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

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

data_LIGAND
_database_code_depnum_ccdc_archive 'CCDC 1890132'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Zhang'
;Soochow University
China
;

_audit_update_record             
;
2019-01-11 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H34 N8 O4, 2(C H4 O)'
_chemical_formula_sum            'C46 H42 N8 O6'
_chemical_formula_weight         802.87

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'

_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                   12.6245(12)
_cell_length_b                   8.6062(9)
_cell_length_c                   18.1703(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.732(3)
_cell_angle_gamma                90
_cell_volume                     1956.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4553
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      24.27
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
 Sheldrick, G.M. SADABS (Program for Scaling and Correction of Area Detector
 Data), version 2008/1; University of Göttingen: Göttingen, Germany, 2008.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24198
_diffrn_reflns_av_unetI/netI     0.1301
_diffrn_reflns_av_R_equivalents  0.1501
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4634
_reflns_number_gt                2426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker D8 Quest'
_computing_cell_refinement       'Bruker D8 Quest'
_computing_data_reduction        'Bruker D8 Quest'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+1.4115P] 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         4634
_refine_ls_number_parameters     287
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1706
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.35478(19) 0.4497(3) 0.51744(12) 0.0521(7) Uani 1 1 d D . . . .
H1O1 H 0.415(2) 0.486(4) 0.5421(18) 0.063 Uiso 1 1 d D U . . .
O2 O -0.23994(19) 0.8877(3) -0.12858(13) 0.0555(7) Uani 1 1 d D . . . .
H1O2 H -0.263(3) 0.895(5) -0.0867(13) 0.067 Uiso 1 1 d D U . . .
O3 O 0.0515(3) 1.2896(3) -0.12308(19) 0.0783(9) Uani 1 1 d D . . . .
H1O3 H 0.053(4) 1.187(2) -0.120(3) 0.094 Uiso 1 1 d D U . . .
N1 N 0.4729(2) 0.4445(3) 0.38995(13) 0.0387(7) Uani 1 1 d . . . . .
N2 N 0.0434(2) 0.9681(3) -0.09686(14) 0.0386(7) Uani 1 1 d . . . . .
N3 N 0.58400(18) 0.4120(3) 0.09431(12) 0.0256(6) Uani 1 1 d D . . . .
H1N3 H 0.554(4) 0.451(6) 0.0512(18) 0.031 Uiso 0.5 1 d D U P . .
N4 N 0.37245(19) 0.5436(3) 0.05924(12) 0.0258(6) Uani 1 1 d D . . . .
H1N4 H 0.425(3) 0.518(7) 0.033(3) 0.031 Uiso 0.5 1 d D U P . .
C1 C 0.3789(3) 0.3147(4) 0.48086(17) 0.0491(9) Uani 1 1 d . . . . .
H1A H 0.321530 0.240107 0.482090 0.059 Uiso 1 1 calc R U . . .
H1B H 0.443820 0.269345 0.506675 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3938(3) 0.3459(4) 0.40097(16) 0.0354(8) Uani 1 1 d . . . . .
C3 C 0.3303(3) 0.2761(4) 0.34321(17) 0.0373(8) Uani 1 1 d . . . . .
H3 H 0.275746 0.209048 0.352279 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3484(3) 0.3066(4) 0.27162(16) 0.0359(8) Uani 1 1 d . . . . .
H4 H 0.306485 0.258805 0.232021 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4289(2) 0.4083(3) 0.25819(15) 0.0277(7) Uani 1 1 d . . . . .
C6 C 0.4882(2) 0.4753(4) 0.31991(15) 0.0350(8) Uani 1 1 d . . . . .
H6 H 0.541644 0.545491 0.312219 0.042 Uiso 1 1 calc R U . . .
C7 C -0.1488(3) 0.9782(4) -0.1211(2) 0.0473(9) Uani 1 1 d . . . . .
H7A H -0.154361 1.056824 -0.083557 0.057 Uiso 1 1 calc R U . . .
H7B H -0.144358 1.031162 -0.167731 0.057 Uiso 1 1 calc R U . . .
C8 C -0.0472(2) 0.8854(4) -0.09968(15) 0.0323(7) Uani 1 1 d . . . . .
C9 C -0.0475(2) 0.7306(4) -0.08490(18) 0.0391(8) Uani 1 1 d . . . . .
H9 H -0.111876 0.677300 -0.087000 0.047 Uiso 1 1 calc R U . . .
C10 C 0.0483(2) 0.6524(4) -0.06672(17) 0.0378(8) Uani 1 1 d . . . . .
H10 H 0.048775 0.546182 -0.057150 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1431(2) 0.7339(3) -0.06296(14) 0.0254(7) Uani 1 1 d . . . . .
C12 C 0.1356(2) 0.8917(4) -0.07845(17) 0.0356(8) Uani 1 1 d . . . . .
H12 H 0.198844 0.948138 -0.075895 0.043 Uiso 1 1 calc R U . . .
C13 C 0.6855(2) 0.3534(3) 0.10064(15) 0.0258(7) Uani 1 1 d . . . . .
C14 C 0.7190(2) 0.3053(4) 0.17620(15) 0.0349(8) Uani 1 1 d . . . . .
H14 H 0.785087 0.263670 0.194992 0.042 Uiso 1 1 calc R U . . .
C15 C 0.6372(2) 0.3318(4) 0.21413(16) 0.0350(8) Uani 1 1 d . . . . .
H15 H 0.635253 0.310868 0.264151 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5521(2) 0.3993(3) 0.16263(14) 0.0268(7) Uani 1 1 d . . . . .
C17 C 0.4512(2) 0.4415(3) 0.18138(14) 0.0257(6) Uani 1 1 d . . . . .
C18 C 0.3693(2) 0.5092(3) 0.13249(15) 0.0253(7) Uani 1 1 d . . . . .
C19 C 0.2674(2) 0.5581(3) 0.14978(15) 0.0283(7) Uani 1 1 d . . . . .
H19 H 0.243516 0.549412 0.195853 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2115(2) 0.6190(3) 0.08783(15) 0.0273(7) Uani 1 1 d . . . . .
H20 H 0.142624 0.659347 0.083691 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2775(2) 0.6101(3) 0.02962(15) 0.0253(6) Uani 1 1 d . . . . .
C22 C 0.2498(2) 0.6594(3) -0.04384(15) 0.0253(7) Uani 1 1 d . . . . .
C23 C 0.0334(4) 1.3123(7) -0.2009(3) 0.0924(16) Uani 1 1 d . . . . .
H23A H 0.060752 1.412042 -0.212751 0.139 Uiso 1 1 calc R U . . .
H23B H -0.041893 1.307988 -0.217794 0.139 Uiso 1 1 calc R U . . .
H23C H 0.069237 1.232384 -0.224943 0.139 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.393(4) . ?
O1 H1O1 0.884(18) . ?
O2 C7 1.381(4) . ?
O2 H1O2 0.851(18) . ?
O3 C23 1.415(5) . ?
O3 H1O3 0.884(19) . ?
N1 C6 1.339(4) . ?
N1 C2 1.345(4) . ?
N2 C12 1.340(4) . ?
N2 C8 1.342(4) . ?
N3 C16 1.360(3) . ?
N3 C13 1.367(4) . ?
N3 H1N3 0.89(2) . ?
N4 C18 1.370(3) . ?
N4 C21 1.372(4) . ?
N4 H1N4 0.90(2) . ?
C1 C2 1.513(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.371(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(4) . ?
C5 C17 1.488(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.517(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.359(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(4) . ?
C11 C22 1.490(4) . ?
C12 H12 0.9300 . ?
C13 C22 1.405(4) 3_665 ?
C13 C14 1.442(4) . ?
C14 C15 1.336(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.448(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.410(4) . ?
C17 C18 1.397(4) . ?
C18 C19 1.428(4) . ?
C19 C20 1.351(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.433(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 O1 H1O1 108(3) . . ?
C7 O2 H1O2 104(3) . . ?
C23 O3 H1O3 102(3) . . ?
C6 N1 C2 118.1(3) . . ?
C12 N2 C8 117.2(3) . . ?
C16 N3 C13 106.4(2) . . ?
C16 N3 H1N3 134(4) . . ?
C13 N3 H1N3 120(4) . . ?
C18 N4 C21 109.5(2) . . ?
C18 N4 H1N4 126(4) . . ?
C21 N4 H1N4 124(4) . . ?
O1 C1 C2 111.9(3) . . ?
O1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C3 122.1(3) . . ?
N1 C2 C1 116.5(3) . . ?
C3 C2 C1 121.4(3) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 116.6(3) . . ?
C6 C5 C17 121.9(3) . . ?
C4 C5 C17 121.4(3) . . ?
N1 C6 C5 123.7(3) . . ?
N1 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
O2 C7 C8 113.1(3) . . ?
O2 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 C9 122.5(3) . . ?
N2 C8 C7 114.7(3) . . ?
C9 C8 C7 122.9(3) . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 117.0(3) . . ?
C10 C11 C22 122.9(3) . . ?
C12 C11 C22 120.2(3) . . ?
N2 C12 C11 124.3(3) . . ?
N2 C12 H12 117.8 . . ?
C11 C12 H12 117.8 . . ?
N3 C13 C22 126.8(2) . 3_665 ?
N3 C13 C14 109.7(2) . . ?
C22 C13 C14 123.5(3) 3_665 . ?
C15 C14 C13 107.1(3) . . ?
C15 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
C14 C15 C16 107.0(3) . . ?
C14 C15 H15 126.5 . . ?
C16 C15 H15 126.5 . . ?
N3 C16 C17 126.0(2) . . ?
N3 C16 C15 109.7(2) . . ?
C17 C16 C15 124.3(2) . . ?
C18 C17 C16 124.7(2) . . ?
C18 C17 C5 117.3(2) . . ?
C16 C17 C5 117.9(2) . . ?
N4 C18 C17 126.3(3) . . ?
N4 C18 C19 107.2(2) . . ?
C17 C18 C19 126.5(2) . . ?
C20 C19 C18 108.4(2) . . ?
C20 C19 H19 125.8 . . ?
C18 C19 H19 125.8 . . ?
C19 C20 C21 107.7(3) . . ?
C19 C20 H20 126.1 . . ?
C21 C20 H20 126.1 . . ?
N4 C21 C22 126.4(2) . . ?
N4 C21 C20 107.3(2) . . ?
C22 C21 C20 126.3(3) . . ?
C21 C22 C13 125.6(3) . 3_665 ?
C21 C22 C11 117.1(2) . . ?
C13 C22 C11 117.4(2) 3_665 . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 H1O1 N1 0.884(18) 1.85(2) 2.722(4) 169(4) 3_666
O2 H1O2 O1 0.851(18) 1.88(2) 2.693(3) 158(4) 2
O3 H1O3 N2 0.884(19) 1.94(2) 2.812(4) 170(4) .
N3 H1N3 N4 0.89(2) 2.45(5) 2.892(3) 111(4) .
N3 H1N3 N4 0.89(2) 2.32(5) 2.940(3) 127(5) 3_665
N4 H1N4 N3 0.90(2) 2.35(5) 2.892(3) 119(4) .
N4 H1N4 N3 0.90(2) 2.37(5) 2.940(3) 122(4) 3_665
C12 H12 O1 0.93 2.57 3.355(4) 141.8 4_575

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_CO-THPP
_database_code_depnum_ccdc_archive 'CCDC 1890133'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Zhang'
;Soochow University
China
;
_audit_update_record             
;
2019-01-11 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H32 Co N8 O4'
_chemical_formula_weight         795.70

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.8838(9)
_cell_length_b                   9.1130(7)
_cell_length_c                   20.2408(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.771(3)
_cell_angle_gamma                90
_cell_volume                     1770.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7716
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.46

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             822
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.545
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
; 
 Sheldrick, G.M. SADABS (Program for Scaling and Correction of Area Detector 
 Data), version 2008/1; University of Göttingen: Göttingen, Germany, 2008. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44066
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.463
_diffrn_reflns_theta_max         28.260
_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             4369
_reflns_number_gt                2673
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+4.4967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4369
_refine_ls_number_parameters     259
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 1.000000 1.000000 0.000000 0.0251(2) Uani 1 2 d S . P . .
N1 N 1.0996(3) 0.8247(3) 0.04438(14) 0.0270(7) Uani 1 1 d . . . . .
N2 N 0.9571(3) 1.0588(3) 0.08754(14) 0.0278(7) Uani 1 1 d . . . . .
N3 N 1.0399(4) 0.6382(5) 0.31356(18) 0.0496(10) Uani 1 1 d . . . . .
C13 C 1.3958(5) 0.4460(7) -0.1225(2) 0.0570(14) Uani 1 1 d . . . . .
H13 H 1.471110 0.445917 -0.144231 0.068 Uiso 1 1 calc R U . . .
C1 C 0.8904(4) 1.1843(4) 0.10101(18) 0.0312(9) Uani 1 1 d . . . . .
C2 C 0.8900(5) 1.1924(5) 0.17214(19) 0.0415(11) Uani 1 1 d . . . . .
H2 H 0.851557 1.268501 0.194051 0.050 Uiso 1 1 calc R U . . .
C3 C 0.9553(5) 1.0700(5) 0.2014(2) 0.0426(11) Uani 1 1 d . . . . .
H3 H 0.970067 1.043011 0.247936 0.051 Uiso 1 1 calc R U . . .
C4 C 0.9979(4) 0.9887(4) 0.14946(17) 0.0306(8) Uani 1 1 d . . . . .
C5 C 1.0749(4) 0.8600(4) 0.16147(18) 0.0298(8) Uani 1 1 d . . . . .
C6 C 1.1242(4) 0.7862(4) 0.11223(17) 0.0284(8) Uani 1 1 d . . . . .
C7 C 1.2072(5) 0.6568(4) 0.12522(19) 0.0380(10) Uani 1 1 d . . . . .
H7 H 1.238809 0.609688 0.167976 0.046 Uiso 1 1 calc R U . . .
C8 C 1.2323(5) 0.6139(4) 0.0658(2) 0.0388(10) Uani 1 1 d . . . . .
H8 H 1.285085 0.530785 0.058646 0.047 Uiso 1 1 calc R U . . .
C9 C 1.1641(4) 0.7176(4) 0.01511(18) 0.0285(8) Uani 1 1 d . . . . .
C10 C 1.1663(4) 0.7089(4) -0.05342(18) 0.0294(8) Uani 1 1 d . . . . .
C11 C 1.2301(4) 0.5747(4) -0.07575(18) 0.0315(9) Uani 1 1 d . . . . .
C12 C 1.1784(5) 0.4388(4) -0.0642(2) 0.0414(10) Uani 1 1 d . . . . .
H12 H 1.099059 0.436310 -0.045401 0.050 Uiso 1 1 calc R U . . .
N4 N 1.2315(4) 0.3111(4) -0.0775(2) 0.0535(11) Uani 1 1 d . . . . .
C14 C 1.3385(6) 0.3160(6) -0.1076(2) 0.0563(14) Uani 1 1 d . . . . .
C15 C 1.3896(8) 0.1588(9) -0.1194(3) 0.104(3) Uani 1 1 d . . . . .
H15A H 1.461718 0.126935 -0.079173 0.125 Uiso 1 1 calc R U . . .
H15B H 1.310744 0.088932 -0.126157 0.125 Uiso 1 1 calc R U . . .
C16 C 1.3420(5) 0.5764(5) -0.1054(2) 0.0458(11) Uani 1 1 d . . . . .
H16 H 1.381970 0.667163 -0.113924 0.055 Uiso 1 1 calc R U . . .
C17 C 1.1076(4) 0.7963(4) 0.23199(17) 0.0295(8) Uani 1 1 d . . . . .
C18 C 1.2299(5) 0.8269(4) 0.27874(19) 0.0374(9) Uani 1 1 d . . . . .
H18 H 1.297543 0.888832 0.266738 0.045 Uiso 1 1 calc R U . . .
C19 C 1.2541(4) 0.7670(4) 0.34354(19) 0.0364(9) Uani 1 1 d . . . . .
H19 H 1.337218 0.789703 0.376541 0.044 Uiso 1 1 calc R U . . .
C20 C 1.1578(4) 0.6755(4) 0.35937(18) 0.0307(8) Uani 1 1 d . . . . .
C21 C 1.1756(5) 0.6036(5) 0.4284(2) 0.0396(10) Uani 1 1 d . . . . .
H21A H 1.099897 0.636032 0.449399 0.048 Uiso 1 1 calc R U . . .
H21B H 1.168941 0.495687 0.422731 0.048 Uiso 1 1 calc R U . . .
C22 C 1.0167(5) 0.7005(5) 0.2518(2) 0.0477(12) Uani 1 1 d . . . . .
H22 H 0.932359 0.677275 0.219813 0.057 Uiso 1 1 calc R U . . .
O1 O 1.4399(7) 0.1598(6) -0.1719(3) 0.126(2) Uani 1 1 d D . . . .
H1A H 1.467995 0.075246 -0.175947 0.152 Uiso 1 1 d DR U . . .
O2 O 1.3060(3) 0.6406(3) 0.47149(14) 0.0465(8) Uani 1 1 d D . . . .
H2A H 1.296813 0.673947 0.508338 0.056 Uiso 1 1 d DR U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 1.977(3) . ?
Co1 N1 1.977(3) 3_775 ?
Co1 N2 1.991(3) . ?
Co1 N2 1.991(3) 3_775 ?
Co1 O2 2.264(3) 4_575 ?
Co1 O2 2.264(3) 2_755 ?
N1 C9 1.375(5) . ?
N1 C6 1.382(4) . ?
N2 C4 1.379(4) . ?
N2 C1 1.379(5) . ?
N3 C22 1.341(5) . ?
N3 C20 1.349(5) . ?
C13 C14 1.378(8) . ?
C13 C16 1.380(7) . ?
C1 C10 1.390(5) 3_775 ?
C1 C2 1.443(5) . ?
C2 C3 1.353(6) . ?
C3 C4 1.429(5) . ?
C4 C5 1.388(5) . ?
C5 C6 1.384(5) . ?
C5 C17 1.503(5) . ?
C6 C7 1.424(5) . ?
C7 C8 1.342(6) . ?
C8 C9 1.440(5) . ?
C9 C10 1.395(5) . ?
C10 C11 1.495(5) . ?
C11 C16 1.378(6) . ?
C11 C12 1.381(6) . ?
C12 N4 1.330(5) . ?
N4 C14 1.341(7) . ?
C14 C15 1.556(8) . ?
C15 O1 1.276(8) . ?
C17 C18 1.374(5) . ?
C17 C22 1.379(6) . ?
C18 C19 1.388(5) . ?
C19 C20 1.360(6) . ?
C20 C21 1.515(5) . ?
C21 O2 1.415(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N1 180.0 . 3_775 ?
N1 Co1 N2 90.09(12) . . ?
N1 Co1 N2 89.91(12) 3_775 . ?
N1 Co1 N2 89.91(12) . 3_775 ?
N1 Co1 N2 90.09(12) 3_775 3_775 ?
N2 Co1 N2 180.0 . 3_775 ?
N1 Co1 O2 87.62(12) . 4_575 ?
N1 Co1 O2 92.38(12) 3_775 4_575 ?
N2 Co1 O2 91.86(12) . 4_575 ?
N2 Co1 O2 88.14(12) 3_775 4_575 ?
N1 Co1 O2 92.38(12) . 2_755 ?
N1 Co1 O2 87.62(12) 3_775 2_755 ?
N2 Co1 O2 88.14(12) . 2_755 ?
N2 Co1 O2 91.86(12) 3_775 2_755 ?
O2 Co1 O2 180.0 4_575 2_755 ?
C9 N1 C6 104.9(3) . . ?
C9 N1 Co1 127.6(2) . . ?
C6 N1 Co1 127.4(2) . . ?
C4 N2 C1 104.7(3) . . ?
C4 N2 Co1 127.3(2) . . ?
C1 N2 Co1 127.8(2) . . ?
C22 N3 C20 117.5(4) . . ?
C14 C13 C16 118.8(4) . . ?
N2 C1 C10 125.2(3) . 3_775 ?
N2 C1 C2 110.8(3) . . ?
C10 C1 C2 124.0(3) 3_775 . ?
C3 C2 C1 106.3(3) . . ?
C2 C3 C4 107.3(3) . . ?
N2 C4 C5 125.5(3) . . ?
N2 C4 C3 110.8(3) . . ?
C5 C4 C3 123.7(3) . . ?
C6 C5 C4 123.9(3) . . ?
C6 C5 C17 117.6(3) . . ?
C4 C5 C17 118.5(3) . . ?
N1 C6 C5 125.7(3) . . ?
N1 C6 C7 110.6(3) . . ?
C5 C6 C7 123.8(3) . . ?
C8 C7 C6 107.3(3) . . ?
C7 C8 C9 107.0(3) . . ?
N1 C9 C10 126.0(3) . . ?
N1 C9 C8 110.2(3) . . ?
C10 C9 C8 123.8(3) . . ?
C1 C10 C9 123.4(3) 3_775 . ?
C1 C10 C11 119.5(3) 3_775 . ?
C9 C10 C11 117.0(3) . . ?
C16 C11 C12 116.9(4) . . ?
C16 C11 C10 124.2(4) . . ?
C12 C11 C10 118.9(4) . . ?
N4 C12 C11 124.8(4) . . ?
C12 N4 C14 117.0(4) . . ?
N4 C14 C13 122.6(4) . . ?
N4 C14 C15 111.0(5) . . ?
C13 C14 C15 126.4(6) . . ?
O1 C15 C14 109.0(7) . . ?
C11 C16 C13 119.8(5) . . ?
C18 C17 C22 117.1(3) . . ?
C18 C17 C5 122.0(4) . . ?
C22 C17 C5 120.9(3) . . ?
C17 C18 C19 119.8(4) . . ?
C20 C19 C18 119.4(4) . . ?
N3 C20 C19 122.1(3) . . ?
N3 C20 C21 114.6(3) . . ?
C19 C20 C21 123.3(4) . . ?
O2 C21 C20 110.7(3) . . ?
N3 C22 C17 124.1(4) . . ?
C21 O2 Co1 127.9(3) . 2_745 ?

_refine_diff_density_max         0.710
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.088

