# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20201111_pink_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2053060'
loop_
_audit_author_name
_audit_author_address
'xusheng guo'
;Technical institute of Physics and Chemistry, CAS
China
;
_audit_update_record             
;
2020-12-29 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Cl2 Co N4'
_chemical_formula_sum            'C22 H20 Cl2 Co N4'
_chemical_formula_weight         470.25
_chemical_absolute_configuration rm
_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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.0415(16)
_cell_length_b                   8.9433(9)
_cell_length_c                   16.9729(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.314(4)
_cell_angle_gamma                90
_cell_volume                     2586.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      3.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0906 before and 0.0754 after correction.
The Ratio of minimum to maximum transmission is 0.8958.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18952
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         3.379
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5234
_reflns_number_total             5946
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 
;
 Flack x determined using 2107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.063(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5946
_refine_ls_number_restraints     310
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1474P)²+0.2724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.1968
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.702(4)
 0.298(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C8(H8), C14(H14),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.36553(7) 0.69207(12) 0.78498(8) 0.0361(3) Uani 1 1 d . U . . .
C1 C 0.3211(8) 0.6107(18) 1.0656(8) 0.063(3) Uani 1 1 d . U . . .
H1 H 0.3126 0.5884 1.1183 0.076 Uiso 1 1 calc R U . . .
N1 N 0.4315(5) 0.4847(9) 0.7776(7) 0.0462(19) Uani 1 1 d . U . . .
Cl1 Cl 0.48119(15) 0.8378(2) 0.7821(2) 0.0485(6) Uani 1 1 d . U . . .
Cl2 Cl 0.27309(16) 0.9012(3) 0.7880(2) 0.0523(6) Uani 1 1 d . U . . .
N2 N 0.3484(5) 0.6650(10) 0.9090(5) 0.046(2) Uani 1 1 d . U . . .
C2 C 0.5035(11) 0.212(2) 0.7538(13) 0.102(5) Uani 1 1 d . U . . .
H2 H 0.5274 0.1214 0.7426 0.123 Uiso 1 1 calc R U . . .
C4 C 0.5101(6) 0.4784(12) 0.7719(11) 0.070(4) Uani 1 1 d . U . . .
H4 H 0.5391 0.5658 0.7783 0.084 Uiso 1 1 calc R U . . .
N4 N 0.3379(5) 0.6679(9) 0.6617(5) 0.0403(18) Uani 1 1 d . U . . .
C3 C 0.2223(6) 0.5472(14) 0.7154(7) 0.051(2) Uani 1 1 d . U . . .
H3A H 0.1908 0.4591 0.7045 0.061 Uiso 1 1 calc R U . . .
H3B H 0.1869 0.6304 0.7240 0.061 Uiso 1 1 calc R U . . .
N3 N 0.2694(6) 0.5215(11) 0.7880(6) 0.0458(18) Uani 1 1 d . U . . .
C5 C 0.5493(9) 0.3456(17) 0.7569(11) 0.079(4) Uani 1 1 d . U . . .
H5 H 0.6033 0.3435 0.7491 0.095 Uiso 1 1 calc R U . . .
C6 C 0.3960(6) 0.7108(16) 0.9652(6) 0.050(2) Uani 1 1 d . U . . .
H6 H 0.4424 0.7580 0.9506 0.060 Uiso 1 1 calc R U . . .
C7 C 0.3809(7) 0.692(2) 1.0464(6) 0.060(3) Uani 1 1 d . U . . .
H7 H 0.4125 0.7372 1.0845 0.072 Uiso 1 1 calc R U . . .
C9 C 0.2690(7) 0.5551(14) 1.0079(7) 0.054(2) Uani 1 1 d . U . . .
H9 H 0.2251 0.5003 1.0228 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3780(6) 0.7146(13) 0.6007(6) 0.046(2) Uani 1 1 d . U . . .
H8 H 0.4218 0.7743 0.6094 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2835(6) 0.5826(13) 0.9290(7) 0.048(2) Uani 1 1 d . U . . .
C11 C 0.2272(7) 0.5508(17) 0.8626(8) 0.058(3) Uani 1 1 d . U . . .
H11A H 0.1954 0.4646 0.8759 0.070 Uiso 1 1 calc R U . . .
H11B H 0.1924 0.6357 0.8556 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3021(7) 0.3635(13) 0.7880(12) 0.062(3) Uani 1 1 d . U . . .
H12A H 0.2781 0.3079 0.7451 0.074 Uiso 1 1 calc R U . . .
H12B H 0.2876 0.3148 0.8369 0.074 Uiso 1 1 calc R U . . .
C13 C 0.3941(6) 0.3569(12) 0.7790(10) 0.056(3) Uani 1 1 d . U . . .
C14 C 0.4272(10) 0.218(2) 0.7670(13) 0.092(5) Uani 1 1 d . U . . .
H14 H 0.3969 0.1312 0.7682 0.110 Uiso 1 1 calc R U . . .
C15 C 0.2716(6) 0.5792(14) 0.6475(7) 0.049(2) Uani 1 1 d . U . . .
C16 C 0.2514(8) 0.5302(18) 0.5713(8) 0.062(3) Uani 1 1 d . U . . .
H16 H 0.2117 0.4599 0.5645 0.074 Uiso 1 1 calc R U . . .
C17 C 0.2904(7) 0.5864(15) 0.5061(7) 0.054(2) Uani 1 1 d . U . . .
C18 C 0.2785(10) 0.544(2) 0.4287(9) 0.078(4) Uani 1 1 d . U . . .
H18 H 0.2401 0.4732 0.4170 0.094 Uiso 1 1 calc R U . . .
C19 C 0.3236(9) 0.6052(19) 0.3668(8) 0.069(3) Uani 1 1 d . U . . .
H19 H 0.3122 0.5803 0.3147 0.083 Uiso 1 1 calc R U . . .
C20 C 0.3816(8) 0.697(3) 0.3828(7) 0.067(3) Uani 1 1 d . U . . .
H20 H 0.4101 0.7363 0.3409 0.081 Uiso 1 1 calc R U . . .
C21 C 0.4025(7) 0.7397(15) 0.4578(7) 0.055(3) Uani 1 1 d . U . . .
H21 H 0.4440 0.8054 0.4664 0.066 Uiso 1 1 calc R U . . .
C22 C 0.3579(7) 0.6787(14) 0.5235(5) 0.045(2) Uani 1 1 d . 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 2.173(9) . ?
Co1 Cl1 2.364(2) . ?
Co1 Cl2 2.446(3) . ?
Co1 N2 2.141(9) . ?
Co1 N4 2.153(9) . ?
Co1 N3 2.239(9) . ?
C1 H1 0.9300 . ?
C1 C7 1.30(2) . ?
C1 C9 1.41(2) . ?
N1 C4 1.346(13) . ?
N1 C13 1.309(13) . ?
N2 C6 1.314(15) . ?
N2 C10 1.373(13) . ?
C2 H2 0.9300 . ?
C2 C5 1.43(3) . ?
C2 C14 1.32(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(18) . ?
N4 C8 1.312(14) . ?
N4 C15 1.401(14) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 N3 1.485(15) . ?
C3 C15 1.458(15) . ?
N3 C11 1.484(16) . ?
N3 C12 1.519(15) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.413(14) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.386(17) . ?
C8 H8 0.9300 . ?
C8 C22 1.389(13) . ?
C10 C11 1.502(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.577(15) . ?
C13 C14 1.38(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.407(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(19) . ?
C17 C18 1.382(19) . ?
C17 C22 1.445(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.42(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.31(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(17) . ?
C21 H21 0.9300 . ?
C21 C22 1.460(15) . ?

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 Cl1 92.2(2) . . ?
N1 Co1 Cl2 170.9(2) . . ?
N1 Co1 N3 78.4(3) . . ?
Cl1 Co1 Cl2 96.67(11) . . ?
N2 Co1 N1 91.9(4) . . ?
N2 Co1 Cl1 101.6(3) . . ?
N2 Co1 Cl2 88.5(3) . . ?
N2 Co1 N4 156.1(3) . . ?
N2 Co1 N3 78.3(4) . . ?
N4 Co1 N1 88.2(4) . . ?
N4 Co1 Cl1 102.3(2) . . ?
N4 Co1 Cl2 87.7(2) . . ?
N4 Co1 N3 78.3(4) . . ?
N3 Co1 Cl1 170.5(3) . . ?
N3 Co1 Cl2 92.8(3) . . ?
C7 C1 H1 119.4 . . ?
C7 C1 C9 121.2(12) . . ?
C9 C1 H1 119.4 . . ?
C4 N1 Co1 123.7(6) . . ?
C13 N1 Co1 119.5(7) . . ?
C13 N1 C4 116.8(9) . . ?
C6 N2 Co1 126.2(7) . . ?
C6 N2 C10 119.0(10) . . ?
C10 N2 Co1 114.7(8) . . ?
C5 C2 H2 119.9 . . ?
C14 C2 H2 119.9 . . ?
C14 C2 C5 120.2(17) . . ?
N1 C4 H4 119.0 . . ?
N1 C4 C5 122.0(11) . . ?
C5 C4 H4 119.0 . . ?
C8 N4 Co1 128.6(7) . . ?
C8 N4 C15 117.9(9) . . ?
C15 N4 Co1 113.3(7) . . ?
H3A C3 H3B 107.9 . . ?
N3 C3 H3A 109.2 . . ?
N3 C3 H3B 109.2 . . ?
C15 C3 H3A 109.2 . . ?
C15 C3 H3B 109.2 . . ?
C15 C3 N3 112.0(9) . . ?
C3 N3 Co1 105.5(6) . . ?
C3 N3 C12 109.9(11) . . ?
C11 N3 Co1 104.9(7) . . ?
C11 N3 C3 114.7(9) . . ?
C11 N3 C12 110.1(11) . . ?
C12 N3 Co1 111.5(7) . . ?
C2 C5 H5 121.3 . . ?
C4 C5 C2 117.3(13) . . ?
C4 C5 H5 121.3 . . ?
N2 C6 H6 118.1 . . ?
N2 C6 C7 123.8(12) . . ?
C7 C6 H6 118.1 . . ?
C1 C7 C6 117.3(14) . . ?
C1 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C1 C9 H9 120.2 . . ?
C10 C9 C1 119.6(11) . . ?
C10 C9 H9 120.2 . . ?
N4 C8 H8 118.5 . . ?
N4 C8 C22 123.0(10) . . ?
C22 C8 H8 118.5 . . ?
N2 C10 C9 118.8(11) . . ?
N2 C10 C11 115.4(10) . . ?
C9 C10 C11 125.1(10) . . ?
N3 C11 C10 111.2(9) . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
N3 C12 C13 113.5(8) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
N1 C13 C12 117.0(9) . . ?
N1 C13 C14 125.8(12) . . ?
C14 C13 C12 117.0(11) . . ?
C2 C14 C13 117.4(16) . . ?
C2 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
N4 C15 C3 116.3(9) . . ?
N4 C15 C16 121.8(10) . . ?
C16 C15 C3 121.8(10) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(11) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C22 115.4(10) . . ?
C18 C17 C16 126.1(13) . . ?
C18 C17 C22 117.7(12) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(15) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(12) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 118.1 . . ?
C19 C20 C21 123.8(14) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.2(12) . . ?
C22 C21 H21 120.9 . . ?
C8 C22 C17 121.1(10) . . ?
C8 C22 C21 120.5(11) . . ?
C17 C22 C21 118.3(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N1 C4 C5 -171.3(13) . . . . ?
Co1 N1 C13 C12 -1(2) . . . . ?
Co1 N1 C13 C14 173.2(15) . . . . ?
Co1 N2 C6 C7 178.7(12) . . . . ?
Co1 N2 C10 C9 178.0(9) . . . . ?
Co1 N2 C10 C11 -11.4(13) . . . . ?
Co1 N4 C8 C22 173.2(8) . . . . ?
Co1 N4 C15 C3 13.6(13) . . . . ?
Co1 N4 C15 C16 -169.6(11) . . . . ?
Co1 N3 C11 C10 -42.0(12) . . . . ?
Co1 N3 C12 C13 -4.7(18) . . . . ?
C1 C9 C10 N2 -0.6(18) . . . . ?
C1 C9 C10 C11 -170.2(13) . . . . ?
N1 C4 C5 C2 -5(3) . . . . ?
N1 C13 C14 C2 1(3) . . . . ?
N2 C6 C7 C1 8(2) . . . . ?
N2 C10 C11 N3 37.7(15) . . . . ?
C4 N1 C13 C12 178.3(15) . . . . ?
C4 N1 C13 C14 -7(3) . . . . ?
N4 C8 C22 C17 0.0(18) . . . . ?
N4 C8 C22 C21 177.1(10) . . . . ?
N4 C15 C16 C17 -9(2) . . . . ?
C3 N3 C11 C10 -157.4(10) . . . . ?
C3 N3 C12 C13 112.0(15) . . . . ?
C3 C15 C16 C17 167.3(13) . . . . ?
N3 C3 C15 N4 -38.1(15) . . . . ?
N3 C3 C15 C16 145.0(13) . . . . ?
N3 C12 C13 N1 4(2) . . . . ?
N3 C12 C13 C14 -170.9(16) . . . . ?
C5 C2 C14 C13 4(3) . . . . ?
C6 N2 C10 C9 2.2(17) . . . . ?
C6 N2 C10 C11 172.8(11) . . . . ?
C7 C1 C9 C10 3(2) . . . . ?
C9 C1 C7 C6 -6(2) . . . . ?
C9 C10 C11 N3 -152.4(12) . . . . ?
C8 N4 C15 C3 -171.6(10) . . . . ?
C8 N4 C15 C16 5.2(17) . . . . ?
C10 N2 C6 C7 -6(2) . . . . ?
C11 N3 C12 C13 -120.7(14) . . . . ?
C12 N3 C11 C10 78.0(13) . . . . ?
C12 C13 C14 C2 175.4(19) . . . . ?
C13 N1 C4 C5 9(3) . . . . ?
C14 C2 C5 C4 -2(3) . . . . ?
C15 N4 C8 C22 -0.6(16) . . . . ?
C15 C3 N3 Co1 40.7(11) . . . . ?
C15 C3 N3 C11 155.7(11) . . . . ?
C15 C3 N3 C12 -79.6(12) . . . . ?
C15 C16 C17 C18 177.4(16) . . . . ?
C15 C16 C17 C22 8(2) . . . . ?
C16 C17 C18 C19 -177.9(16) . . . . ?
C16 C17 C22 C8 -3.8(18) . . . . ?
C16 C17 C22 C21 179.1(12) . . . . ?
C17 C18 C19 C20 4(3) . . . . ?
C18 C17 C22 C8 -173.9(14) . . . . ?
C18 C17 C22 C21 9.0(19) . . . . ?
C18 C19 C20 C21 0(3) . . . . ?
C19 C20 C21 C22 0(2) . . . . ?
C20 C21 C22 C8 178.2(13) . . . . ?
C20 C21 C22 C17 -4.7(18) . . . . ?
C22 C17 C18 C19 -9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.702(4)
2 0.298(4)

####################################################################### 
# 
# 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_20201110_pink_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2053061'
loop_
_audit_author_name
_audit_author_address
'xusheng guo'
; Technical Institute of Physics and Chemistry, CAS
China
;
_audit_update_record             
;
2020-12-29 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Cl2 Co N4'
_chemical_formula_sum            'C22 H20 Cl2 Co N4'
_chemical_formula_weight         470.25
_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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8073(13)
_cell_length_b                   12.9956(15)
_cell_length_c                   15.6175(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.956(5)
_cell_angle_gamma                90
_cell_volume                     2188.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4125
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0979 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.6976.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19479
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.842
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3186
_reflns_number_total             4943
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     291
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.065
_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)+(0.0386P)²+2.5934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1349
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.81014(5) 0.23249(4) 0.49902(3) 0.03702(17) Uani 1 1 d . U . . .
C1 C 0.6714(5) 0.3869(4) 0.6133(3) 0.0606(13) Uani 1 1 d . U . . .
H1 H 0.6476 0.3286 0.6425 0.073 Uiso 1 1 calc R U . . .
N1 N 0.7406(3) 0.3755(3) 0.5460(2) 0.0453(9) Uani 1 1 d . U . . .
Cl1 Cl 1.02117(11) 0.27961(10) 0.55077(7) 0.0556(3) Uani 1 1 d . U . . .
Cl2 Cl 0.76855(11) 0.12064(9) 0.61239(7) 0.0515(3) Uani 1 1 d . U . . .
C2 C 0.6344(6) 0.4814(5) 0.6406(4) 0.093(2) Uani 1 1 d . U . . .
H2 H 0.5870 0.4874 0.6878 0.111 Uiso 1 1 calc R U . . .
N2 N 0.8181(3) 0.3382(2) 0.3891(2) 0.0365(8) Uani 1 1 d . U . . .
N4 N 0.8807(3) 0.1328(3) 0.4059(2) 0.0409(8) Uani 1 1 d . U . . .
C4 C 0.7371(6) 0.5556(4) 0.5262(4) 0.0832(19) Uani 1 1 d . U . . .
H4 H 0.7596 0.6129 0.4951 0.100 Uiso 1 1 calc R U . . .
N3 N 0.6318(3) 0.2042(3) 0.4280(2) 0.0451(9) Uani 1 1 d . U . . .
C3 C 0.6687(7) 0.5665(5) 0.5969(5) 0.109(3) Uani 1 1 d . U . . .
H3 H 0.6459 0.6316 0.6148 0.131 Uiso 1 1 calc R U . . .
C8 C 0.9101(4) 0.1804(3) 0.3336(3) 0.0407(10) Uani 1 1 d . U . . .
C7 C 0.9180(4) 0.2963(3) 0.3386(3) 0.0429(10) Uani 1 1 d . U . . .
H7A H 0.9981 0.3162 0.3653 0.052 Uiso 1 1 calc R U . . .
H7B H 0.9105 0.3249 0.2811 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8497(4) 0.4399(3) 0.4274(3) 0.0432(10) Uani 1 1 d . U . . .
H6A H 0.8343 0.4935 0.3847 0.052 Uiso 1 1 calc R U . . .
H6B H 0.9370 0.4416 0.4467 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7713(4) 0.4584(3) 0.5025(3) 0.0460(11) Uani 1 1 d . U . . .
C9 C 0.9358(5) 0.1275(4) 0.2604(3) 0.0583(13) Uani 1 1 d . U . . .
H9 H 0.9521 0.1622 0.2103 0.070 Uiso 1 1 calc R U . . .
C10 C 0.9365(6) 0.0219(4) 0.2638(4) 0.0762(17) Uani 1 1 d . U . . .
H10 H 0.9541 -0.0158 0.2155 0.091 Uiso 1 1 calc R U . . .
C11 C 0.9116(5) -0.0280(4) 0.3372(4) 0.0690(15) Uani 1 1 d . U . . .
H11 H 0.9139 -0.0994 0.3401 0.083 Uiso 1 1 calc R U . . .
C12 C 0.8832(4) 0.0294(3) 0.4068(3) 0.0532(12) Uani 1 1 d . U . . .
H12 H 0.8648 -0.0046 0.4567 0.064 Uiso 1 1 calc R U . . .
C13 C 0.6984(4) 0.3417(3) 0.3374(3) 0.0443(10) Uani 1 1 d . U . . .
H13A H 0.7145 0.3379 0.2772 0.053 Uiso 1 1 calc R U . . .
H13B H 0.6592 0.4075 0.3469 0.053 Uiso 1 1 calc R U . . .
C14 C 0.6092(4) 0.2572(3) 0.3569(3) 0.0398(9) Uani 1 1 d . U . . .
C15 C 0.5006(4) 0.2396(3) 0.3004(3) 0.0456(10) Uani 1 1 d . U . . .
C16 C 0.4745(5) 0.2971(4) 0.2242(3) 0.0572(12) Uani 1 1 d . U . . .
H16 H 0.5301 0.3463 0.2070 0.069 Uiso 1 1 calc R U . . .
C17 C 0.3644(5) 0.2784(5) 0.1759(4) 0.0746(15) Uani 1 1 d . U . . .
H17 H 0.3460 0.3153 0.1256 0.090 Uiso 1 1 calc R U . . .
C18 C 0.2811(6) 0.2049(5) 0.2018(4) 0.0855(18) Uani 1 1 d . U . . .
H18 H 0.2070 0.1945 0.1690 0.103 Uiso 1 1 calc R U . . .
C19 C 0.3054(5) 0.1491(5) 0.2727(4) 0.0832(18) Uani 1 1 d . U . . .
H19 H 0.2488 0.0997 0.2881 0.100 Uiso 1 1 calc R U . . .
C20 C 0.4160(5) 0.1644(4) 0.3245(4) 0.0592(13) Uani 1 1 d . U . . .
C21 C 0.4438(5) 0.1103(4) 0.4013(4) 0.0799(18) Uani 1 1 d . U . . .
H21 H 0.3902 0.0597 0.4187 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5484(5) 0.1321(4) 0.4494(4) 0.0711(16) Uani 1 1 d . U . . .
H22 H 0.5647 0.0957 0.5002 0.085 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
Co1 N1 2.152(4) . ?
Co1 Cl1 2.4445(13) . ?
Co1 Cl2 2.3579(11) . ?
Co1 N2 2.206(3) . ?
Co1 N4 2.128(3) . ?
Co1 N3 2.188(4) . ?
C1 H1 0.9300 . ?
C1 N1 1.340(5) . ?
C1 C2 1.368(7) . ?
N1 C5 1.327(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(8) . ?
N2 C7 1.484(5) . ?
N2 C6 1.481(5) . ?
N2 C13 1.477(5) . ?
N4 C8 1.344(5) . ?
N4 C12 1.344(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.378(8) . ?
C4 C5 1.375(6) . ?
N3 C14 1.315(5) . ?
N3 C22 1.357(5) . ?
C3 H3 0.9300 . ?
C8 C7 1.510(6) . ?
C8 C9 1.379(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.513(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.360(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(7) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.507(6) . ?
C14 C15 1.437(6) . ?
C15 C16 1.416(6) . ?
C15 C20 1.407(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.334(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.411(7) . ?
C20 C21 1.405(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.344(7) . ?
C22 H22 0.9300 . ?

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 Cl1 90.61(10) . . ?
N1 Co1 Cl2 100.81(10) . . ?
N1 Co1 N2 76.14(13) . . ?
N1 Co1 N3 90.11(14) . . ?
Cl2 Co1 Cl1 97.35(4) . . ?
N2 Co1 Cl1 90.91(9) . . ?
N2 Co1 Cl2 171.25(10) . . ?
N4 Co1 N1 155.30(13) . . ?
N4 Co1 Cl1 90.48(10) . . ?
N4 Co1 Cl2 103.52(10) . . ?
N4 Co1 N2 79.16(12) . . ?
N4 Co1 N3 84.02(13) . . ?
N3 Co1 Cl1 168.26(10) . . ?
N3 Co1 Cl2 94.02(10) . . ?
N3 Co1 N2 77.89(12) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.3(5) . . ?
C2 C1 H1 118.8 . . ?
C1 N1 Co1 126.1(3) . . ?
C5 N1 Co1 114.9(3) . . ?
C5 N1 C1 118.9(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(5) . . ?
C3 C2 H2 120.8 . . ?
C7 N2 Co1 104.7(2) . . ?
C6 N2 Co1 105.2(2) . . ?
C6 N2 C7 112.7(3) . . ?
C13 N2 Co1 111.4(2) . . ?
C13 N2 C7 111.3(3) . . ?
C13 N2 C6 111.2(3) . . ?
C8 N4 Co1 114.2(3) . . ?
C12 N4 Co1 127.5(3) . . ?
C12 N4 C8 117.6(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C5 C4 C3 118.6(5) . . ?
C14 N3 Co1 116.5(3) . . ?
C14 N3 C22 118.8(4) . . ?
C22 N3 Co1 124.6(3) . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N4 C8 C7 115.6(4) . . ?
N4 C8 C9 122.7(4) . . ?
C9 C8 C7 121.7(4) . . ?
N2 C7 C8 110.7(3) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N2 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
N2 C6 C5 109.2(3) . . ?
H6A C6 H6B 108.3 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
N1 C5 C4 121.8(4) . . ?
N1 C5 C6 116.1(4) . . ?
C4 C5 C6 122.0(4) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.8(5) . . ?
C10 C9 H9 121.1 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(5) . . ?
C12 C11 H11 120.7 . . ?
N4 C12 C11 122.8(5) . . ?
N4 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
N2 C13 H13A 108.6 . . ?
N2 C13 H13B 108.6 . . ?
N2 C13 C14 114.6(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
N3 C14 C13 117.9(4) . . ?
N3 C14 C15 122.1(4) . . ?
C15 C14 C13 119.9(4) . . ?
C16 C15 C14 122.6(4) . . ?
C20 C15 C14 117.7(4) . . ?
C20 C15 C16 119.7(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.6(5) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.7(5) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.3(6) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(6) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.0(5) . . ?
C21 C20 C15 118.1(4) . . ?
C21 C20 C19 122.8(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(5) . . ?
C22 C21 H21 120.2 . . ?
N3 C22 H22 118.1 . . ?
C21 C22 N3 123.7(5) . . ?
C21 C22 H22 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N1 C5 C4 -178.0(4) . . . . ?
Co1 N1 C5 C6 0.0(5) . . . . ?
Co1 N2 C7 C8 41.7(4) . . . . ?
Co1 N2 C6 C5 -45.0(4) . . . . ?
Co1 N2 C13 C14 -13.6(4) . . . . ?
Co1 N4 C8 C7 14.1(5) . . . . ?
Co1 N4 C8 C9 -168.1(4) . . . . ?
Co1 N4 C12 C11 168.9(4) . . . . ?
Co1 N3 C14 C13 -8.2(5) . . . . ?
Co1 N3 C14 C15 174.5(3) . . . . ?
Co1 N3 C22 C21 -174.6(5) . . . . ?
C1 N1 C5 C4 1.9(7) . . . . ?
C1 N1 C5 C6 179.9(4) . . . . ?
C1 C2 C3 C4 1.1(12) . . . . ?
N1 C1 C2 C3 0.6(10) . . . . ?
C2 C1 N1 Co1 177.8(5) . . . . ?
C2 C1 N1 C5 -2.1(8) . . . . ?
N2 C6 C5 N1 31.7(5) . . . . ?
N2 C6 C5 C4 -150.3(5) . . . . ?
N2 C13 C14 N3 14.9(5) . . . . ?
N2 C13 C14 C15 -167.7(4) . . . . ?
N4 C8 C7 N2 -39.4(5) . . . . ?
N4 C8 C9 C10 -3.0(7) . . . . ?
N3 C14 C15 C16 179.2(4) . . . . ?
N3 C14 C15 C20 1.5(6) . . . . ?
C3 C4 C5 N1 -0.2(9) . . . . ?
C3 C4 C5 C6 -178.1(6) . . . . ?
C8 N4 C12 C11 -1.4(7) . . . . ?
C8 C9 C10 C11 0.5(9) . . . . ?
C7 N2 C6 C5 -158.4(3) . . . . ?
C7 N2 C13 C14 102.8(4) . . . . ?
C7 C8 C9 C10 174.6(5) . . . . ?
C6 N2 C7 C8 155.4(3) . . . . ?
C6 N2 C13 C14 -130.6(4) . . . . ?
C5 C4 C3 C2 -1.3(12) . . . . ?
C9 C8 C7 N2 142.8(4) . . . . ?
C9 C10 C11 C12 1.5(9) . . . . ?
C10 C11 C12 N4 -1.1(8) . . . . ?
C12 N4 C8 C7 -174.3(4) . . . . ?
C12 N4 C8 C9 3.5(6) . . . . ?
C13 N2 C7 C8 -78.8(4) . . . . ?
C13 N2 C6 C5 75.7(4) . . . . ?
C13 C14 C15 C16 1.9(6) . . . . ?
C13 C14 C15 C20 -175.8(4) . . . . ?
C14 N3 C22 C21 0.9(8) . . . . ?
C14 C15 C16 C17 -176.7(4) . . . . ?
C14 C15 C20 C19 176.7(5) . . . . ?
C14 C15 C20 C21 -1.0(7) . . . . ?
C15 C16 C17 C18 0.2(8) . . . . ?
C15 C20 C21 C22 0.6(9) . . . . ?
C16 C15 C20 C19 -1.0(7) . . . . ?
C16 C15 C20 C21 -178.8(5) . . . . ?
C16 C17 C18 C19 -1.2(10) . . . . ?
C17 C18 C19 C20 1.1(10) . . . . ?
C18 C19 C20 C15 0.1(9) . . . . ?
C18 C19 C20 C21 177.7(6) . . . . ?
C19 C20 C21 C22 -177.0(6) . . . . ?
C20 C15 C16 C17 0.9(7) . . . . ?
C20 C21 C22 N3 -0.5(10) . . . . ?
C22 N3 C14 C13 175.9(4) . . . . ?
C22 N3 C14 C15 -1.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
