# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Co-1NO2
_audit_block_doi                 10.5517/ccdc.csd.cc2hpkxp
_database_code_depnum_ccdc_archive 'CCDC 2314643'
loop_
_audit_author_name
_audit_author_address
'Kuntal Pal'
;University of Calcutta
India
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-12-15
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Co N6 O5, 1[CH2Cl2]'
_chemical_formula_sum            'C23 H19 Cl2 Co N6 O5'
_chemical_formula_weight         589.27
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.2770(5)
_cell_length_b                   11.8990(6)
_cell_length_c                   12.2515(6)
_cell_angle_alpha                63.338(2)
_cell_angle_beta                 81.714(2)
_cell_angle_gamma                70.818(2)
_cell_volume                     1264.54(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      4.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.674
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1341 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.4652.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21742
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.700
_diffrn_reflns_theta_max         66.700
_diffrn_reflns_theta_min         4.555
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4139
_reflns_number_total             4392
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.064
_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)+(0.0515P)²+1.5659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15), C2(H2), C5(H5), C14(H14), C3(H3), C13(H13), C12(H12),
 C17(H17)
1.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_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 0.77802(4) 0.54106(4) 0.25302(3) 0.01498(14) Uani 1 1 d . . . . .
O2 O 0.95418(19) 0.56029(17) 0.19460(16) 0.0186(4) Uani 1 1 d . . . . .
O1 O 0.73398(18) 0.70561(17) 0.25976(16) 0.0182(4) Uani 1 1 d . . . . .
O3 O 0.69385(19) 0.62614(18) 0.09758(16) 0.0218(4) Uani 1 1 d . . . . .
N1 N 0.6038(2) 0.5145(2) 0.30918(19) 0.0167(5) Uani 1 1 d . . . . .
N3 N 0.8588(2) 0.4406(2) 0.41456(19) 0.0161(5) Uani 1 1 d . . . . .
O5 O 0.2555(2) 1.0809(2) 0.4157(2) 0.0338(5) Uani 1 1 d . . . . .
N2 N 0.8315(2) 0.3728(2) 0.25423(19) 0.0179(5) Uani 1 1 d . . . . .
O4 O 0.1536(2) 0.9371(2) 0.4426(2) 0.0344(5) Uani 1 1 d . . . . .
N6 N 0.2560(3) 0.9768(2) 0.4156(2) 0.0249(5) Uani 1 1 d . . . . .
N5 N 0.3634(3) 0.3539(3) 0.3370(2) 0.0312(6) Uani 1 1 d . . . . .
C7 C 0.4986(3) 0.5965(3) 0.3339(2) 0.0182(5) Uani 1 1 d . . . . .
H7 H 0.413445 0.576670 0.351568 0.022 Uiso 1 1 calc R U . . .
C11 C 0.9474(3) 0.3214(3) 0.4335(2) 0.0168(5) Uani 1 1 d . . . . .
C15 C 0.8345(3) 0.4812(3) 0.5040(2) 0.0173(5) Uani 1 1 d . . . . .
H15 H 0.770785 0.565068 0.489906 0.021 Uiso 1 1 calc R U . . .
C9 C 0.7219(3) 0.3245(3) 0.2843(2) 0.0196(6) Uani 1 1 d . . . . .
C1 C 0.6207(3) 0.7616(3) 0.3013(2) 0.0173(5) Uani 1 1 d . . . . .
C6 C 0.5023(3) 0.7146(3) 0.3362(2) 0.0173(5) Uani 1 1 d . . . . .
C8 C 0.5971(3) 0.4002(3) 0.3051(2) 0.0198(6) Uani 1 1 d . . . . .
C22 C 0.4695(3) 0.3710(3) 0.3219(3) 0.0221(6) Uani 1 1 d . . . . .
C2 C 0.6139(3) 0.8767(3) 0.3131(2) 0.0197(6) Uani 1 1 d . . . . .
H2 H 0.692554 0.907356 0.293032 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3817(3) 0.9007(3) 0.3800(2) 0.0198(6) Uani 1 1 d . . . . .
C18 C 0.7542(3) 0.6774(3) -0.0027(2) 0.0229(6) Uani 1 1 d . . . . .
C5 C 0.3820(3) 0.7883(3) 0.3736(2) 0.0193(6) Uani 1 1 d . . . . .
H5 H 0.301622 0.760188 0.394302 0.023 Uiso 1 1 calc R U . . .
C16 C 0.9829(3) 0.6175(3) 0.0818(2) 0.0222(6) Uani 1 1 d . . . . .
C14 C 0.8999(3) 0.4041(3) 0.6151(2) 0.0200(6) Uani 1 1 d . . . . .
H14 H 0.881362 0.433769 0.677590 0.024 Uiso 1 1 calc R U . . .
C10 C 0.9588(3) 0.2881(3) 0.3262(2) 0.0197(6) Uani 1 1 d . . . . .
H10A H 1.040699 0.306212 0.276333 0.024 Uiso 1 1 calc R U . . .
H10B H 0.966893 0.193879 0.354850 0.024 Uiso 1 1 calc R U . . .
N4 N 0.7568(3) 0.0986(3) 0.2851(3) 0.0385(7) Uani 1 1 d . . . . .
C3 C 0.4981(3) 0.9442(3) 0.3522(2) 0.0221(6) Uani 1 1 d . . . . .
H3 H 0.496369 1.020336 0.360450 0.027 Uiso 1 1 calc R U . . .
C13 C 0.9937(3) 0.2818(3) 0.6348(2) 0.0223(6) Uani 1 1 d . . . . .
H13 H 1.041101 0.227690 0.710602 0.027 Uiso 1 1 calc R U . . .
C12 C 1.0178(3) 0.2394(3) 0.5433(2) 0.0216(6) Uani 1 1 d . . . . .
H12 H 1.081198 0.155930 0.555544 0.026 Uiso 1 1 calc R U . . .
C17 C 0.8904(3) 0.6763(3) -0.0142(3) 0.0295(7) Uani 1 1 d . . . . .
H17 H 0.923152 0.719259 -0.094163 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7386(3) 0.1972(3) 0.2877(3) 0.0238(6) Uani 1 1 d . . . . .
C20 C 1.1293(3) 0.6213(3) 0.0567(3) 0.0324(7) Uani 1 1 d . . . . .
H20A H 1.137740 0.698259 0.062324 0.049 Uiso 1 1 calc R U . . .
H20B H 1.155140 0.627293 -0.025431 0.049 Uiso 1 1 calc R U . . .
H20C H 1.190468 0.540883 0.116999 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6621(4) 0.7456(3) -0.1136(3) 0.0357(8) Uani 1 1 d . . . . .
H19A H 0.594986 0.698567 -0.101236 0.054 Uiso 1 1 calc R U . . .
H19B H 0.718165 0.746203 -0.185623 0.054 Uiso 1 1 calc R U . . .
H19C H 0.613454 0.836475 -0.126091 0.054 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 O2 1.8957(18) . ?
Co1 O1 1.8967(18) . ?
Co1 O3 1.8892(18) . ?
Co1 N1 1.897(2) . ?
Co1 N3 1.932(2) . ?
Co1 N2 1.888(2) . ?
O2 C16 1.276(3) . ?
O1 C1 1.297(3) . ?
O3 C18 1.274(3) . ?
N1 C7 1.300(4) . ?
N1 C8 1.407(3) . ?
N3 C11 1.346(3) . ?
N3 C15 1.348(3) . ?
O5 N6 1.237(3) . ?
N2 C9 1.360(3) . ?
N2 C10 1.475(3) . ?
O4 N6 1.236(3) . ?
N6 C4 1.450(4) . ?
N5 C22 1.148(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.432(4) . ?
C11 C10 1.514(4) . ?
C11 C12 1.388(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.372(4) . ?
C9 C8 1.370(4) . ?
C9 C21 1.448(4) . ?
C1 C6 1.434(4) . ?
C1 C2 1.418(4) . ?
C6 C5 1.412(4) . ?
C8 C22 1.428(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.358(4) . ?
C4 C5 1.374(4) . ?
C4 C3 1.396(4) . ?
C18 C17 1.383(4) . ?
C18 C19 1.509(4) . ?
C5 H5 0.9500 . ?
C16 C17 1.387(4) . ?
C16 C20 1.503(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.391(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N4 C21 1.141(4) . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C17 H17 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
O2 Co1 O1 87.64(8) . . ?
O2 Co1 N1 177.03(8) . . ?
O2 Co1 N3 87.16(8) . . ?
O1 Co1 N1 95.27(9) . . ?
O1 Co1 N3 94.18(8) . . ?
O3 Co1 O2 95.81(8) . . ?
O3 Co1 O1 90.20(8) . . ?
O3 Co1 N1 83.58(9) . . ?
O3 Co1 N3 174.82(8) . . ?
N1 Co1 N3 93.24(9) . . ?
N2 Co1 O2 90.52(9) . . ?
N2 Co1 O1 176.08(9) . . ?
N2 Co1 O3 93.43(9) . . ?
N2 Co1 N1 86.61(9) . . ?
N2 Co1 N3 82.28(9) . . ?
C16 O2 Co1 124.03(18) . . ?
C1 O1 Co1 126.13(16) . . ?
C18 O3 Co1 124.32(18) . . ?
C7 N1 Co1 125.93(18) . . ?
C7 N1 C8 123.4(2) . . ?
C8 N1 Co1 110.16(18) . . ?
C11 N3 Co1 114.29(17) . . ?
C11 N3 C15 120.1(2) . . ?
C15 N3 Co1 125.58(19) . . ?
C9 N2 Co1 109.75(18) . . ?
C9 N2 C10 117.0(2) . . ?
C10 N2 Co1 110.64(16) . . ?
O5 N6 C4 118.1(2) . . ?
O4 N6 O5 122.6(2) . . ?
O4 N6 C4 119.3(2) . . ?
N1 C7 H7 117.8 . . ?
N1 C7 C6 124.4(2) . . ?
C6 C7 H7 117.8 . . ?
N3 C11 C10 113.7(2) . . ?
N3 C11 C12 121.2(2) . . ?
C12 C11 C10 125.1(2) . . ?
N3 C15 H15 119.3 . . ?
N3 C15 C14 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
N2 C9 C8 119.0(2) . . ?
N2 C9 C21 119.3(3) . . ?
C8 C9 C21 121.7(3) . . ?
O1 C1 C6 124.3(2) . . ?
O1 C1 C2 117.7(2) . . ?
C2 C1 C6 118.1(2) . . ?
C7 C6 C1 123.4(2) . . ?
C5 C6 C7 117.5(2) . . ?
C5 C6 C1 119.1(2) . . ?
N1 C8 C22 121.1(2) . . ?
C9 C8 N1 113.4(2) . . ?
C9 C8 C22 125.5(2) . . ?
N5 C22 C8 175.8(3) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C5 C4 N6 118.8(2) . . ?
C5 C4 C3 122.0(3) . . ?
C3 C4 N6 119.2(2) . . ?
O3 C18 C17 125.4(3) . . ?
O3 C18 C19 114.0(3) . . ?
C17 C18 C19 120.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
O2 C16 C17 125.3(3) . . ?
O2 C16 C20 114.8(2) . . ?
C17 C16 C20 119.9(3) . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 118.9(2) . . ?
C13 C14 H14 120.5 . . ?
N2 C10 C11 105.8(2) . . ?
N2 C10 H10A 110.6 . . ?
N2 C10 H10B 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.1 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C18 C17 C16 125.1(3) . . ?
C18 C17 H17 117.5 . . ?
C16 C17 H17 117.5 . . ?
N4 C21 C9 176.1(3) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 O2 C16 C17 1.5(4) . . . . ?
Co1 O2 C16 C20 179.94(19) . . . . ?
Co1 O1 C1 C6 -7.8(4) . . . . ?
Co1 O1 C1 C2 172.18(17) . . . . ?
Co1 O3 C18 C17 1.6(4) . . . . ?
Co1 O3 C18 C19 -176.93(19) . . . . ?
Co1 N1 C7 C6 -7.7(4) . . . . ?
Co1 N1 C8 C9 11.2(3) . . . . ?
Co1 N1 C8 C22 -168.8(2) . . . . ?
Co1 N3 C11 C10 -3.3(3) . . . . ?
Co1 N3 C11 C12 177.55(19) . . . . ?
Co1 N3 C15 C14 -178.13(18) . . . . ?
Co1 N2 C9 C8 1.4(3) . . . . ?
Co1 N2 C9 C21 178.44(19) . . . . ?
Co1 N2 C10 C11 37.6(2) . . . . ?
O2 Co1 O1 C1 -175.9(2) . . . . ?
O2 Co1 O3 C18 -2.1(2) . . . . ?
O2 Co1 N2 C9 -175.03(17) . . . . ?
O2 Co1 N2 C10 54.33(17) . . . . ?
O2 C16 C17 C18 -2.7(5) . . . . ?
O1 Co1 O2 C16 -89.3(2) . . . . ?
O1 Co1 O3 C18 85.5(2) . . . . ?
O1 Co1 N1 C7 2.9(2) . . . . ?
O1 Co1 N1 C8 174.89(16) . . . . ?
O1 C1 C6 C7 2.9(4) . . . . ?
O1 C1 C6 C5 -176.4(2) . . . . ?
O1 C1 C2 C3 177.9(2) . . . . ?
O3 Co1 O2 C16 0.6(2) . . . . ?
O3 Co1 O1 C1 88.3(2) . . . . ?
O3 Co1 N1 C7 -86.8(2) . . . . ?
O3 Co1 N1 C8 85.29(17) . . . . ?
O3 Co1 N2 C9 -79.18(17) . . . . ?
O3 Co1 N2 C10 150.18(17) . . . . ?
O3 C18 C17 C16 1.0(5) . . . . ?
N1 Co1 O1 C1 4.8(2) . . . . ?
N1 Co1 O3 C18 -179.2(2) . . . . ?
N1 Co1 N2 C9 4.17(17) . . . . ?
N1 Co1 N2 C10 -126.47(17) . . . . ?
N1 C7 C6 C1 5.4(4) . . . . ?
N1 C7 C6 C5 -175.3(2) . . . . ?
N3 Co1 O2 C16 176.4(2) . . . . ?
N3 Co1 O1 C1 -88.9(2) . . . . ?
N3 Co1 N1 C7 97.4(2) . . . . ?
N3 Co1 N1 C8 -90.61(17) . . . . ?
N3 Co1 N2 C9 97.91(17) . . . . ?
N3 Co1 N2 C10 -32.73(17) . . . . ?
N3 C11 C10 N2 -21.6(3) . . . . ?
N3 C11 C12 C13 0.9(4) . . . . ?
N3 C15 C14 C13 0.4(4) . . . . ?
O5 N6 C4 C5 -176.9(2) . . . . ?
O5 N6 C4 C3 2.5(4) . . . . ?
N2 Co1 O2 C16 94.1(2) . . . . ?
N2 Co1 O3 C18 -93.0(2) . . . . ?
N2 Co1 N1 C7 179.4(2) . . . . ?
N2 Co1 N1 C8 -8.55(17) . . . . ?
N2 C9 C8 N1 -8.6(3) . . . . ?
N2 C9 C8 C22 171.5(2) . . . . ?
O4 N6 C4 C5 2.1(4) . . . . ?
O4 N6 C4 C3 -178.6(2) . . . . ?
N6 C4 C5 C6 178.4(2) . . . . ?
N6 C4 C3 C2 -176.8(2) . . . . ?
C7 N1 C8 C9 -176.5(2) . . . . ?
C7 N1 C8 C22 3.5(4) . . . . ?
C7 C6 C5 C4 178.5(2) . . . . ?
C11 N3 C15 C14 0.9(4) . . . . ?
C15 N3 C11 C10 177.6(2) . . . . ?
C15 N3 C11 C12 -1.6(4) . . . . ?
C15 C14 C13 C12 -1.0(4) . . . . ?
C9 N2 C10 C11 -89.1(3) . . . . ?
C1 C6 C5 C4 -2.2(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C6 C1 C2 C3 -2.1(4) . . . . ?
C8 N1 C7 C6 -178.7(2) . . . . ?
C2 C1 C6 C7 -177.1(2) . . . . ?
C2 C1 C6 C5 3.6(4) . . . . ?
C5 C4 C3 C2 2.5(4) . . . . ?
C14 C13 C12 C11 0.4(4) . . . . ?
C10 N2 C9 C8 128.5(3) . . . . ?
C10 N2 C9 C21 -54.4(3) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C12 C11 C10 N2 157.5(2) . . . . ?
C21 C9 C8 N1 174.4(2) . . . . ?
C21 C9 C8 C22 -5.5(4) . . . . ?
C20 C16 C17 C18 178.9(3) . . . . ?
C19 C18 C17 C16 179.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.835 -0.362 0.000 285.6 69.5 '2 DCM'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_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_Co-1H
_audit_block_doi                 10.5517/ccdc.csd.cc2hpkzr
_database_code_depnum_ccdc_archive 'CCDC 2314645'
loop_
_audit_author_name
_audit_author_address
'Kuntal Pal'
;University of Calcutta
India
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Co N5 O3, 1[CH2Cl2]'
_chemical_formula_sum            'C22 H18 Co N5 O3'
_chemical_formula_weight         459.34
_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                   8.8732(16)
_cell_length_b                   10.2837(19)
_cell_length_c                   14.993(3)
_cell_angle_alpha                78.404(4)
_cell_angle_beta                 79.175(4)
_cell_angle_gamma                66.066(4)
_cell_volume                     1216.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.88
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1266 before and 0.0720 after correction. The Ratio of minimum to maximum transmission is 0.6196. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29507
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.252
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'three-circle diffractometer'
_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_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4619
_reflns_number_total             5220
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.073
_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)+(0.0705P)²+0.5385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C12(H12), C15(H15), C5(H5), C14(H14), C13(H13), C4(H4),
 C3(H3), C17(H17)
1.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_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 0.63203(3) 0.47860(3) 0.75807(2) 0.03250(10) Uani 1 1 d . . . . .
N1 N 0.59035(19) 0.65606(17) 0.68152(10) 0.0305(3) Uani 1 1 d . . . . .
O1 O 0.40507(18) 0.51022(16) 0.79326(10) 0.0392(3) Uani 1 1 d . . . . .
N2 N 0.8603(2) 0.43633(19) 0.71582(12) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.6817(2) 0.30001(17) 0.83409(11) 0.0449(4) Uani 1 1 d . . . . .
N3 N 0.6523(2) 0.37457(18) 0.66031(11) 0.0331(3) Uani 1 1 d . . . . .
O3 O 0.6331(2) 0.58067(18) 0.84893(10) 0.0450(4) Uani 1 1 d . . . . .
C6 C 0.2952(3) 0.7549(2) 0.72247(14) 0.0393(4) Uani 1 1 d . . . . .
C8 C 0.7388(3) 0.6655(2) 0.63548(14) 0.0362(4) Uani 1 1 d . . . . .
C10 C 0.9351(3) 0.2935(2) 0.68618(16) 0.0403(5) Uani 1 1 d . . . . .
H10A H 0.961660 0.219071 0.738624 0.048 Uiso 1 1 calc R U . . .
H10B H 1.036176 0.283534 0.644864 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8078(2) 0.2821(2) 0.63809(14) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.8762(2) 0.5432(2) 0.65141(14) 0.0363(4) Uani 1 1 d . . . . .
C1 C 0.2798(3) 0.6286(2) 0.77338(13) 0.0366(4) Uani 1 1 d . . . . .
C7 C 0.4482(3) 0.7618(2) 0.67909(14) 0.0364(4) Uani 1 1 d . . . . .
H7 H 0.446166 0.849319 0.646262 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1188(3) 0.6306(3) 0.80310(16) 0.0491(6) Uani 1 1 d . . . . .
H2 H 0.106044 0.547082 0.834009 0.059 Uiso 1 1 calc R U . . .
C21 C 1.0345(3) 0.5282(3) 0.59951(16) 0.0429(5) Uani 1 1 d . . . . .
C12 C 0.8413(3) 0.1924(2) 0.57459(16) 0.0455(5) Uani 1 1 d . . . . .
H12 H 0.948950 0.127833 0.560286 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5292(3) 0.3829(2) 0.61793(15) 0.0413(5) Uani 1 1 d . . . . .
H15 H 0.422484 0.448915 0.632437 0.050 Uiso 1 1 calc R U . . .
N4 N 1.1601(3) 0.5116(3) 0.55789(17) 0.0576(6) Uani 1 1 d . . . . .
N5 N 0.7404(3) 0.8788(3) 0.5149(2) 0.0716(7) Uani 1 1 d . . . . .
C5 C 0.1499(3) 0.8792(3) 0.70951(19) 0.0572(7) Uani 1 1 d . . . . .
H5 H 0.159604 0.963826 0.678348 0.069 Uiso 1 1 calc R U . . .
C14 C 0.5561(3) 0.2968(3) 0.55375(18) 0.0519(6) Uani 1 1 d . . . . .
H14 H 0.468639 0.304006 0.524687 0.062 Uiso 1 1 calc R U . . .
C22 C 0.7415(3) 0.7855(3) 0.57088(17) 0.0455(5) Uani 1 1 d . . . . .
C18 C 0.6854(3) 0.5211(3) 0.92529(15) 0.0499(6) Uani 1 1 d . . . . .
C13 C 0.7131(4) 0.1993(3) 0.53228(18) 0.0539(6) Uani 1 1 d . . . . .
H13 H 0.732741 0.138341 0.489512 0.065 Uiso 1 1 calc R U . . .
C16 C 0.7269(3) 0.2762(3) 0.91281(16) 0.0518(6) Uani 1 1 d . . . . .
C4 C -0.0039(3) 0.8789(3) 0.7413(2) 0.0707(9) Uani 1 1 d . . . . .
H4 H -0.097990 0.962195 0.732152 0.085 Uiso 1 1 calc R U . . .
C3 C -0.0187(3) 0.7520(3) 0.7877(2) 0.0614(7) Uani 1 1 d . . . . .
H3 H -0.123529 0.750291 0.808292 0.074 Uiso 1 1 calc R U . . .
C17 C 0.7340(4) 0.3764(4) 0.95771(18) 0.0653(8) Uani 1 1 d . . . . .
H17 H 0.774443 0.344703 1.014355 0.078 Uiso 1 1 calc R U . . .
C19 C 0.6942(4) 0.6199(4) 0.98266(18) 0.0687(8) Uani 1 1 d . . . . .
H19A H 0.806284 0.614082 0.976547 0.103 Uiso 1 1 calc R U . . .
H19B H 0.659355 0.592578 1.045699 0.103 Uiso 1 1 calc R U . . .
H19C H 0.622511 0.716572 0.962714 0.103 Uiso 1 1 calc R U . . .
C20 C 0.7743(5) 0.1224(4) 0.9570(2) 0.0896(11) Uani 1 1 d . . . . .
H20A H 0.686503 0.091045 0.956081 0.134 Uiso 1 1 calc R U . . .
H20B H 0.792419 0.114804 1.019363 0.134 Uiso 1 1 calc R U . . .
H20C H 0.874289 0.063242 0.923945 0.134 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 1.8853(16) . ?
Co1 O1 1.8916(15) . ?
Co1 N2 1.8989(18) . ?
Co1 O2 1.8859(15) . ?
Co1 N3 1.9236(18) . ?
Co1 O3 1.8831(16) . ?
N1 C8 1.399(3) . ?
N1 C7 1.290(3) . ?
O1 C1 1.299(2) . ?
N2 C10 1.468(3) . ?
N2 C9 1.344(3) . ?
O2 C16 1.263(3) . ?
N3 C11 1.345(3) . ?
N3 C15 1.329(3) . ?
O3 C18 1.260(3) . ?
C6 C1 1.412(3) . ?
C6 C7 1.414(3) . ?
C6 C5 1.411(3) . ?
C8 C9 1.367(3) . ?
C8 C22 1.413(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(3) . ?
C11 C12 1.368(3) . ?
C9 C21 1.437(3) . ?
C1 C2 1.407(3) . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.362(3) . ?
C21 N4 1.135(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.361(3) . ?
N5 C22 1.138(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.359(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.370(4) . ?
C18 C17 1.381(4) . ?
C18 C19 1.489(4) . ?
C13 H13 0.9300 . ?
C16 C17 1.366(4) . ?
C16 C20 1.503(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
N1 Co1 O1 94.68(6) . . ?
N1 Co1 N2 86.40(7) . . ?
N1 Co1 O2 177.99(6) . . ?
N1 Co1 N3 94.28(7) . . ?
O1 Co1 N2 175.08(7) . . ?
O1 Co1 N3 93.51(7) . . ?
N2 Co1 N3 81.62(7) . . ?
O2 Co1 O1 87.31(7) . . ?
O2 Co1 N2 91.64(7) . . ?
O2 Co1 N3 85.87(7) . . ?
O3 Co1 N1 84.19(7) . . ?
O3 Co1 O1 92.09(7) . . ?
O3 Co1 N2 92.79(7) . . ?
O3 Co1 O2 95.46(7) . . ?
O3 Co1 N3 174.30(7) . . ?
C8 N1 Co1 110.67(13) . . ?
C7 N1 Co1 125.33(14) . . ?
C7 N1 C8 123.55(18) . . ?
C1 O1 Co1 126.11(14) . . ?
C10 N2 Co1 109.24(13) . . ?
C9 N2 Co1 109.64(13) . . ?
C9 N2 C10 114.68(18) . . ?
C16 O2 Co1 123.68(17) . . ?
C11 N3 Co1 113.83(14) . . ?
C15 N3 Co1 126.31(15) . . ?
C15 N3 C11 119.81(19) . . ?
C18 O3 Co1 123.55(18) . . ?
C1 C6 C7 123.47(19) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 117.7(2) . . ?
N1 C8 C22 121.99(19) . . ?
C9 C8 N1 113.91(18) . . ?
C9 C8 C22 123.7(2) . . ?
N2 C10 H10A 110.5 . . ?
N2 C10 H10B 110.5 . . ?
N2 C10 C11 106.09(16) . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
N3 C11 C10 113.58(18) . . ?
N3 C11 C12 121.1(2) . . ?
C12 C11 C10 125.24(19) . . ?
N2 C9 C8 118.86(19) . . ?
N2 C9 C21 120.49(19) . . ?
C8 C9 C21 120.6(2) . . ?
O1 C1 C6 124.00(19) . . ?
O1 C1 C2 118.05(19) . . ?
C2 C1 C6 117.93(19) . . ?
N1 C7 C6 125.04(19) . . ?
N1 C7 H7 117.5 . . ?
C6 C7 H7 117.5 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.2 . . ?
N4 C21 C9 177.4(3) . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.9(2) . . ?
C13 C12 H12 120.6 . . ?
N3 C15 H15 119.3 . . ?
N3 C15 C14 121.3(2) . . ?
C14 C15 H15 119.3 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.1 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C13 C14 H14 120.3 . . ?
N5 C22 C8 175.6(3) . . ?
O3 C18 C17 125.6(2) . . ?
O3 C18 C19 114.9(3) . . ?
C17 C18 C19 119.5(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
O2 C16 C17 125.6(2) . . ?
O2 C16 C20 114.1(3) . . ?
C17 C16 C20 120.3(3) . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C18 C17 H17 117.6 . . ?
C16 C17 C18 124.9(2) . . ?
C16 C17 H17 117.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 C8 C9 4.0(2) . . . . ?
Co1 N1 C8 C22 177.34(17) . . . . ?
Co1 N1 C7 C6 -10.5(3) . . . . ?
Co1 O1 C1 C6 -1.0(3) . . . . ?
Co1 O1 C1 C2 177.93(16) . . . . ?
Co1 N2 C10 C11 39.42(19) . . . . ?
Co1 N2 C9 C8 7.8(2) . . . . ?
Co1 N2 C9 C21 -171.44(16) . . . . ?
Co1 O2 C16 C17 5.6(4) . . . . ?
Co1 O2 C16 C20 -174.8(2) . . . . ?
Co1 N3 C11 C10 -7.2(2) . . . . ?
Co1 N3 C11 C12 175.20(16) . . . . ?
Co1 N3 C15 C14 -175.37(18) . . . . ?
Co1 O3 C18 C17 -6.6(4) . . . . ?
Co1 O3 C18 C19 173.04(18) . . . . ?
N1 Co1 O1 C1 -6.94(17) . . . . ?
N1 Co1 N2 C10 -130.60(14) . . . . ?
N1 Co1 N2 C9 -4.16(14) . . . . ?
N1 Co1 O3 C18 -166.91(19) . . . . ?
N1 C8 C9 N2 -8.1(3) . . . . ?
N1 C8 C9 C21 171.22(18) . . . . ?
O1 Co1 N1 C8 -175.05(13) . . . . ?
O1 Co1 N1 C7 12.50(17) . . . . ?
O1 Co1 O2 C16 -102.50(19) . . . . ?
O1 Co1 O3 C18 98.60(19) . . . . ?
O1 C1 C2 C3 177.7(2) . . . . ?
N2 Co1 N1 C8 0.14(13) . . . . ?
N2 Co1 N1 C7 -172.31(17) . . . . ?
N2 Co1 O2 C16 82.31(19) . . . . ?
N2 Co1 O3 C18 -80.81(19) . . . . ?
N2 C10 C11 N3 -20.7(2) . . . . ?
N2 C10 C11 C12 156.8(2) . . . . ?
O2 Co1 O1 C1 172.77(17) . . . . ?
O2 Co1 N2 C10 49.85(14) . . . . ?
O2 Co1 N2 C9 176.29(14) . . . . ?
O2 Co1 O3 C18 11.10(19) . . . . ?
O2 C16 C17 C18 3.0(5) . . . . ?
N3 Co1 N1 C8 -81.17(13) . . . . ?
N3 Co1 N1 C7 106.38(17) . . . . ?
N3 Co1 O1 C1 -101.54(17) . . . . ?
N3 Co1 N2 C10 -35.74(13) . . . . ?
N3 Co1 N2 C9 90.71(14) . . . . ?
N3 Co1 O2 C16 163.78(19) . . . . ?
N3 C11 C12 C13 0.9(3) . . . . ?
N3 C15 C14 C13 0.1(4) . . . . ?
O3 Co1 N1 C8 93.32(13) . . . . ?
O3 Co1 N1 C7 -79.13(17) . . . . ?
O3 Co1 O1 C1 77.40(17) . . . . ?
O3 Co1 N2 C10 145.40(13) . . . . ?
O3 Co1 N2 C9 -88.16(14) . . . . ?
O3 Co1 O2 C16 -10.66(19) . . . . ?
O3 C18 C17 C16 -2.4(5) . . . . ?
C6 C1 C2 C3 -3.2(4) . . . . ?
C6 C5 C4 C3 -0.3(5) . . . . ?
C8 N1 C7 C6 178.00(19) . . . . ?
C10 N2 C9 C8 131.1(2) . . . . ?
C10 N2 C9 C21 -48.2(3) . . . . ?
C10 C11 C12 C13 -176.4(2) . . . . ?
C11 N3 C15 C14 1.8(3) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C9 N2 C10 C11 -84.1(2) . . . . ?
C1 C6 C7 N1 -0.9(3) . . . . ?
C1 C6 C5 C4 -2.8(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C7 N1 C8 C9 176.57(18) . . . . ?
C7 N1 C8 C22 -10.1(3) . . . . ?
C7 C6 C1 O1 7.1(3) . . . . ?
C7 C6 C1 C2 -171.9(2) . . . . ?
C7 C6 C5 C4 173.7(3) . . . . ?
C15 N3 C11 C10 175.33(18) . . . . ?
C15 N3 C11 C12 -2.3(3) . . . . ?
C15 C14 C13 C12 -1.4(4) . . . . ?
C5 C6 C1 O1 -176.6(2) . . . . ?
C5 C6 C1 C2 4.4(3) . . . . ?
C5 C6 C7 N1 -177.3(2) . . . . ?
C5 C4 C3 C2 1.6(5) . . . . ?
C22 C8 C9 N2 178.71(19) . . . . ?
C22 C8 C9 C21 -2.0(3) . . . . ?
C19 C18 C17 C16 177.9(3) . . . . ?
C20 C16 C17 C18 -176.6(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.000 283.9 93.4 '2 DCM'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_Co-1Br
_audit_block_doi                 10.5517/ccdc.csd.cc2hpkyq
_database_code_depnum_ccdc_archive 'CCDC 2314644'
loop_
_audit_author_name
_audit_author_address
'Kuntal Pal'
;University of Calcutta
India
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Br Co N5 O3'
_chemical_formula_sum            'C22 H17 Br Co N5 O3'
_chemical_formula_weight         538.24
_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'
Br Br -0.2901 2.4595 '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                   11.372(3)
_cell_length_b                   11.481(4)
_cell_length_c                   12.108(4)
_cell_angle_alpha                76.880(5)
_cell_angle_beta                 62.834(4)
_cell_angle_gamma                80.875(5)
_cell_volume                     1367.1(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8093
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.785
_shelx_estimated_absorpt_T_min   0.677
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1060 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.5396. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28210
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_min         1.825
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3581
_reflns_number_total             4970
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4970
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.042
_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)+(0.0364P)²+0.5005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0917
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C2(H2), C20(H20), C17(H17), C3(H3), C14(H14), C16(H16),
 C15(H15)
1.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_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 0.61032(4) 0.68006(3) 0.15817(3) 0.03242(12) Uani 1 1 d . . . . .
Br1 Br 0.00625(3) 0.57817(4) 0.75693(4) 0.07134(16) Uani 1 1 d . . . . .
O1 O 0.42556(18) 0.66752(17) 0.21988(18) 0.0383(5) Uani 1 1 d . . . . .
O3 O 0.64109(19) 0.51133(17) 0.19106(18) 0.0384(5) Uani 1 1 d . . . . .
O2 O 0.62198(19) 0.68684(17) -0.00505(17) 0.0402(5) Uani 1 1 d . . . . .
N1 N 0.6022(2) 0.67343(19) 0.3195(2) 0.0302(5) Uani 1 1 d . . . . .
N3 N 0.5979(2) 0.8541(2) 0.1215(2) 0.0375(6) Uani 1 1 d . . . . .
N2 N 0.7939(2) 0.7056(2) 0.0914(2) 0.0387(6) Uani 1 1 d . . . . .
C7 C 0.4999(3) 0.6474(2) 0.4275(3) 0.0334(6) Uani 1 1 d . . . . .
H7 H 0.512264 0.635139 0.501827 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3704(3) 0.6360(2) 0.4415(3) 0.0329(6) Uani 1 1 d . . . . .
C1 C 0.3388(3) 0.6515(2) 0.3381(3) 0.0339(7) Uani 1 1 d . . . . .
C8 C 0.7275(3) 0.6871(3) 0.3091(3) 0.0358(7) Uani 1 1 d . . . . .
C10 C 0.8216(3) 0.7125(3) 0.1868(3) 0.0377(7) Uani 1 1 d . . . . .
C21 C 0.6525(3) 0.5970(3) -0.0605(3) 0.0374(7) Uani 1 1 d . . . . .
C19 C 0.6776(3) 0.4446(3) 0.1079(3) 0.0393(7) Uani 1 1 d . . . . .
C5 C 0.2684(3) 0.6128(3) 0.5671(3) 0.0400(7) Uani 1 1 d . . . . .
H5 H 0.289475 0.599201 0.636568 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7117(3) 0.9020(3) 0.0310(3) 0.0452(8) Uani 1 1 d . . . . .
C9 C 0.7494(3) 0.6825(3) 0.4166(3) 0.0468(8) Uani 1 1 d . . . . .
C2 C 0.2036(3) 0.6499(3) 0.3659(3) 0.0463(8) Uani 1 1 d . . . . .
H2 H 0.179169 0.663567 0.298458 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6835(3) 0.4806(3) -0.0109(3) 0.0461(8) Uani 1 1 d . . . . .
H20 H 0.710840 0.421749 -0.063201 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4890(3) 0.9261(3) 0.1725(3) 0.0475(8) Uani 1 1 d . . . . .
H17 H 0.410402 0.891714 0.237371 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1404(3) 0.6101(3) 0.5875(3) 0.0467(8) Uani 1 1 d . . . . .
C3 C 0.1077(3) 0.6294(3) 0.4871(3) 0.0494(8) Uani 1 1 d . . . . .
H3 H 0.017919 0.628215 0.502994 0.059 Uiso 1 1 calc R U . . .
C22 C 0.6541(3) 0.6226(3) -0.1879(3) 0.0503(8) Uani 1 1 d . . . . .
H22A H 0.582575 0.682567 -0.188241 0.076 Uiso 1 1 calc R U . . .
H22B H 0.641425 0.548661 -0.207685 0.076 Uiso 1 1 calc R U . . .
H22C H 0.739432 0.653229 -0.251397 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8263(3) 0.8105(3) -0.0118(3) 0.0494(8) Uani 1 1 d . . . . .
H12A H 0.837528 0.787756 -0.090349 0.059 Uiso 1 1 calc R U . . .
H12B H 0.909290 0.843041 -0.027873 0.059 Uiso 1 1 calc R U . . .
N5 N 0.7668(3) 0.6824(3) 0.5024(3) 0.0750(10) Uani 1 1 d . . . . .
C11 C 0.9494(3) 0.7477(3) 0.1620(3) 0.0511(9) Uani 1 1 d . . . . .
N4 N 1.0499(3) 0.7759(3) 0.1411(3) 0.0783(10) Uani 1 1 d . . . . .
C14 C 0.7149(4) 1.0255(3) -0.0128(3) 0.0600(10) Uani 1 1 d . . . . .
H14 H 0.794227 1.059067 -0.077316 0.072 Uiso 1 1 calc R U . . .
C16 C 0.4885(4) 1.0490(3) 0.1329(4) 0.0615(10) Uani 1 1 d . . . . .
H16 H 0.410738 1.098436 0.170652 0.074 Uiso 1 1 calc R U . . .
C15 C 0.6014(5) 1.0984(3) 0.0386(4) 0.0694(12) Uani 1 1 d . . . . .
H15 H 0.601810 1.182398 0.008587 0.083 Uiso 1 1 calc R U . . .
C18 C 0.7147(4) 0.3163(3) 0.1502(4) 0.0643(10) Uani 1 1 d . . . . .
H18A H 0.790590 0.313329 0.168813 0.096 Uiso 1 1 calc R U . . .
H18B H 0.738287 0.270341 0.083180 0.096 Uiso 1 1 calc R U . . .
H18C H 0.639462 0.281696 0.226311 0.096 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 O1 1.8993(19) . ?
Co1 O3 1.896(2) . ?
Co1 O2 1.904(2) . ?
Co1 N1 1.897(2) . ?
Co1 N3 1.943(2) . ?
Co1 N2 1.909(2) . ?
Br1 C4 1.910(3) . ?
O1 C1 1.306(3) . ?
O3 C19 1.281(3) . ?
O2 C21 1.274(3) . ?
N1 C7 1.303(3) . ?
N1 C8 1.403(3) . ?
N3 C13 1.355(4) . ?
N3 C17 1.344(4) . ?
N2 C10 1.350(4) . ?
N2 C12 1.478(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.427(4) . ?
C6 C1 1.421(4) . ?
C6 C5 1.425(4) . ?
C1 C2 1.418(4) . ?
C8 C10 1.370(4) . ?
C8 C9 1.421(4) . ?
C10 C11 1.448(4) . ?
C21 C20 1.396(4) . ?
C21 C22 1.496(4) . ?
C19 C20 1.376(4) . ?
C19 C18 1.507(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.364(4) . ?
C13 C12 1.505(4) . ?
C13 C14 1.396(4) . ?
C9 N5 1.144(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.365(4) . ?
C20 H20 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.383(4) . ?
C4 C3 1.389(4) . ?
C3 H3 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 N4 1.136(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.368(5) . ?
C15 H15 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O2 86.45(8) . . ?
O1 Co1 N3 93.96(9) . . ?
O1 Co1 N2 175.53(9) . . ?
O3 Co1 O1 92.00(8) . . ?
O3 Co1 O2 95.46(8) . . ?
O3 Co1 N1 84.47(9) . . ?
O3 Co1 N3 173.92(9) . . ?
O3 Co1 N2 92.40(9) . . ?
O2 Co1 N3 86.12(9) . . ?
O2 Co1 N2 92.37(9) . . ?
N1 Co1 O1 94.63(8) . . ?
N1 Co1 O2 178.92(9) . . ?
N1 Co1 N3 93.83(9) . . ?
N1 Co1 N2 86.56(10) . . ?
N2 Co1 N3 81.66(10) . . ?
C1 O1 Co1 126.23(17) . . ?
C19 O3 Co1 123.65(19) . . ?
C21 O2 Co1 124.46(19) . . ?
C7 N1 Co1 126.03(19) . . ?
C7 N1 C8 123.0(2) . . ?
C8 N1 Co1 110.64(17) . . ?
C13 N3 Co1 113.7(2) . . ?
C17 N3 Co1 126.4(2) . . ?
C17 N3 C13 119.8(3) . . ?
C10 N2 Co1 108.93(18) . . ?
C10 N2 C12 115.5(2) . . ?
C12 N2 Co1 108.92(18) . . ?
N1 C7 H7 117.8 . . ?
N1 C7 C6 124.4(3) . . ?
C6 C7 H7 117.8 . . ?
C1 C6 C7 123.4(2) . . ?
C1 C6 C5 119.6(2) . . ?
C5 C6 C7 116.9(2) . . ?
O1 C1 C6 124.4(2) . . ?
O1 C1 C2 118.1(3) . . ?
C2 C1 C6 117.5(3) . . ?
N1 C8 C9 122.0(2) . . ?
C10 C8 N1 113.5(2) . . ?
C10 C8 C9 124.4(3) . . ?
N2 C10 C8 119.8(2) . . ?
N2 C10 C11 120.9(3) . . ?
C8 C10 C11 119.3(3) . . ?
O2 C21 C20 124.8(3) . . ?
O2 C21 C22 115.4(3) . . ?
C20 C21 C22 119.7(3) . . ?
O3 C19 C20 125.8(3) . . ?
O3 C19 C18 114.1(3) . . ?
C20 C19 C18 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
N3 C13 C12 113.5(3) . . ?
N3 C13 C14 120.2(3) . . ?
C14 C13 C12 126.3(3) . . ?
N5 C9 C8 178.0(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C21 C20 H20 117.5 . . ?
C19 C20 C21 125.1(3) . . ?
C19 C20 H20 117.5 . . ?
N3 C17 H17 119.1 . . ?
N3 C17 C16 121.7(3) . . ?
C16 C17 H17 119.1 . . ?
C5 C4 Br1 118.9(3) . . ?
C5 C4 C3 120.9(3) . . ?
C3 C4 Br1 120.2(2) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C12 C13 106.3(2) . . ?
N2 C12 H12A 110.5 . . ?
N2 C12 H12B 110.5 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
N4 C11 C10 179.2(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C17 C16 H16 120.4 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 O1 C1 C6 -2.6(4) . . . . ?
Co1 O1 C1 C2 177.08(19) . . . . ?
Co1 O3 C19 C20 -8.9(4) . . . . ?
Co1 O3 C19 C18 171.7(2) . . . . ?
Co1 O2 C21 C20 -0.8(4) . . . . ?
Co1 O2 C21 C22 179.29(18) . . . . ?
Co1 N1 C7 C6 -9.4(4) . . . . ?
Co1 N1 C8 C10 5.6(3) . . . . ?
Co1 N1 C8 C9 -178.4(2) . . . . ?
Co1 N3 C13 C12 -5.8(3) . . . . ?
Co1 N3 C13 C14 174.7(2) . . . . ?
Co1 N3 C17 C16 -175.1(2) . . . . ?
Co1 N2 C10 C8 7.9(3) . . . . ?
Co1 N2 C10 C11 -171.6(2) . . . . ?
Co1 N2 C12 C13 40.4(3) . . . . ?
Br1 C4 C3 C2 -178.8(2) . . . . ?
O1 Co1 O3 C19 96.0(2) . . . . ?
O1 Co1 N1 C7 9.9(2) . . . . ?
O1 Co1 N1 C8 -176.91(18) . . . . ?
O1 C1 C2 C3 177.6(3) . . . . ?
O3 Co1 O1 C1 80.5(2) . . . . ?
O3 Co1 N1 C7 -81.6(2) . . . . ?
O3 Co1 N1 C8 91.52(18) . . . . ?
O3 C19 C20 C21 1.1(5) . . . . ?
O2 Co1 O1 C1 175.9(2) . . . . ?
O2 Co1 O3 C19 9.3(2) . . . . ?
O2 C21 C20 C19 4.3(5) . . . . ?
N1 Co1 O1 C1 -4.1(2) . . . . ?
N1 Co1 O3 C19 -169.6(2) . . . . ?
N1 C7 C6 C1 0.3(4) . . . . ?
N1 C7 C6 C5 -177.0(3) . . . . ?
N1 C8 C10 N2 -9.2(4) . . . . ?
N1 C8 C10 C11 170.2(3) . . . . ?
N3 Co1 O1 C1 -98.3(2) . . . . ?
N3 Co1 N1 C7 104.2(2) . . . . ?
N3 Co1 N1 C8 -82.62(19) . . . . ?
N3 C13 C12 N2 -22.1(3) . . . . ?
N3 C13 C14 C15 1.1(5) . . . . ?
N3 C17 C16 C15 0.6(5) . . . . ?
N2 Co1 O3 C19 -83.3(2) . . . . ?
N2 Co1 N1 C7 -174.4(2) . . . . ?
N2 Co1 N1 C8 -1.23(18) . . . . ?
C7 N1 C8 C10 179.0(3) . . . . ?
C7 N1 C8 C9 -5.0(4) . . . . ?
C7 C6 C1 O1 6.1(4) . . . . ?
C7 C6 C1 C2 -173.6(3) . . . . ?
C7 C6 C5 C4 175.0(3) . . . . ?
C6 C1 C2 C3 -2.7(4) . . . . ?
C6 C5 C4 Br1 179.8(2) . . . . ?
C6 C5 C4 C3 0.2(5) . . . . ?
C1 C6 C5 C4 -2.5(4) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C8 N1 C7 C6 178.3(2) . . . . ?
C10 N2 C12 C13 -82.6(3) . . . . ?
C5 C6 C1 O1 -176.7(3) . . . . ?
C5 C6 C1 C2 3.7(4) . . . . ?
C5 C4 C3 C2 0.8(5) . . . . ?
C13 N3 C17 C16 1.6(4) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C9 C8 C10 N2 174.9(3) . . . . ?
C9 C8 C10 C11 -5.7(5) . . . . ?
C17 N3 C13 C12 177.1(3) . . . . ?
C17 N3 C13 C14 -2.4(4) . . . . ?
C17 C16 C15 C14 -1.9(5) . . . . ?
C22 C21 C20 C19 -175.8(3) . . . . ?
C12 N2 C10 C8 130.8(3) . . . . ?
C12 N2 C10 C11 -48.6(4) . . . . ?
C12 C13 C14 C15 -178.4(3) . . . . ?
C14 C13 C12 N2 157.4(3) . . . . ?
C18 C19 C20 C21 -179.5(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.213 0.000 -0.904 386.3 82.9 '2 DCM'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
