.7595(3) 0.3968(2) -0.02817(18) 0.0575(6) Uani 1 1 d . . . . .
H11A H 0.6915 0.4289 -0.0867 0.086 Uiso 1 1 calc GR . . . .
H11B H 0.8648 0.3658 -0.0558 0.086 Uiso 1 1 calc GR . . . .
H11C H 0.7626 0.4763 0.0204 0.086 Uiso 1 1 calc GR . . . .
C7 C 0.3240(3) 0.6674(3) 0.40136(17) 0.0615(6) Uani 1 1 d . . . . .
H7A H 0.4242 0.6893 0.3715 0.092 Uiso 1 1 calc GR . . . .
H7B H 0.2408 0.7024 0.3531 0.092 Uiso 1 1 calc GR . . . .
H7C H 0.3267 0.5631 0.4115 0.092 Uiso 1 1 calc GR . . . .
C9 C 0.1422(3) 0.7045(3) 0.5558(2) 0.0736(7) Uani 1 1 d . . . . .
H9A H 0.1453 0.5999 0.5642 0.110 Uiso 1 1 calc GR . . . .
H9B H 0.0559 0.7413 0.5105 0.110 Uiso 1 1 calc GR . . . .
H9C H 0.1271 0.7493 0.6249 0.110 Uiso 1 1 calc GR . . . .
C12 C 0.6788(3) 0.1505(3) -0.0441(2) 0.0804(8) Uani 1 1 d . . . . .
H12A H 0.6433 0.0698 -0.0037 0.121 Uiso 1 1 calc GR . . . .
H12B H 0.7792 0.1191 -0.0789 0.121 Uiso 1 1 calc GR . . . .
H12C H 0.6022 0.1840 -0.0973 0.121 Uiso 1 1 calc GR . . . .


_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 C2 1.9010(15) . ?
Co1 C4 1.9073(16) . ?
Co1 C1 1.9013(18) . ?
Co1 C3 1.8958(18) . ?
Co1 C6 1.9010(18) . ?
Co1 C5 1.8869(18) . ?
O1 H1 0.8200 . ?
O1 N9 1.4161(18) . ?
N7 H7D 0.8900 . ?
N7 H7E 0.8900 . ?
N7 H7F 0.8900 . ?
N7 H7G 0.9100 . ?
N8 O2 1.4178(18) . ?
N8 C8 1.480(2) . ?
N8 C7 1.474(2) . ?
N8 C9 1.480(3) . ?
N1 C1 1.145(2) . ?
N9 C10 1.483(2) . ?
N9 C11 1.481(2) . ?
N9 C12 1.486(2) . ?
O2 H2 0.8200 . ?
N4 C4 1.1453(19) . ?
N2 C2 1.1412(19) . ?
N5 C5 1.145(2) . ?
N3 C3 1.146(2) . ?
N6 C6 1.148(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C2 Co1 C4 178.28(7) . . ?
C2 Co1 C1 90.41(7) . . ?
C2 Co1 C6 87.74(6) . . ?
C1 Co1 C4 91.27(7) . . ?
C3 Co1 C2 89.52(7) . . ?
C3 Co1 C4 90.88(7) . . ?
C3 Co1 C1 89.51(7) . . ?
C3 Co1 C6 176.60(6) . . ?
C6 Co1 C4 91.79(7) . . ?
C6 Co1 C1 92.52(7) . . ?
C5 Co1 C2 90.28(7) . . ?
C5 Co1 C4 88.06(7) . . ?
C5 Co1 C1 177.09(7) . . ?
C5 Co1 C3 87.67(7) . . ?
C5 Co1 C6 90.33(7) . . ?
N9 O1 H1 109.5 . . ?
H7D N7 H7E 109.5 . . ?
H7D N7 H7F 109.5 . . ?
H7D N7 H7G 109.5 . . ?
H7E N7 H7F 109.5 . . ?
H7E N7 H7G 109.5 . . ?
H7F N7 H7G 109.5 . . ?
O2 N8 C8 108.79(14) . . ?
O2 N8 C7 109.77(15) . . ?
O2 N8 C9 104.70(15) . . ?
C8 N8 C9 111.50(17) . . ?
C7 N8 C8 110.98(16) . . ?
C7 N8 C9 110.89(17) . . ?
O1 N9 C10 109.30(14) . . ?
O1 N9 C11 109.66(13) . . ?
O1 N9 C12 104.16(15) . . ?
C10 N9 C12 110.98(16) . . ?
C11 N9 C10 111.06(15) . . ?
C11 N9 C12 111.44(18) . . ?
N8 O2 H2 109.5 . . ?
N2 C2 Co1 179.03(16) . . ?
N4 C4 Co1 178.03(15) . . ?
N1 C1 Co1 177.81(15) . . ?
N3 C3 Co1 177.80(15) . . ?
N6 C6 Co1 174.91(14) . . ?
N5 C5 Co1 177.37(15) . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N8 C8 H8A 109.5 . . ?
N8 C8 H8B 109.5 . . ?
N8 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N9 C11 H11A 109.5 . . ?
N9 C11 H11B 109.5 . . ?
N9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C7 H7A 109.5 . . ?
N8 C7 H7B 109.5 . . ?
N8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N8 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
N8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N9 C12 H12A 109.5 . . ?
N9 C12 H12B 109.5 . . ?
N9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
O1 H1 N5 0.82 1.85 2.670(2) 173.3 .
N7 H7D N3 0.89 2.11 2.953(2) 158.3 2_665
N7 H7E N4 0.89 2.09 2.953(2) 161.8 1_455
N7 H7F N2 0.89 2.16 2.9114(19) 141.8 1_545
N7 H7G N1 0.91 2.05 2.964(2) 180.0 1_445
O2 H2 N6 0.82 2.00 2.806(2) 166.7 .

_olex2_submission_special_instructions 'No special instructions were received'
