# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2235251'
loop_
_audit_author_name
_audit_author_address
'Liqun JIN'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 Cl2 Co N3'
_chemical_formula_weight         437.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -0.6628 2.9049 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.1324(3)
_cell_length_b                   11.1382(3)
_cell_length_c                   16.7579(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2077.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      53.10

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    6.145
_shelx_estimated_absorpt_T_min   0.404
_shelx_estimated_absorpt_T_max   0.440
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25981
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.146
_diffrn_reflns_theta_max         53.950
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3799
_reflns_number_gt                3378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.996

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.3962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.030(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3799
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3959(3) 0.8201(3) 0.7032(2) 0.0370(9) Uani 1 1 d . . . . .
H1 H 0.430169 0.865489 0.661006 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4320(3) 0.7020(3) 0.7150(2) 0.0326(8) Uani 1 1 d . . . . .
C3 C 0.3116(3) 0.8718(3) 0.7518(2) 0.0403(9) Uani 1 1 d . . . . .
H3 H 0.285509 0.951692 0.742191 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2644(3) 0.8066(4) 0.8152(3) 0.0464(10) Uani 1 1 d . . . . .
H4 H 0.205599 0.841996 0.848893 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3027(4) 0.6910(4) 0.8295(3) 0.0482(10) Uani 1 1 d . . . . .
H5 H 0.271286 0.647572 0.873562 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3870(3) 0.6376(3) 0.7797(3) 0.0417(9) Uani 1 1 d . . . . .
H6 H 0.413578 0.557951 0.789617 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5004(3) 0.5526(3) 0.6259(2) 0.0331(9) Uani 1 1 d . . . . .
C8 C 0.3939(3) 0.4717(4) 0.6315(3) 0.0464(10) Uani 1 1 d . . . . .
H8A H 0.323016 0.519402 0.647924 0.056 Uiso 1 1 calc R U . . .
H8B H 0.408749 0.410497 0.673113 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5967(3) 0.5146(3) 0.5694(2) 0.0318(8) Uani 1 1 d . . . . .
C10 C 0.3664(4) 0.4091(4) 0.5531(3) 0.0504(11) Uani 1 1 d . . . . .
H10A H 0.298262 0.353198 0.560884 0.060 Uiso 1 1 calc R U . . .
H10B H 0.341999 0.469645 0.512994 0.060 Uiso 1 1 calc R U . . .
C11 C 0.5840(4) 0.4172(4) 0.5186(2) 0.0409(9) Uani 1 1 d . . . . .
C12 C 0.4731(4) 0.3403(4) 0.5222(3) 0.0536(12) Uani 1 1 d . . . . .
H12A H 0.488389 0.270521 0.557362 0.064 Uiso 1 1 calc R U . . .
H12B H 0.454902 0.309418 0.468110 0.064 Uiso 1 1 calc R U . . .
C13 C 0.7801(4) 0.4677(4) 0.4671(2) 0.0489(11) Uani 1 1 d . . . . .
H13 H 0.844873 0.451742 0.431767 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7859(3) 0.5642(3) 0.5203(2) 0.0383(9) Uani 1 1 d . . . . .
C15 C 0.6792(4) 0.3960(4) 0.4665(2) 0.0485(11) Uani 1 1 d . . . . .
H15 H 0.674450 0.330943 0.429992 0.058 Uiso 1 1 calc R U . . .
C16 C 0.8855(3) 0.6553(4) 0.5238(2) 0.0420(10) Uani 1 1 d . . . . .
H16A H 0.961798 0.616968 0.507258 0.050 Uiso 1 1 calc R U . . .
H16B H 0.868081 0.721208 0.485936 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9583(3) 0.6162(4) 0.6589(3) 0.0477(11) Uani 1 1 d . . . . .
H17A H 0.911015 0.540980 0.656999 0.057 Uiso 1 1 calc R U . . .
H17B H 0.953895 0.647033 0.714261 0.057 Uiso 1 1 calc R U . . .
C18 C 1.0886(4) 0.5856(6) 0.6409(3) 0.0757(17) Uani 1 1 d . . . . .
H18A H 1.096003 0.560883 0.585020 0.114 Uiso 1 1 calc R U . . .
H18B H 1.114762 0.519839 0.675686 0.114 Uiso 1 1 calc R U . . .
H18C H 1.138948 0.656296 0.650474 0.114 Uiso 1 1 calc R U . . .
C19 C 0.9684(4) 0.8190(4) 0.5992(3) 0.0499(11) Uani 1 1 d . . . . .
H19A H 0.928101 0.872288 0.560217 0.060 Uiso 1 1 calc R U . . .
H19B H 1.049609 0.800876 0.578393 0.060 Uiso 1 1 calc R U . . .
C20 C 0.9807(5) 0.8850(5) 0.6774(3) 0.0673(14) Uani 1 1 d . . . . .
H20A H 0.900976 0.897012 0.700875 0.101 Uiso 1 1 calc R U . . .
H20B H 1.018689 0.963081 0.668063 0.101 Uiso 1 1 calc R U . . .
H20C H 1.030394 0.837664 0.714004 0.101 Uiso 1 1 calc R U . . .
Cl1 Cl 0.73356(8) 0.71492(9) 0.78075(5) 0.0436(2) Uani 1 1 d . . . . .
Cl2 Cl 0.66611(8) 0.89910(9) 0.58261(6) 0.0399(2) Uani 1 1 d . . . . .
Co1 Co 0.70569(4) 0.72455(5) 0.64705(3) 0.02990(14) Uani 1 1 d . . . . .
N1 N 0.5189(2) 0.6526(3) 0.66115(17) 0.0299(7) Uani 1 1 d . . . . .
N2 N 0.6952(3) 0.5843(3) 0.57000(17) 0.0324(6) Uani 1 1 d . . . . .
N3 N 0.8997(3) 0.7056(3) 0.60514(18) 0.0385(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.369(5) . ?
C1 C2 1.389(5) . ?
C1 H1 0.9500 . ?
C2 C6 1.393(5) . ?
C2 N1 1.432(4) . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.277(5) . ?
C7 C9 1.491(5) . ?
C7 C8 1.492(5) . ?
C8 C10 1.518(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.343(4) . ?
C9 C11 1.387(5) . ?
C10 C12 1.506(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.393(6) . ?
C11 C12 1.503(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.378(6) . ?
C13 C14 1.398(5) . ?
C13 H13 0.9500 . ?
C14 N2 1.328(4) . ?
C14 C16 1.505(5) . ?
C15 H15 0.9500 . ?
C16 N3 1.482(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.494(5) . ?
C17 C18 1.519(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N3 1.480(5) . ?
C19 C20 1.509(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Cl1 Co1 2.2644(10) . ?
Cl2 Co1 2.2673(11) . ?
Co1 N2 2.030(3) . ?
Co1 N1 2.241(3) . ?
Co1 N3 2.281(3) . ?

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
C3 C1 C2 120.8(4) . . ?
C3 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C6 119.5(4) . . ?
C1 C2 N1 118.0(3) . . ?
C6 C2 N1 122.4(3) . . ?
C1 C3 C4 119.6(4) . . ?
C1 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C2 119.3(4) . . ?
C5 C6 H6 120.3 . . ?
C2 C6 H6 120.3 . . ?
N1 C7 C9 115.2(3) . . ?
N1 C7 C8 128.7(3) . . ?
C9 C7 C8 116.1(3) . . ?
C7 C8 C10 112.6(4) . . ?
C7 C8 H8A 109.1 . . ?
C10 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C10 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C11 122.7(3) . . ?
N2 C9 C7 114.7(3) . . ?
C11 C9 C7 122.6(3) . . ?
C12 C10 C8 111.9(4) . . ?
C12 C10 H10A 109.2 . . ?
C8 C10 H10A 109.2 . . ?
C12 C10 H10B 109.2 . . ?
C8 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C9 C11 C15 116.1(4) . . ?
C9 C11 C12 120.4(4) . . ?
C15 C11 C12 123.5(4) . . ?
C11 C12 C10 111.8(3) . . ?
C11 C12 H12A 109.3 . . ?
C10 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C10 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C15 C13 C14 119.2(4) . . ?
C15 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N2 C14 C13 119.6(4) . . ?
N2 C14 C16 115.0(3) . . ?
C13 C14 C16 125.3(4) . . ?
C13 C15 C11 121.2(4) . . ?
C13 C15 H15 119.4 . . ?
C11 C15 H15 119.4 . . ?
N3 C16 C14 111.7(3) . . ?
N3 C16 H16A 109.3 . . ?
C14 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C14 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N3 C17 C18 116.5(4) . . ?
N3 C17 H17A 108.2 . . ?
C18 C17 H17A 108.2 . . ?
N3 C17 H17B 108.2 . . ?
C18 C17 H17B 108.2 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 113.8(4) . . ?
N3 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 Co1 N1 74.83(11) . . ?
N2 Co1 Cl1 126.94(9) . . ?
N1 Co1 Cl1 90.34(8) . . ?
N2 Co1 Cl2 110.22(9) . . ?
N1 Co1 Cl2 100.16(8) . . ?
Cl1 Co1 Cl2 122.58(4) . . ?
N2 Co1 N3 77.74(12) . . ?
N1 Co1 N3 151.42(11) . . ?
Cl1 Co1 N3 99.82(8) . . ?
Cl2 Co1 N3 96.69(9) . . ?
C7 N1 C2 121.1(3) . . ?
C7 N1 Co1 114.4(2) . . ?
C2 N1 Co1 123.8(2) . . ?
C14 N2 C9 121.2(3) . . ?
C14 N2 Co1 119.0(3) . . ?
C9 N2 Co1 119.8(2) . . ?
C19 N3 C16 108.4(3) . . ?
C19 N3 C17 112.6(3) . . ?
C16 N3 C17 110.4(3) . . ?
C19 N3 Co1 115.6(2) . . ?
C16 N3 Co1 102.6(2) . . ?
C17 N3 Co1 106.8(2) . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.042

