# 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. 
# 
#######################################################################

data_ss345
_database_code_depnum_ccdc_archive 'CCDC 2286461'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.69(I), C21 H23 B Co N9 O3, 0.31(Cl), C6 H6'
_chemical_formula_sum            'C27 H29 B Cl0.31 Co I0.69 N9 O3'
_chemical_formula_weight         695.88
_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'
B B 0.0013 0.0007 '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'
I I -0.4742 1.8119 '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                   8.2151(6)
_cell_length_b                   13.4093(10)
_cell_length_c                   14.4049(10)
_cell_angle_alpha                87.978(2)
_cell_angle_beta                 74.903(2)
_cell_angle_gamma                75.460(2)
_cell_volume                     1482.22(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4033
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.73
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.684
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.5758
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0754 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.7711.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17100
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.182
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5219
_reflns_number_total             7141
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         7141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.026
_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)+(0.0381P)²+0.1372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(I1)=1-FVAR(1)
 Sof(Cl1)=FVAR(1)
3.a Riding coordinates:
 N3(H3), N6(H6), N9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C1S(H1S), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S),
  C6S(H6S)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.30901(7) 0.91582(3) 1.04116(4) 0.02196(14) Uani 0.690(2) 1 d . . P A 1
Co1 Co 0.51528(5) 0.61301(3) 0.79483(3) 0.01881(13) Uani 1 1 d . . . . .
Cl1 Cl 0.3413(13) 0.9092(9) 1.0139(9) 0.163(8) Uani 0.310(2) 1 d . . P A 2
O1 O 0.7123(3) 0.50105(15) 0.59450(15) 0.0234(5) Uani 1 1 d . . . . .
O2 O 0.4462(2) 0.44697(15) 0.67450(15) 0.0231(5) Uani 1 1 d . . . . .
O3 O 0.7127(3) 0.38584(15) 0.73160(15) 0.0250(5) Uani 1 1 d . . . . .
N1 N 0.6732(3) 0.59103(18) 0.64897(18) 0.0208(5) Uani 1 1 d . . . . .
N2 N 0.5890(3) 0.75572(19) 0.75619(19) 0.0235(6) Uani 1 1 d . . . . .
N3 N 0.5684(3) 0.84973(19) 0.7956(2) 0.0301(6) Uani 1 1 d . . . . .
H3 H 0.4987 0.8632 0.8503 0.036 Uiso 1 1 d R U . . .
N4 N 0.3726(3) 0.53411(18) 0.73379(17) 0.0206(5) Uani 1 1 d . . . . .
N5 N 0.2469(3) 0.69789(19) 0.84406(18) 0.0221(6) Uani 1 1 d . . . . .
N6 N 0.1490(3) 0.7834(2) 0.89684(19) 0.0269(6) Uani 1 1 d . . . . .
H6 H 0.1887 0.8166 0.9365 0.032 Uiso 1 1 d R U . . .
N7 N 0.6752(3) 0.46248(18) 0.80033(18) 0.0212(5) Uani 1 1 d . . . . .
N8 N 0.5936(3) 0.60997(19) 0.92773(18) 0.0225(6) Uani 1 1 d . . . . .
N9 N 0.5748(3) 0.6709(2) 1.00406(19) 0.0288(6) Uani 1 1 d . . . . .
H9 H 0.5222 0.7306 1.0091 0.035 Uiso 1 1 d R U . . .
C1 C 0.7367(4) 0.6634(2) 0.6058(2) 0.0220(6) Uani 1 1 d . . . . .
C2 C 0.6909(4) 0.7569(2) 0.6668(2) 0.0229(7) Uani 1 1 d . . . . .
C3 C 0.7345(5) 0.8515(3) 0.6504(3) 0.0354(8) Uani 1 1 d . . . . .
H3A H 0.8052 0.8719 0.5934 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6537(5) 0.9080(3) 0.7340(3) 0.0390(9) Uani 1 1 d . . . . .
H4 H 0.6573 0.9765 0.7463 0.047 Uiso 1 1 calc R U . . .
C5 C 0.8458(4) 0.6559(2) 0.5046(2) 0.0325(8) Uani 1 1 d . . . . .
H5A H 0.9437 0.5946 0.4961 0.049 Uiso 1 1 calc R U . . .
H5B H 0.8904 0.7175 0.4906 0.049 Uiso 1 1 calc R U . . .
H5C H 0.7750 0.6505 0.4607 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2077(4) 0.5695(2) 0.7451(2) 0.0204(6) Uani 1 1 d . . . . .
C7 C 0.1350(4) 0.6616(2) 0.8087(2) 0.0213(6) Uani 1 1 d . . . . .
C8 C -0.0340(4) 0.7247(3) 0.8404(2) 0.0306(8) Uani 1 1 d . . . . .
H8 H -0.1365 0.7163 0.8261 0.037 Uiso 1 1 calc R U . . .
C9 C -0.0199(4) 0.8013(3) 0.8964(3) 0.0352(8) Uani 1 1 d . . . . .
H9A H -0.1122 0.8567 0.9288 0.042 Uiso 1 1 calc R U . . .
C10 C 0.0994(4) 0.5242(3) 0.6993(2) 0.0310(8) Uani 1 1 d . . . . .
H10A H 0.1250 0.4496 0.7081 0.046 Uiso 1 1 calc R U . . .
H10B H 0.1257 0.5380 0.6305 0.046 Uiso 1 1 calc R U . . .
H10C H -0.0241 0.5551 0.7293 0.046 Uiso 1 1 calc R U . . .
C11 C 0.7545(4) 0.4386(2) 0.8674(2) 0.0218(6) Uani 1 1 d . . . . .
C12 C 0.7083(4) 0.5215(2) 0.9396(2) 0.0215(6) Uani 1 1 d . . . . .
C13 C 0.7615(4) 0.5279(2) 1.0233(2) 0.0277(7) Uani 1 1 d . . . . .
H13 H 0.8417 0.4770 1.0479 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6716(4) 0.6246(3) 1.0623(2) 0.0312(8) Uani 1 1 d . . . . .
H14 H 0.6774 0.6533 1.1203 0.037 Uiso 1 1 calc R U . . .
C15 C 0.8806(4) 0.3383(3) 0.8723(3) 0.0321(8) Uani 1 1 d . . . . .
H15A H 0.8184 0.2838 0.8867 0.048 Uiso 1 1 calc R U . . .
H15B H 0.9381 0.3429 0.9231 0.048 Uiso 1 1 calc R U . . .
H15C H 0.9681 0.3223 0.8104 0.048 Uiso 1 1 calc R U . . .
C16 C 0.6981(3) 0.3177(2) 0.5758(2) 0.0209(6) Uani 1 1 d . . . . .
C17 C 0.6543(4) 0.3230(2) 0.4883(2) 0.0246(7) Uani 1 1 d . . . . .
H17 H 0.5930 0.3872 0.4698 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6974(4) 0.2372(3) 0.4273(2) 0.0296(7) Uani 1 1 d . . . . .
H18 H 0.6665 0.2432 0.3678 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7863(4) 0.1420(3) 0.4535(2) 0.0348(8) Uani 1 1 d . . . . .
H19 H 0.8150 0.0828 0.4124 0.042 Uiso 1 1 calc R U . . .
C20 C 0.8324(4) 0.1344(2) 0.5397(2) 0.0318(8) Uani 1 1 d . . . . .
H20 H 0.8936 0.0699 0.5578 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7890(4) 0.2214(2) 0.6004(2) 0.0263(7) Uani 1 1 d . . . . .
H21 H 0.8215 0.2152 0.6594 0.032 Uiso 1 1 calc R U . . .
B1 B 0.6416(4) 0.4166(3) 0.6467(3) 0.0211(7) Uani 1 1 d . . . . .
C1S C 0.3577(5) 0.1648(3) 0.6665(3) 0.0437(9) Uani 1 1 d . . . . .
H1S H 0.4223 0.1916 0.6111 0.052 Uiso 1 1 calc R U . . .
C2S C 0.2255(5) 0.1209(3) 0.6603(3) 0.0504(11) Uani 1 1 d . . . . .
H2S H 0.1978 0.1186 0.6005 0.060 Uiso 1 1 calc R U . . .
C3S C 0.1328(5) 0.0800(3) 0.7408(3) 0.0437(9) Uani 1 1 d . . . . .
H3S H 0.0417 0.0502 0.7361 0.052 Uiso 1 1 calc R U . . .
C4S C 0.1732(5) 0.0826(3) 0.8267(3) 0.0375(8) Uani 1 1 d . . . . .
H4S H 0.1118 0.0536 0.8817 0.045 Uiso 1 1 calc R U . . .
C5S C 0.3035(5) 0.1276(3) 0.8332(3) 0.0431(9) Uani 1 1 d . . . . .
H5S H 0.3311 0.1302 0.8930 0.052 Uiso 1 1 calc R U . . .
C6S C 0.3945(5) 0.1692(3) 0.7530(3) 0.0421(9) Uani 1 1 d . . . . .
H6S H 0.4830 0.2010 0.7582 0.051 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 2.149(3) . ?
Co1 N2 2.161(3) . ?
Co1 N4 2.120(2) . ?
Co1 N5 2.155(2) . ?
Co1 N7 2.126(2) . ?
Co1 N8 2.169(2) . ?
O1 N1 1.384(3) . ?
O1 B1 1.493(4) . ?
O2 N4 1.381(3) . ?
O2 B1 1.500(4) . ?
O3 N7 1.373(3) . ?
O3 B1 1.490(4) . ?
N1 C1 1.282(4) . ?
N2 N3 1.354(3) . ?
N2 C2 1.342(4) . ?
N3 H3 0.8394 . ?
N3 C4 1.338(4) . ?
N4 C6 1.286(4) . ?
N5 N6 1.349(3) . ?
N5 C7 1.351(4) . ?
N6 H6 0.9043 . ?
N6 C9 1.350(4) . ?
N7 C11 1.289(4) . ?
N8 N9 1.346(3) . ?
N8 C12 1.354(4) . ?
N9 H9 0.8038 . ?
N9 C14 1.336(4) . ?
C1 C2 1.468(4) . ?
C1 C5 1.490(4) . ?
C2 C3 1.398(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.364(5) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.466(4) . ?
C6 C10 1.483(4) . ?
C7 C8 1.400(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(5) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.458(4) . ?
C11 C15 1.489(4) . ?
C12 C13 1.398(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.393(4) . ?
C16 C21 1.405(4) . ?
C16 B1 1.599(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.397(4) . ?
C21 H21 0.9500 . ?
C1S H1S 0.9500 . ?
C1S C2S 1.382(5) . ?
C1S C6S 1.362(5) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.389(5) . ?
C3S H3S 0.9500 . ?
C3S C4S 1.366(5) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.378(5) . ?
C5S H5S 0.9500 . ?
C5S C6S 1.385(5) . ?
C6S H6S 0.9500 . ?

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 N2 73.56(9) . . ?
N1 Co1 N5 127.18(9) . . ?
N1 Co1 N8 129.41(9) . . ?
N2 Co1 N8 91.37(9) . . ?
N4 Co1 N1 79.72(9) . . ?
N4 Co1 N2 130.53(9) . . ?
N4 Co1 N5 74.31(9) . . ?
N4 Co1 N7 83.56(9) . . ?
N4 Co1 N8 136.89(9) . . ?
N5 Co1 N2 89.78(9) . . ?
N5 Co1 N8 99.93(9) . . ?
N7 Co1 N1 79.47(9) . . ?
N7 Co1 N2 129.46(9) . . ?
N7 Co1 N5 139.75(10) . . ?
N7 Co1 N8 73.99(9) . . ?
N1 O1 B1 114.5(2) . . ?
N4 O2 B1 114.7(2) . . ?
N7 O3 B1 115.2(2) . . ?
O1 N1 Co1 123.96(17) . . ?
C1 N1 Co1 120.9(2) . . ?
C1 N1 O1 115.1(2) . . ?
N3 N2 Co1 139.7(2) . . ?
C2 N2 Co1 115.5(2) . . ?
C2 N2 N3 104.8(2) . . ?
N2 N3 H3 116.2 . . ?
C4 N3 N2 111.7(3) . . ?
C4 N3 H3 131.8 . . ?
O2 N4 Co1 124.33(16) . . ?
C6 N4 Co1 121.0(2) . . ?
C6 N4 O2 114.6(2) . . ?
N6 N5 Co1 139.99(19) . . ?
N6 N5 C7 105.3(2) . . ?
C7 N5 Co1 114.53(19) . . ?
N5 N6 H6 123.1 . . ?
C9 N6 N5 111.6(3) . . ?
C9 N6 H6 124.3 . . ?
O3 N7 Co1 124.20(17) . . ?
C11 N7 Co1 121.2(2) . . ?
C11 N7 O3 114.5(2) . . ?
N9 N8 Co1 140.93(19) . . ?
N9 N8 C12 104.8(2) . . ?
C12 N8 Co1 114.11(19) . . ?
N8 N9 H9 122.9 . . ?
C14 N9 N8 112.0(3) . . ?
C14 N9 H9 124.6 . . ?
N1 C1 C2 112.8(3) . . ?
N1 C1 C5 124.8(3) . . ?
C2 C1 C5 122.4(3) . . ?
N2 C2 C1 117.3(3) . . ?
N2 C2 C3 110.7(3) . . ?
C3 C2 C1 132.0(3) . . ?
C2 C3 H3A 127.4 . . ?
C4 C3 C2 105.1(3) . . ?
C4 C3 H3A 127.4 . . ?
N3 C4 C3 107.7(3) . . ?
N3 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 112.7(3) . . ?
N4 C6 C10 124.9(3) . . ?
C7 C6 C10 122.5(3) . . ?
N5 C7 C6 117.3(2) . . ?
N5 C7 C8 110.4(3) . . ?
C8 C7 C6 132.2(3) . . ?
C7 C8 H8 127.4 . . ?
C9 C8 C7 105.2(3) . . ?
C9 C8 H8 127.4 . . ?
N6 C9 C8 107.5(3) . . ?
N6 C9 H9A 126.3 . . ?
C8 C9 H9A 126.3 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 112.6(3) . . ?
N7 C11 C15 124.8(3) . . ?
C12 C11 C15 122.6(3) . . ?
N8 C12 C11 117.8(3) . . ?
N8 C12 C13 110.8(3) . . ?
C13 C12 C11 131.4(3) . . ?
C12 C13 H13 127.8 . . ?
C14 C13 C12 104.5(3) . . ?
C14 C13 H13 127.8 . . ?
N9 C14 C13 108.0(3) . . ?
N9 C14 H14 126.0 . . ?
C13 C14 H14 126.0 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.3(3) . . ?
C17 C16 B1 121.3(3) . . ?
C21 C16 B1 121.4(3) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
O1 B1 O2 110.6(2) . . ?
O1 B1 C16 109.0(2) . . ?
O2 B1 C16 106.2(2) . . ?
O3 B1 O1 111.4(2) . . ?
O3 B1 O2 111.7(3) . . ?
O3 B1 C16 107.7(2) . . ?
C2S C1S H1S 120.4 . . ?
C6S C1S H1S 120.4 . . ?
C6S C1S C2S 119.3(4) . . ?
C1S C2S H2S 119.7 . . ?
C1S C2S C3S 120.5(4) . . ?
C3S C2S H2S 119.7 . . ?
C2S C3S H3S 120.1 . . ?
C4S C3S C2S 119.8(4) . . ?
C4S C3S H3S 120.1 . . ?
C3S C4S H4S 120.2 . . ?
C3S C4S C5S 119.7(4) . . ?
C5S C4S H4S 120.2 . . ?
C4S C5S H5S 119.8 . . ?
C4S C5S C6S 120.3(4) . . ?
C6S C5S H5S 119.8 . . ?
C1S C6S C5S 120.4(4) . . ?
C1S C6S H6S 119.8 . . ?
C5S C6S H6S 119.8 . . ?

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 C1 C2 0.7(3) . . . . ?
Co1 N1 C1 C5 -179.3(2) . . . . ?
Co1 N2 N3 C4 177.9(2) . . . . ?
Co1 N2 C2 C1 1.3(3) . . . . ?
Co1 N2 C2 C3 -178.3(2) . . . . ?
Co1 N4 C6 C7 -4.5(3) . . . . ?
Co1 N4 C6 C10 175.2(2) . . . . ?
Co1 N5 N6 C9 175.3(3) . . . . ?
Co1 N5 C7 C6 1.7(3) . . . . ?
Co1 N5 C7 C8 -176.8(2) . . . . ?
Co1 N7 C11 C12 5.2(3) . . . . ?
Co1 N7 C11 C15 -174.5(2) . . . . ?
Co1 N8 N9 C14 -174.8(2) . . . . ?
Co1 N8 C12 C11 -4.1(3) . . . . ?
Co1 N8 C12 C13 176.0(2) . . . . ?
O1 N1 C1 C2 179.9(2) . . . . ?
O1 N1 C1 C5 -0.1(4) . . . . ?
O2 N4 C6 C7 179.8(2) . . . . ?
O2 N4 C6 C10 -0.5(4) . . . . ?
O3 N7 C11 C12 -178.9(2) . . . . ?
O3 N7 C11 C15 1.3(4) . . . . ?
N1 O1 B1 O2 64.1(3) . . . . ?
N1 O1 B1 O3 -60.8(3) . . . . ?
N1 O1 B1 C16 -179.5(2) . . . . ?
N1 C1 C2 N2 -1.3(4) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
N2 N3 C4 C3 -0.1(4) . . . . ?
N2 C2 C3 C4 -0.3(4) . . . . ?
N3 N2 C2 C1 179.8(2) . . . . ?
N3 N2 C2 C3 0.2(3) . . . . ?
N4 O2 B1 O1 -59.8(3) . . . . ?
N4 O2 B1 O3 64.9(3) . . . . ?
N4 O2 B1 C16 -177.9(2) . . . . ?
N4 C6 C7 N5 1.7(4) . . . . ?
N4 C6 C7 C8 179.8(3) . . . . ?
N5 N6 C9 C8 -0.4(4) . . . . ?
N5 C7 C8 C9 0.2(4) . . . . ?
N6 N5 C7 C6 178.0(2) . . . . ?
N6 N5 C7 C8 -0.5(3) . . . . ?
N7 O3 B1 O1 60.7(3) . . . . ?
N7 O3 B1 O2 -63.5(3) . . . . ?
N7 O3 B1 C16 -179.8(2) . . . . ?
N7 C11 C12 N8 -0.5(4) . . . . ?
N7 C11 C12 C13 179.4(3) . . . . ?
N8 N9 C14 C13 0.5(4) . . . . ?
N8 C12 C13 C14 0.7(4) . . . . ?
N9 N8 C12 C11 179.5(2) . . . . ?
N9 N8 C12 C13 -0.4(3) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C2 N2 N3 C4 -0.1(3) . . . . ?
C2 C3 C4 N3 0.2(4) . . . . ?
C5 C1 C2 N2 178.7(3) . . . . ?
C5 C1 C2 C3 -1.8(5) . . . . ?
C6 C7 C8 C9 -178.0(3) . . . . ?
C7 N5 N6 C9 0.6(3) . . . . ?
C7 C8 C9 N6 0.1(4) . . . . ?
C10 C6 C7 N5 -178.1(3) . . . . ?
C10 C6 C7 C8 0.0(5) . . . . ?
C11 C12 C13 C14 -179.2(3) . . . . ?
C12 N8 N9 C14 0.0(3) . . . . ?
C12 C13 C14 N9 -0.7(4) . . . . ?
C15 C11 C12 N8 179.3(3) . . . . ?
C15 C11 C12 C13 -0.8(5) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C16 C21 C20 -0.4(4) . . . . ?
C17 C16 B1 O1 -57.4(3) . . . . ?
C17 C16 B1 O2 61.7(3) . . . . ?
C17 C16 B1 O3 -178.4(3) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C19 C20 C21 C16 0.1(5) . . . . ?
C21 C16 C17 C18 0.1(4) . . . . ?
C21 C16 B1 O1 124.6(3) . . . . ?
C21 C16 B1 O2 -116.2(3) . . . . ?
C21 C16 B1 O3 3.7(4) . . . . ?
B1 O1 N1 Co1 -2.5(3) . . . . ?
B1 O1 N1 C1 178.3(2) . . . . ?
B1 O2 N4 Co1 -6.2(3) . . . . ?
B1 O2 N4 C6 169.4(2) . . . . ?
B1 O3 N7 Co1 3.7(3) . . . . ?
B1 O3 N7 C11 -172.0(3) . . . . ?
B1 C16 C17 C18 -177.9(3) . . . . ?
B1 C16 C21 C20 177.6(3) . . . . ?
C1S C2S C3S C4S -0.3(6) . . . . ?
C2S C1S C6S C5S 1.7(6) . . . . ?
C2S C3S C4S C5S 1.2(6) . . . . ?
C3S C4S C5S C6S -0.6(6) . . . . ?
C4S C5S C6S C1S -0.9(6) . . . . ?
C6S C1S C2S C3S -1.1(6) . . . . ?

_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_AB384
_database_code_depnum_ccdc_archive 'CCDC 2286462'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 B Co N9 O3, Cl, C3 H6 O'
_chemical_formula_sum            'C24 H29 B Cl Co N9 O4'
_chemical_formula_weight         612.75
_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'
B B 0.0013 0.0007 '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'
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                   8.096(2)
_cell_length_b                   10.116(3)
_cell_length_c                   18.105(5)
_cell_angle_alpha                78.627(6)
_cell_angle_beta                 77.176(6)
_cell_angle_gamma                80.835(6)
_cell_volume                     1406.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      29.86
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0816 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.7995.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.1114
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15903
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                4758
_reflns_number_total             7435
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.217
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         7435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.079
_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)+(0.0999P)²+2.9917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2092
_refine_ls_wR_factor_ref         0.2351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3), N6(H6), N9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C2S(H2SA,H2SB,
 H2SC), C3S(H3SA,H3SB,H3SC)
;
_atom_sites_solution_hydrogens   mixed
_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 0.46973(8) 0.65548(6) 0.71544(4) 0.01667(18) Uani 1 1 d . . . . .
O1 O 0.6864(4) 0.6009(3) 0.55767(19) 0.0215(7) Uani 1 1 d . . . . .
O2 O 0.6440(4) 0.8442(3) 0.56837(18) 0.0204(7) Uani 1 1 d . . . . .
O3 O 0.4073(4) 0.7392(4) 0.54745(19) 0.0233(7) Uani 1 1 d . . . . .
N1 N 0.6524(5) 0.5548(4) 0.6357(2) 0.0171(8) Uani 1 1 d . . . . .
N2 N 0.5773(5) 0.4736(4) 0.7823(2) 0.0203(8) Uani 1 1 d . . . . .
N3 N 0.5737(5) 0.4137(4) 0.8562(2) 0.0224(9) Uani 1 1 d . . . . .
H3 H 0.5102 0.4455 0.8927 0.027 Uiso 1 1 d R U . . .
N4 N 0.5967(5) 0.8250(4) 0.6472(2) 0.0174(8) Uani 1 1 d . . . . .
N5 N 0.5021(5) 0.7759(4) 0.7948(2) 0.0209(8) Uani 1 1 d . . . . .
N6 N 0.4701(5) 0.7730(4) 0.8715(2) 0.0246(9) Uani 1 1 d . . . . .
H6 H 0.4286 0.7009 0.9106 0.030 Uiso 1 1 d R U . . .
N7 N 0.3343(5) 0.7023(4) 0.6231(2) 0.0195(8) Uani 1 1 d . . . . .
N8 N 0.2097(5) 0.6256(4) 0.7684(2) 0.0190(8) Uani 1 1 d . . . . .
N9 N 0.1141(5) 0.5809(4) 0.8370(2) 0.0233(9) Uani 1 1 d . . . . .
H9 H 0.1568 0.5564 0.8810 0.028 Uiso 1 1 d R U . . .
C1 C 0.7417(6) 0.4414(5) 0.6580(3) 0.0202(9) Uani 1 1 d . . . . .
C2 C 0.7023(6) 0.3975(5) 0.7410(3) 0.0197(9) Uani 1 1 d . . . . .
C3 C 0.7759(6) 0.2892(5) 0.7894(3) 0.0239(10) Uani 1 1 d . . . . .
H3A H 0.8657 0.2209 0.7748 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6900(7) 0.3032(5) 0.8625(3) 0.0263(11) Uani 1 1 d . . . . .
H4 H 0.7091 0.2456 0.9088 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8754(8) 0.3647(6) 0.6061(3) 0.0347(13) Uani 1 1 d . . . . .
H5A H 0.8207 0.3165 0.5779 0.052 Uiso 1 1 calc R U . . .
H5B H 0.9471 0.2990 0.6367 0.052 Uiso 1 1 calc R U . . .
H5C H 0.9461 0.4282 0.5695 0.052 Uiso 1 1 calc R U . . .
C6 C 0.6264(6) 0.9178(5) 0.6800(3) 0.0205(9) Uani 1 1 d . . . . .
C7 C 0.5748(6) 0.8903(5) 0.7638(3) 0.0215(10) Uani 1 1 d . . . . .
C8 C 0.5862(7) 0.9617(6) 0.8214(3) 0.0298(12) Uani 1 1 d . . . . .
H8 H 0.6311 1.0453 0.8150 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5175(7) 0.8831(6) 0.8890(3) 0.0296(12) Uani 1 1 d . . . . .
H9A H 0.5057 0.9030 0.9392 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7045(7) 1.0437(5) 0.6400(3) 0.0268(11) Uani 1 1 d . . . . .
H10A H 0.8236 1.0334 0.6458 0.040 Uiso 1 1 calc R U . . .
H10B H 0.6411 1.1216 0.6628 0.040 Uiso 1 1 calc R U . . .
H10C H 0.6999 1.0585 0.5854 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1701(6) 0.7044(5) 0.6377(3) 0.0204(10) Uani 1 1 d . . . . .
C12 C 0.1020(5) 0.6587(5) 0.7193(3) 0.0193(9) Uani 1 1 d . . . . .
C13 C -0.0660(6) 0.6370(5) 0.7577(3) 0.0233(10) Uani 1 1 d . . . . .
H13 H -0.1665 0.6534 0.7368 0.028 Uiso 1 1 calc R U . . .
C14 C -0.0501(6) 0.5863(5) 0.8331(3) 0.0247(10) Uani 1 1 d . . . . .
H14 H -0.1398 0.5601 0.8746 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0599(7) 0.7443(7) 0.5798(3) 0.0377(14) Uani 1 1 d . . . . .
H15A H 0.1089 0.8143 0.5388 0.057 Uiso 1 1 calc R U . . .
H15B H -0.0544 0.7804 0.6044 0.057 Uiso 1 1 calc R U . . .
H15C H 0.0522 0.6648 0.5580 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6585(6) 0.7726(5) 0.4412(3) 0.0201(9) Uani 1 1 d . . . . .
C17 C 0.6519(7) 0.6758(5) 0.3953(3) 0.0245(10) Uani 1 1 d . . . . .
H17 H 0.6144 0.5907 0.4196 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6989(7) 0.7022(6) 0.3159(3) 0.0299(12) Uani 1 1 d . . . . .
H18 H 0.6924 0.6357 0.2865 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7556(7) 0.8257(6) 0.2791(3) 0.0302(12) Uani 1 1 d . . . . .
H19 H 0.7880 0.8439 0.2247 0.036 Uiso 1 1 calc R U . . .
C20 C 0.7645(6) 0.9218(5) 0.3225(3) 0.0273(11) Uani 1 1 d . . . . .
H20 H 0.8027 1.0065 0.2976 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7178(6) 0.8950(5) 0.4025(3) 0.0226(10) Uani 1 1 d . . . . .
H21 H 0.7265 0.9617 0.4313 0.027 Uiso 1 1 calc R U . . .
B1 B 0.5976(6) 0.7395(5) 0.5327(3) 0.0191(10) Uani 1 1 d . . . . .
Cl1 Cl 0.28029(15) 0.54012(13) 0.97970(7) 0.0265(3) Uani 1 1 d . . . . .
O1S O 0.7876(6) 0.0256(4) 0.9731(3) 0.0424(11) Uani 1 1 d . . . . .
C1S C 0.8761(7) -0.0815(5) 0.9644(3) 0.0307(12) Uani 1 1 d . . . . .
C2S C 1.0062(8) -0.0928(7) 0.8918(4) 0.0456(16) Uani 1 1 d . . . . .
H2SA H 0.9741 -0.1558 0.8641 0.068 Uiso 1 1 calc R U . . .
H2SB H 1.1184 -0.1269 0.9046 0.068 Uiso 1 1 calc R U . . .
H2SC H 1.0110 -0.0032 0.8593 0.068 Uiso 1 1 calc R U . . .
C3S C 0.8630(10) -0.2057(7) 1.0245(4) 0.0515(18) Uani 1 1 d . . . . .
H3SA H 0.7810 -0.1838 1.0704 0.077 Uiso 1 1 calc R U . . .
H3SB H 0.9751 -0.2383 1.0378 0.077 Uiso 1 1 calc R U . . .
H3SC H 0.8243 -0.2765 1.0048 0.077 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 2.112(4) . ?
Co1 N2 2.165(4) . ?
Co1 N4 2.165(4) . ?
Co1 N5 2.139(4) . ?
Co1 N7 2.135(4) . ?
Co1 N8 2.153(4) . ?
O1 N1 1.377(5) . ?
O1 B1 1.503(6) . ?
O2 N4 1.375(5) . ?
O2 B1 1.478(6) . ?
O3 N7 1.369(5) . ?
O3 B1 1.505(6) . ?
N1 C1 1.298(6) . ?
N2 N3 1.351(5) . ?
N2 C2 1.349(6) . ?
N3 H3 0.8278 . ?
N3 C4 1.346(6) . ?
N4 C6 1.283(6) . ?
N5 N6 1.351(6) . ?
N5 C7 1.347(6) . ?
N6 H6 0.9557 . ?
N6 C9 1.348(7) . ?
N7 C11 1.294(6) . ?
N8 N9 1.345(5) . ?
N8 C12 1.341(6) . ?
N9 H9 0.9120 . ?
N9 C14 1.339(6) . ?
C1 C2 1.458(7) . ?
C1 C5 1.492(7) . ?
C2 C3 1.403(7) . ?
C3 H3A 0.9500 . ?
C3 C4 1.375(7) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.463(7) . ?
C6 C10 1.495(7) . ?
C7 C8 1.406(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(8) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.466(7) . ?
C11 C15 1.481(7) . ?
C12 C13 1.413(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(7) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.418(7) . ?
C16 C21 1.397(7) . ?
C16 B1 1.603(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.397(7) . ?
C21 H21 0.9500 . ?
O1S C1S 1.217(6) . ?
C1S C2S 1.502(9) . ?
C1S C3S 1.492(8) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 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
N1 Co1 N2 74.30(15) . . ?
N1 Co1 N4 79.66(15) . . ?
N1 Co1 N5 130.45(16) . . ?
N1 Co1 N7 82.31(15) . . ?
N1 Co1 N8 131.91(16) . . ?
N2 Co1 N4 128.58(15) . . ?
N5 Co1 N2 90.80(16) . . ?
N5 Co1 N4 73.71(15) . . ?
N5 Co1 N8 95.40(15) . . ?
N7 Co1 N2 136.65(16) . . ?
N7 Co1 N4 80.45(15) . . ?
N7 Co1 N5 131.39(16) . . ?
N7 Co1 N8 74.95(15) . . ?
N8 Co1 N2 94.22(15) . . ?
N8 Co1 N4 135.03(15) . . ?
N1 O1 B1 114.8(3) . . ?
N4 O2 B1 114.2(3) . . ?
N7 O3 B1 114.2(4) . . ?
O1 N1 Co1 124.2(3) . . ?
C1 N1 Co1 121.0(3) . . ?
C1 N1 O1 114.7(4) . . ?
N3 N2 Co1 140.4(3) . . ?
C2 N2 Co1 114.3(3) . . ?
C2 N2 N3 104.8(4) . . ?
N2 N3 H3 122.6 . . ?
C4 N3 N2 112.2(4) . . ?
C4 N3 H3 125.1 . . ?
O2 N4 Co1 124.0(3) . . ?
C6 N4 Co1 119.8(3) . . ?
C6 N4 O2 116.1(4) . . ?
N6 N5 Co1 138.5(3) . . ?
C7 N5 Co1 116.1(3) . . ?
C7 N5 N6 105.4(4) . . ?
N5 N6 H6 126.8 . . ?
C9 N6 N5 111.4(4) . . ?
C9 N6 H6 121.6 . . ?
O3 N7 Co1 124.6(3) . . ?
C11 N7 Co1 119.7(3) . . ?
C11 N7 O3 115.6(4) . . ?
N9 N8 Co1 140.7(3) . . ?
C12 N8 Co1 113.6(3) . . ?
C12 N8 N9 105.6(4) . . ?
N8 N9 H9 122.9 . . ?
C14 N9 N8 111.9(4) . . ?
C14 N9 H9 125.1 . . ?
N1 C1 C2 112.7(4) . . ?
N1 C1 C5 124.7(5) . . ?
C2 C1 C5 122.5(4) . . ?
N2 C2 C1 117.5(4) . . ?
N2 C2 C3 110.6(4) . . ?
C3 C2 C1 131.8(4) . . ?
C2 C3 H3A 127.4 . . ?
C4 C3 C2 105.2(4) . . ?
C4 C3 H3A 127.4 . . ?
N3 C4 C3 107.1(5) . . ?
N3 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 113.2(4) . . ?
N4 C6 C10 125.7(5) . . ?
C7 C6 C10 121.0(4) . . ?
N5 C7 C6 117.0(4) . . ?
N5 C7 C8 110.8(4) . . ?
C8 C7 C6 132.2(5) . . ?
C7 C8 H8 127.8 . . ?
C9 C8 C7 104.5(5) . . ?
C9 C8 H8 127.8 . . ?
N6 C9 C8 108.0(5) . . ?
N6 C9 H9A 126.0 . . ?
C8 C9 H9A 126.0 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 112.4(4) . . ?
N7 C11 C15 125.1(5) . . ?
C12 C11 C15 122.4(4) . . ?
N8 C12 C11 118.9(4) . . ?
N8 C12 C13 110.7(4) . . ?
C13 C12 C11 130.3(4) . . ?
C12 C13 H13 128.0 . . ?
C14 C13 C12 104.0(4) . . ?
C14 C13 H13 128.0 . . ?
N9 C14 C13 107.8(4) . . ?
N9 C14 H14 126.1 . . ?
C13 C14 H14 126.1 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 B1 120.0(4) . . ?
C21 C16 C17 116.6(4) . . ?
C21 C16 B1 123.4(4) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(5) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(5) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.6(5) . . ?
C20 C21 H21 119.2 . . ?
O1 B1 O3 111.4(4) . . ?
O1 B1 C16 106.0(4) . . ?
O2 B1 O1 111.9(4) . . ?
O2 B1 O3 111.4(4) . . ?
O2 B1 C16 109.6(4) . . ?
O3 B1 C16 106.1(4) . . ?
O1S C1S C2S 120.6(6) . . ?
O1S C1S C3S 122.4(6) . . ?
C3S C1S C2S 117.1(5) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C3S H3SA 109.5 . . ?
C1S C3S H3SB 109.5 . . ?
C1S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 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 C1 C2 -0.9(6) . . . . ?
Co1 N1 C1 C5 -178.8(4) . . . . ?
Co1 N2 N3 C4 -171.8(4) . . . . ?
Co1 N2 C2 C1 -3.4(5) . . . . ?
Co1 N2 C2 C3 174.3(3) . . . . ?
Co1 N4 C6 C7 3.0(5) . . . . ?
Co1 N4 C6 C10 -176.7(4) . . . . ?
Co1 N5 N6 C9 -178.7(4) . . . . ?
Co1 N5 C7 C6 -1.2(5) . . . . ?
Co1 N5 C7 C8 178.9(3) . . . . ?
Co1 N7 C11 C12 -6.0(5) . . . . ?
Co1 N7 C11 C15 175.6(4) . . . . ?
Co1 N8 N9 C14 -179.3(4) . . . . ?
Co1 N8 C12 C11 2.3(6) . . . . ?
Co1 N8 C12 C13 -179.9(3) . . . . ?
O1 N1 C1 C2 179.5(4) . . . . ?
O1 N1 C1 C5 1.5(7) . . . . ?
O2 N4 C6 C7 -179.4(4) . . . . ?
O2 N4 C6 C10 1.0(7) . . . . ?
O3 N7 C11 C12 177.7(4) . . . . ?
O3 N7 C11 C15 -0.7(7) . . . . ?
N1 O1 B1 O2 59.4(5) . . . . ?
N1 O1 B1 O3 -66.1(5) . . . . ?
N1 O1 B1 C16 178.9(4) . . . . ?
N1 C1 C2 N2 2.9(6) . . . . ?
N1 C1 C2 C3 -174.3(5) . . . . ?
N2 N3 C4 C3 0.4(6) . . . . ?
N2 C2 C3 C4 -0.2(6) . . . . ?
N3 N2 C2 C1 -177.4(4) . . . . ?
N3 N2 C2 C3 0.4(5) . . . . ?
N4 O2 B1 O1 -62.8(5) . . . . ?
N4 O2 B1 O3 62.6(5) . . . . ?
N4 O2 B1 C16 179.8(3) . . . . ?
N4 C6 C7 N5 -1.1(6) . . . . ?
N4 C6 C7 C8 178.7(5) . . . . ?
N5 N6 C9 C8 -0.9(6) . . . . ?
N5 C7 C8 C9 0.6(6) . . . . ?
N6 N5 C7 C6 178.8(4) . . . . ?
N6 N5 C7 C8 -1.1(6) . . . . ?
N7 O3 B1 O1 60.4(5) . . . . ?
N7 O3 B1 O2 -65.3(5) . . . . ?
N7 O3 B1 C16 175.4(3) . . . . ?
N7 C11 C12 N8 2.2(6) . . . . ?
N7 C11 C12 C13 -175.1(5) . . . . ?
N8 N9 C14 C13 0.2(6) . . . . ?
N8 C12 C13 C14 -1.0(6) . . . . ?
N9 N8 C12 C11 -176.6(4) . . . . ?
N9 N8 C12 C13 1.2(5) . . . . ?
C1 C2 C3 C4 177.2(5) . . . . ?
C2 N2 N3 C4 -0.5(5) . . . . ?
C2 C3 C4 N3 -0.1(6) . . . . ?
C5 C1 C2 N2 -179.1(5) . . . . ?
C5 C1 C2 C3 3.7(9) . . . . ?
C6 C7 C8 C9 -179.3(5) . . . . ?
C7 N5 N6 C9 1.2(6) . . . . ?
C7 C8 C9 N6 0.2(6) . . . . ?
C10 C6 C7 N5 178.6(4) . . . . ?
C10 C6 C7 C8 -1.6(8) . . . . ?
C11 C12 C13 C14 176.4(5) . . . . ?
C12 N8 N9 C14 -0.9(5) . . . . ?
C12 C13 C14 N9 0.5(6) . . . . ?
C15 C11 C12 N8 -179.3(5) . . . . ?
C15 C11 C12 C13 3.5(8) . . . . ?
C16 C17 C18 C19 0.5(8) . . . . ?
C17 C16 C21 C20 1.4(7) . . . . ?
C17 C16 B1 O1 49.3(6) . . . . ?
C17 C16 B1 O2 170.3(4) . . . . ?
C17 C16 B1 O3 -69.2(5) . . . . ?
C17 C18 C19 C20 0.0(8) . . . . ?
C18 C19 C20 C21 0.3(8) . . . . ?
C19 C20 C21 C16 -1.0(8) . . . . ?
C21 C16 C17 C18 -1.2(7) . . . . ?
C21 C16 B1 O1 -131.4(5) . . . . ?
C21 C16 B1 O2 -10.4(6) . . . . ?
C21 C16 B1 O3 110.1(5) . . . . ?
B1 O1 N1 Co1 6.9(5) . . . . ?
B1 O1 N1 C1 -173.5(4) . . . . ?
B1 O2 N4 Co1 1.2(5) . . . . ?
B1 O2 N4 C6 -176.3(4) . . . . ?
B1 O3 N7 Co1 2.3(5) . . . . ?
B1 O3 N7 C11 178.4(4) . . . . ?
B1 C16 C17 C18 178.2(5) . . . . ?
B1 C16 C21 C20 -177.9(4) . . . . ?

_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_AB366
_database_code_depnum_ccdc_archive 'CCDC 2286594'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-07-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 B Co N9 O3, Cl, C H Cl3'
_chemical_formula_sum            'C22 H24 B Cl4 Co N9 O3'
_chemical_formula_weight         674.04
_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 0.0070 0.0030 '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'
B B 0.0030 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.2283 0.2894 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.2560 1.6600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0125 0.0065 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0220 0.0120 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3209(17)
_cell_length_b                   19.369(4)
_cell_length_c                   18.121(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.84(3)
_cell_angle_gamma                90
_cell_volume                     2905.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2305
_cell_measurement_temperature    100
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    2.387
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1372
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1508
_diffrn_reflns_av_unetI/netI     0.2182
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15044
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        35.279
_diffrn_reflns_theta_max         38.568
_diffrn_reflns_theta_min         3.061
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.9626
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3669
_reflns_number_total             6162
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      0.950
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1S(H1S)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N9(H9), C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_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 0.44137(6) 0.36748(2) 0.28723(3) 0.0276(2) Uani 1 1 d . . . . .
O1 O 0.5468(3) 0.36917(11) 0.45964(15) 0.0337(6) Uani 1 1 d . . . . .
O2 O 0.2836(3) 0.30959(10) 0.42399(14) 0.0318(6) Uani 1 1 d . . . . .
O3 O 0.2984(3) 0.43756(10) 0.42316(14) 0.0307(6) Uani 1 1 d . . . . .
N1 N 0.5997(4) 0.36911(12) 0.38979(18) 0.0284(7) Uani 1 1 d . . . . .
N2 N 0.6823(4) 0.36625(13) 0.25409(19) 0.0328(8) Uani 1 1 d . . . . .
N3 N 0.7575(4) 0.36948(13) 0.19111(19) 0.0326(8) Uani 1 1 d . . . . .
H3 H 0.7079 0.3654 0.1461 0.039 Uiso 1 1 calc R U . . .
N4 N 0.2980(4) 0.30164(13) 0.34930(17) 0.0294(7) Uani 1 1 d . . . . .
N5 N 0.3314(4) 0.29237(13) 0.20798(17) 0.0303(7) Uani 1 1 d . . . . .
N6 N 0.3138(4) 0.28080(13) 0.13370(17) 0.0327(8) Uani 1 1 d . . . . .
H6 H 0.3715 0.3015 0.1021 0.039 Uiso 1 1 calc R U . . .
N7 N 0.3236(4) 0.44412(13) 0.34886(18) 0.0287(7) Uani 1 1 d . . . . .
N8 N 0.3726(4) 0.45114(13) 0.20956(18) 0.0316(8) Uani 1 1 d . . . . .
N9 N 0.3831(4) 0.46874(14) 0.13795(19) 0.0394(8) Uani 1 1 d . . . . .
H9 H 0.4316 0.4432 0.1067 0.047 Uiso 1 1 calc R U . . .
C1 C 0.7538(5) 0.37566(15) 0.3865(2) 0.0290(9) Uani 1 1 d . . . . .
C2 C 0.7993(5) 0.37527(15) 0.3105(2) 0.0285(9) Uani 1 1 d . . . . .
C3 C 0.9501(5) 0.38376(18) 0.2828(2) 0.0346(10) Uani 1 1 d . . . . .
H3A H 1.0521 0.3908 0.3104 0.042 Uiso 1 1 calc R U . . .
C4 C 0.9174(5) 0.37969(17) 0.2062(2) 0.0399(11) Uani 1 1 d . . . . .
H4 H 0.9939 0.3834 0.1709 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8769(5) 0.3853(2) 0.4529(3) 0.0464(11) Uani 1 1 d . . . . .
H5A H 0.8592 0.4300 0.4762 0.070 Uiso 1 1 calc R U . . .
H5B H 0.9858 0.3841 0.4369 0.070 Uiso 1 1 calc R U . . .
H5C H 0.8655 0.3482 0.4887 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2042(4) 0.25544(16) 0.3153(2) 0.0285(8) Uani 1 1 d . . . . .
C7 C 0.2194(4) 0.25072(16) 0.2357(2) 0.0302(9) Uani 1 1 d . . . . .
C8 C 0.1334(5) 0.21328(16) 0.1781(2) 0.0339(10) Uani 1 1 d . . . . .
H8 H 0.0494 0.1808 0.1824 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1963(5) 0.23356(17) 0.1138(2) 0.0359(9) Uani 1 1 d . . . . .
H9A H 0.1638 0.2175 0.0650 0.043 Uiso 1 1 calc R U . . .
C10 C 0.0819(5) 0.21495(17) 0.3530(2) 0.0396(10) Uani 1 1 d . . . . .
H10A H 0.1360 0.1911 0.3963 0.059 Uiso 1 1 calc R U . . .
H10B H 0.0300 0.1810 0.3182 0.059 Uiso 1 1 calc R U . . .
H10C H 0.0000 0.2464 0.3689 0.059 Uiso 1 1 calc R U . . .
C11 C 0.2617(4) 0.49969(17) 0.3163(2) 0.0303(9) Uani 1 1 d . . . . .
C12 C 0.2891(5) 0.50389(17) 0.2378(2) 0.0322(9) Uani 1 1 d . . . . .
C13 C 0.2476(5) 0.55355(18) 0.1829(2) 0.0388(10) Uani 1 1 d . . . . .
H13 H 0.1882 0.5949 0.1880 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3110(5) 0.52989(18) 0.1197(2) 0.0428(10) Uani 1 1 d . . . . .
H14 H 0.3049 0.5522 0.0728 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1696(5) 0.55291(17) 0.3550(2) 0.0416(10) Uani 1 1 d . . . . .
H15A H 0.0785 0.5308 0.3760 0.062 Uiso 1 1 calc R U . . .
H15B H 0.1290 0.5885 0.3194 0.062 Uiso 1 1 calc R U . . .
H15C H 0.2411 0.5742 0.3949 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3237(4) 0.37517(16) 0.5445(2) 0.0272(9) Uani 1 1 d . . . . .
C17 C 0.3667(4) 0.43417(16) 0.5895(2) 0.0316(9) Uani 1 1 d . . . . .
H17 H 0.4227 0.4712 0.5691 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3290(5) 0.43906(17) 0.6622(2) 0.0347(9) Uani 1 1 d . . . . .
H18 H 0.3594 0.4791 0.6905 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2472(5) 0.38590(18) 0.6941(2) 0.0384(10) Uani 1 1 d . . . . .
H19 H 0.2212 0.3893 0.7438 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2041(5) 0.32715(18) 0.6514(2) 0.0373(10) Uani 1 1 d . . . . .
H20 H 0.1480 0.2905 0.6724 0.045 Uiso 1 1 calc R U . . .
C21 C 0.2423(4) 0.32189(17) 0.5789(2) 0.0340(9) Uani 1 1 d . . . . .
H21 H 0.2129 0.2812 0.5514 0.041 Uiso 1 1 calc R U . . .
B1 B 0.3660(6) 0.37185(18) 0.4597(2) 0.0283(10) Uani 1 1 d . . . . .
Cl1 Cl 0.55025(13) 0.36282(4) 0.03651(5) 0.0396(3) Uani 1 1 d . . . . .
Cl1S Cl 0.0132(2) 0.38920(9) 0.00101(9) 0.1102(7) Uani 1 1 d . . . . .
Cl2S Cl 0.19299(17) 0.45901(5) -0.10688(9) 0.0701(4) Uani 1 1 d . . . . .
Cl3S Cl 0.11894(15) 0.31264(5) -0.12252(8) 0.0657(4) Uani 1 1 d . . . . .
C1S C 0.1666(6) 0.3804(2) -0.0592(3) 0.0592(13) Uani 1 1 d . . . . .
H1S H 0.2702 0.3689 -0.0288 0.071 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 2.166(3) . ?
Co1 N2 2.151(3) . ?
Co1 N4 2.142(3) . ?
Co1 N5 2.179(3) . ?
Co1 N7 2.153(3) . ?
Co1 N8 2.184(3) . ?
O1 N1 1.382(4) . ?
O1 B1 1.506(5) . ?
O2 N4 1.379(4) . ?
O2 B1 1.501(5) . ?
O3 N7 1.389(4) . ?
O3 B1 1.516(4) . ?
N1 C1 1.296(5) . ?
N2 N3 1.358(4) . ?
N2 C2 1.349(5) . ?
N3 H3 0.8800 . ?
N3 C4 1.345(5) . ?
N4 C6 1.301(4) . ?
N5 N6 1.358(4) . ?
N5 C7 1.366(4) . ?
N6 H6 0.8800 . ?
N6 C9 1.360(5) . ?
N7 C11 1.307(4) . ?
N8 N9 1.353(4) . ?
N8 C12 1.364(4) . ?
N9 H9 0.8800 . ?
N9 C14 1.354(5) . ?
C1 C2 1.466(5) . ?
C1 C5 1.510(6) . ?
C2 C3 1.408(5) . ?
C3 H3A 0.9500 . ?
C3 C4 1.389(6) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.464(5) . ?
C6 C10 1.503(5) . ?
C7 C8 1.405(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(5) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.465(5) . ?
C11 C15 1.500(5) . ?
C12 C13 1.402(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.429(5) . ?
C16 C21 1.413(5) . ?
C16 B1 1.612(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.403(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(5) . ?
C21 H21 0.9500 . ?
Cl1S C1S 1.769(5) . ?
Cl2S C1S 1.775(5) . ?
Cl3S C1S 1.762(5) . ?
C1S H1S 1.0000 . ?

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 N5 138.86(10) . . ?
N1 Co1 N8 129.69(10) . . ?
N2 Co1 N1 74.75(13) . . ?
N2 Co1 N5 98.59(12) . . ?
N2 Co1 N7 129.72(11) . . ?
N2 Co1 N8 91.08(11) . . ?
N4 Co1 N1 83.15(12) . . ?
N4 Co1 N2 136.46(11) . . ?
N4 Co1 N5 74.32(11) . . ?
N4 Co1 N7 80.25(11) . . ?
N4 Co1 N8 131.04(11) . . ?
N5 Co1 N8 90.33(11) . . ?
N7 Co1 N1 79.28(11) . . ?
N7 Co1 N5 128.27(12) . . ?
N7 Co1 N8 73.70(11) . . ?
N1 O1 B1 114.3(3) . . ?
N4 O2 B1 115.5(2) . . ?
N7 O3 B1 114.5(2) . . ?
O1 N1 Co1 124.3(2) . . ?
C1 N1 Co1 118.7(3) . . ?
C1 N1 O1 116.8(3) . . ?
N3 N2 Co1 139.2(3) . . ?
C2 N2 Co1 114.1(3) . . ?
C2 N2 N3 105.8(3) . . ?
N2 N3 H3 124.3 . . ?
C4 N3 N2 111.5(3) . . ?
C4 N3 H3 124.3 . . ?
O2 N4 Co1 123.88(19) . . ?
C6 N4 Co1 120.0(2) . . ?
C6 N4 O2 115.7(3) . . ?
N6 N5 Co1 139.4(2) . . ?
N6 N5 C7 104.9(3) . . ?
C7 N5 Co1 114.1(2) . . ?
N5 N6 H6 124.0 . . ?
N5 N6 C9 112.1(3) . . ?
C9 N6 H6 124.0 . . ?
O3 N7 Co1 124.14(18) . . ?
C11 N7 Co1 120.9(3) . . ?
C11 N7 O3 114.9(3) . . ?
N9 N8 Co1 140.1(2) . . ?
N9 N8 C12 104.9(3) . . ?
C12 N8 Co1 115.1(2) . . ?
N8 N9 H9 123.7 . . ?
N8 N9 C14 112.6(3) . . ?
C14 N9 H9 123.7 . . ?
N1 C1 C2 113.2(3) . . ?
N1 C1 C5 124.7(4) . . ?
C2 C1 C5 122.1(4) . . ?
N2 C2 C1 118.5(3) . . ?
N2 C2 C3 110.3(4) . . ?
C3 C2 C1 131.2(4) . . ?
C2 C3 H3A 127.5 . . ?
C4 C3 C2 104.9(4) . . ?
C4 C3 H3A 127.5 . . ?
N3 C4 C3 107.5(3) . . ?
N3 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 113.7(3) . . ?
N4 C6 C10 123.0(3) . . ?
C7 C6 C10 123.1(3) . . ?
N5 C7 C6 117.1(3) . . ?
N5 C7 C8 110.3(3) . . ?
C8 C7 C6 132.5(3) . . ?
C7 C8 H8 127.1 . . ?
C9 C8 C7 105.7(3) . . ?
C9 C8 H8 127.1 . . ?
N6 C9 C8 107.0(3) . . ?
N6 C9 H9A 126.5 . . ?
C8 C9 H9A 126.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 113.0(3) . . ?
N7 C11 C15 123.5(3) . . ?
C12 C11 C15 123.6(3) . . ?
N8 C12 C11 117.3(3) . . ?
N8 C12 C13 110.2(3) . . ?
C13 C12 C11 132.5(3) . . ?
C12 C13 H13 127.1 . . ?
C14 C13 C12 105.8(3) . . ?
C14 C13 H13 127.1 . . ?
N9 C14 C13 106.5(4) . . ?
N9 C14 H14 126.7 . . ?
C13 C14 H14 126.7 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 B1 120.7(3) . . ?
C21 C16 C17 115.8(3) . . ?
C21 C16 B1 123.5(3) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.6(4) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 119.0 . . ?
C20 C21 C16 122.0(3) . . ?
C20 C21 H21 119.0 . . ?
O1 B1 O3 110.8(3) . . ?
O1 B1 C16 108.5(3) . . ?
O2 B1 O1 112.6(3) . . ?
O2 B1 O3 110.7(3) . . ?
O2 B1 C16 108.0(3) . . ?
O3 B1 C16 106.0(3) . . ?
Cl1S C1S Cl2S 110.5(2) . . ?
Cl1S C1S H1S 108.5 . . ?
Cl2S C1S H1S 108.5 . . ?
Cl3S C1S Cl1S 110.2(3) . . ?
Cl3S C1S Cl2S 110.6(3) . . ?
Cl3S C1S H1S 108.5 . . ?

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 C1 C2 -4.9(3) . . . . ?
Co1 N1 C1 C5 173.1(3) . . . . ?
Co1 N2 N3 C4 167.9(2) . . . . ?
Co1 N2 C2 C1 7.8(3) . . . . ?
Co1 N2 C2 C3 -171.5(2) . . . . ?
Co1 N4 C6 C7 4.8(4) . . . . ?
Co1 N4 C6 C10 -170.4(3) . . . . ?
Co1 N5 N6 C9 -164.3(3) . . . . ?
Co1 N5 C7 C6 -7.9(4) . . . . ?
Co1 N5 C7 C8 168.9(2) . . . . ?
Co1 N7 C11 C12 -2.7(4) . . . . ?
Co1 N7 C11 C15 176.2(3) . . . . ?
Co1 N8 N9 C14 178.6(3) . . . . ?
Co1 N8 C12 C11 2.4(4) . . . . ?
Co1 N8 C12 C13 -178.4(3) . . . . ?
O1 N1 C1 C2 -179.8(2) . . . . ?
O1 N1 C1 C5 -1.9(4) . . . . ?
O2 N4 C6 C7 177.8(3) . . . . ?
O2 N4 C6 C10 2.7(5) . . . . ?
O3 N7 C11 C12 -179.1(3) . . . . ?
O3 N7 C11 C15 -0.2(5) . . . . ?
N1 O1 B1 O2 63.1(3) . . . . ?
N1 O1 B1 O3 -61.5(3) . . . . ?
N1 O1 B1 C16 -177.4(2) . . . . ?
N1 C1 C2 N2 -2.1(4) . . . . ?
N1 C1 C2 C3 177.0(3) . . . . ?
N2 N3 C4 C3 -0.3(4) . . . . ?
N2 C2 C3 C4 0.3(4) . . . . ?
N3 N2 C2 C1 178.8(3) . . . . ?
N3 N2 C2 C3 -0.4(3) . . . . ?
N4 O2 B1 O1 -64.6(4) . . . . ?
N4 O2 B1 O3 60.0(4) . . . . ?
N4 O2 B1 C16 175.6(3) . . . . ?
N4 C6 C7 N5 2.3(5) . . . . ?
N4 C6 C7 C8 -173.6(4) . . . . ?
N5 N6 C9 C8 0.2(4) . . . . ?
N5 C7 C8 C9 -0.1(4) . . . . ?
N6 N5 C7 C6 -176.5(3) . . . . ?
N6 N5 C7 C8 0.3(4) . . . . ?
N7 O3 B1 O1 62.4(4) . . . . ?
N7 O3 B1 O2 -63.3(4) . . . . ?
N7 O3 B1 C16 179.9(3) . . . . ?
N7 C11 C12 N8 0.1(5) . . . . ?
N7 C11 C12 C13 -178.9(4) . . . . ?
N8 N9 C14 C13 -0.7(4) . . . . ?
N8 C12 C13 C14 -0.9(4) . . . . ?
N9 N8 C12 C11 -178.7(3) . . . . ?
N9 N8 C12 C13 0.5(4) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C2 N2 N3 C4 0.4(3) . . . . ?
C2 C3 C4 N3 0.0(4) . . . . ?
C5 C1 C2 N2 179.9(3) . . . . ?
C5 C1 C2 C3 -1.0(5) . . . . ?
C6 C7 C8 C9 176.0(4) . . . . ?
C7 N5 N6 C9 -0.3(4) . . . . ?
C7 C8 C9 N6 -0.1(4) . . . . ?
C10 C6 C7 N5 177.5(3) . . . . ?
C10 C6 C7 C8 1.6(6) . . . . ?
C11 C12 C13 C14 178.2(4) . . . . ?
C12 N8 N9 C14 0.1(4) . . . . ?
C12 C13 C14 N9 0.9(4) . . . . ?
C15 C11 C12 N8 -178.8(3) . . . . ?
C15 C11 C12 C13 2.1(6) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C16 C21 C20 1.1(5) . . . . ?
C17 C16 B1 O1 66.4(4) . . . . ?
C17 C16 B1 O2 -171.2(3) . . . . ?
C17 C16 B1 O3 -52.6(4) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C16 -0.9(6) . . . . ?
C21 C16 C17 C18 -0.7(5) . . . . ?
C21 C16 B1 O1 -114.2(4) . . . . ?
C21 C16 B1 O2 8.2(5) . . . . ?
C21 C16 B1 O3 126.8(3) . . . . ?
B1 O1 N1 Co1 -3.1(3) . . . . ?
B1 O1 N1 C1 171.5(3) . . . . ?
B1 O2 N4 Co1 4.6(4) . . . . ?
B1 O2 N4 C6 -168.2(3) . . . . ?
B1 O3 N7 Co1 1.9(4) . . . . ?
B1 O3 N7 C11 178.2(3) . . . . ?
B1 C16 C17 C18 178.7(3) . . . . ?
B1 C16 C21 C20 -178.3(3) . . . . ?

_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_sv127_co
_database_code_depnum_ccdc_archive 'CCDC 2286464'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-07-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C21 H23 B Co N9 O3, C4 H8 O'
_chemical_formula_sum            'C25 H31 B Br Co N9 O4'
_chemical_formula_weight         671.24
_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'
B B 0.0013 0.0007 '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                   8.1745(16)
_cell_length_b                   13.088(3)
_cell_length_c                   14.139(3)
_cell_angle_alpha                89.31(3)
_cell_angle_beta                 75.61(3)
_cell_angle_gamma                78.60(3)
_cell_volume                     1435.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.750
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_correction_T_min  0.3655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0943 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8441.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             686
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1239
_diffrn_reflns_av_unetI/netI     0.1468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20076
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.488
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3436
_reflns_number_total             6260
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6260
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      0.949
_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)+(0.0458P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S \\sim O1S'-C1S'
 with sigma of 0.02
 O1S'-C4S' \\sim O1S-C4S
 with sigma of 0.02
 C1S'-C2S' \\sim C2S-C1S
 with sigma of 0.02
 C2S-C3S \\sim C2S'-C3S'
 with sigma of 0.02
 C4S'-C3S' \\sim C4S-C3S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2S') \\sim Ueq, Uanis(C2S) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C1S') \\sim Ueq, Uanis(C1S) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1S') \\sim Ueq, Uanis(O1S) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1S) = Uanis(O1S')
Uanis(C1S') = Uanis(C1S)
Uanis(C2S') = Uanis(C2S)
Uanis(C3S') = Uanis(C3S)
Uanis(C4S') = Uanis(C4S)
4. Others
 Sof(O1S')=Sof(C1S')=Sof(H1SC)=Sof(H1SD)=Sof(C2S')=Sof(H2SC)=Sof(H2SD)=
 Sof(C3S')=Sof(H3SC)=Sof(H3SD)=Sof(C4S')=Sof(H4SC)=Sof(H4SD)=1-FVAR(1)
 Sof(O1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(C3S)=
 Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=FVAR(1)
5.a Everything fixed:
 H3, H6, H9
5.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB), C1S'(H1SC,
 H1SD), C2S'(H2SC,H2SD), C3S'(H3SC,H3SD), C4S'(H4SC,H4SD)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.30451(8) 1.42069(5) 0.53598(5) 0.03114(19) Uani 1 1 d . . . . .
Co1 Co 0.50297(8) 1.12470(5) 0.30487(5) 0.01290(18) Uani 1 1 d . . . . .
O1 O 0.6976(4) 0.8950(3) 0.2439(2) 0.0193(8) Uani 1 1 d . . . . .
O2 O 0.4374(4) 0.9511(3) 0.1792(2) 0.0165(8) Uani 1 1 d . . . . .
O3 O 0.7063(4) 1.0100(2) 0.1036(2) 0.0156(8) Uani 1 1 d . . . . .
N1 N 0.6634(5) 1.1029(3) 0.1580(3) 0.0147(9) Uani 1 1 d . . . . .
N2 N 0.5796(5) 1.2721(3) 0.2672(3) 0.0157(9) Uani 1 1 d . . . . .
N3 N 0.5680(5) 1.3673(3) 0.3090(3) 0.0178(10) Uani 1 1 d . . . . .
H3 H 0.5043 1.3806 0.3767 0.050 Uiso 1 1 d . . . . .
N4 N 0.3639(5) 1.0393(3) 0.2384(3) 0.0143(9) Uani 1 1 d . . . . .
N5 N 0.2374(5) 1.2065(3) 0.3489(3) 0.0164(10) Uani 1 1 d . . . . .
N6 N 0.1396(5) 1.2937(3) 0.4008(3) 0.0169(10) Uani 1 1 d . . . . .
H6 H 0.1958 1.3339 0.4390 0.050 Uiso 1 1 d . . . . .
N7 N 0.6603(5) 0.9750(3) 0.3134(3) 0.0140(9) Uani 1 1 d . . . . .
N8 N 0.5795(5) 1.1272(3) 0.4405(3) 0.0179(10) Uani 1 1 d . . . . .
N9 N 0.5676(5) 1.1943(3) 0.5152(3) 0.0189(10) Uani 1 1 d . . . . .
H9 H 0.4996 1.2577 0.5170 0.050 Uiso 1 1 d . . . . .
C1 C 0.7277(6) 1.1786(4) 0.1151(4) 0.0161(11) Uani 1 1 d . . . . .
C2 C 0.6821(6) 1.2736(4) 0.1767(4) 0.0171(11) Uani 1 1 d . . . . .
C3 C 0.7340(7) 1.3698(4) 0.1619(4) 0.0285(14) Uani 1 1 d . . . . .
H3A H 0.8059 1.3911 0.1046 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6590(7) 1.4263(4) 0.2477(4) 0.0273(14) Uani 1 1 d . . . . .
H4 H 0.6696 1.4952 0.2614 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8407(7) 1.1710(4) 0.0127(4) 0.0255(13) Uani 1 1 d . . . . .
H5A H 0.9333 1.1091 0.0050 0.038 Uiso 1 1 calc R U . . .
H5B H 0.8909 1.2335 0.0002 0.038 Uiso 1 1 calc R U . . .
H5C H 0.7716 1.1656 -0.0339 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2003(6) 1.0724(4) 0.2478(3) 0.0146(11) Uani 1 1 d . . . . .
C7 C 0.1275(6) 1.1662(4) 0.3112(3) 0.0135(11) Uani 1 1 d . . . . .
C8 C -0.0402(6) 1.2280(4) 0.3403(4) 0.0212(12) Uani 1 1 d . . . . .
H8 H -0.1411 1.2164 0.3239 0.025 Uiso 1 1 calc R U . . .
C9 C -0.0265(6) 1.3084(4) 0.3974(4) 0.0222(13) Uani 1 1 d . . . . .
H9A H -0.1171 1.3639 0.4285 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0941(6) 1.0227(4) 0.1983(4) 0.0234(13) Uani 1 1 d . . . . .
H10A H 0.1128 0.9478 0.2099 0.035 Uiso 1 1 calc R U . . .
H10B H 0.1274 1.0333 0.1280 0.035 Uiso 1 1 calc R U . . .
H10C H -0.0280 1.0542 0.2245 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7362(6) 0.9529(4) 0.3833(4) 0.0162(11) Uani 1 1 d . . . . .
C12 C 0.6939(6) 1.0407(4) 0.4531(3) 0.0137(11) Uani 1 1 d . . . . .
C13 C 0.7513(6) 1.0534(4) 0.5360(3) 0.0194(12) Uani 1 1 d . . . . .
H13 H 0.8306 1.0049 0.5614 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6676(7) 1.1522(4) 0.5732(4) 0.0253(13) Uani 1 1 d . . . . .
H14 H 0.6791 1.1848 0.6302 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8566(6) 0.8527(4) 0.3894(4) 0.0210(12) Uani 1 1 d . . . . .
H15A H 0.9547 0.8427 0.3318 0.031 Uiso 1 1 calc R U . . .
H15B H 0.7961 0.7948 0.3920 0.031 Uiso 1 1 calc R U . . .
H15C H 0.8983 0.8548 0.4485 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6920(6) 0.8214(4) 0.0847(4) 0.0167(12) Uani 1 1 d . . . . .
C17 C 0.6527(6) 0.8233(4) -0.0053(4) 0.0193(12) Uani 1 1 d . . . . .
H17 H 0.5902 0.8856 -0.0247 0.023 Uiso 1 1 calc R U . . .
C18 C 0.7040(7) 0.7343(4) -0.0677(4) 0.0242(13) Uani 1 1 d . . . . .
H18 H 0.6780 0.7373 -0.1297 0.029 Uiso 1 1 calc R U . . .
C19 C 0.7924(7) 0.6422(4) -0.0401(4) 0.0287(14) Uani 1 1 d . . . . .
H19 H 0.8249 0.5819 -0.0824 0.034 Uiso 1 1 calc R U . . .
C20 C 0.8336(7) 0.6379(4) 0.0497(4) 0.0281(14) Uani 1 1 d . . . . .
H20 H 0.8966 0.5755 0.0688 0.034 Uiso 1 1 calc R U . . .
C21 C 0.7814(7) 0.7261(4) 0.1104(4) 0.0229(13) Uani 1 1 d . . . . .
H21 H 0.8067 0.7224 0.1725 0.028 Uiso 1 1 calc R U . . .
B1 B 0.6314(8) 0.9229(5) 0.1560(4) 0.0183(14) Uani 1 1 d . . . . .
O1S O 0.7673(11) 1.2933(6) -0.2759(5) 0.0499(18) Uani 0.612(7) 1 d D U P A 1
C1S C 0.818(2) 1.3877(12) -0.3198(10) 0.041(3) Uani 0.612(7) 1 d D U P A 1
H1SA H 0.7431 1.4176 -0.3627 0.049 Uiso 0.612(7) 1 calc R U P A 1
H1SB H 0.9391 1.3718 -0.3592 0.049 Uiso 0.612(7) 1 calc R U P A 1
C2S C 0.798(2) 1.4629(12) -0.2355(10) 0.039(3) Uani 0.612(7) 1 d D U P A 1
H2SA H 0.7363 1.5331 -0.2474 0.046 Uiso 0.612(7) 1 calc R U P A 1
H2SB H 0.9120 1.4686 -0.2263 0.046 Uiso 0.612(7) 1 calc R U P A 1
C3S C 0.6943(17) 1.4178(10) -0.1467(10) 0.038(3) Uani 0.612(7) 1 d D . P A 1
H3SA H 0.7668 1.3918 -0.1014 0.045 Uiso 0.612(7) 1 calc R U P A 1
H3SB H 0.5948 1.4712 -0.1113 0.045 Uiso 0.612(7) 1 calc R U P A 1
C4S C 0.6368(18) 1.3338(13) -0.1845(9) 0.037(4) Uani 0.612(7) 1 d D . P A 1
H4SA H 0.5228 1.3592 -0.1981 0.044 Uiso 0.612(7) 1 calc R U P A 1
H4SB H 0.6264 1.2781 -0.1367 0.044 Uiso 0.612(7) 1 calc R U P A 1
O1S' O 0.6507(17) 1.3424(10) -0.2817(9) 0.0499(18) Uani 0.388(7) 1 d D U P A 2
C1S' C 0.784(3) 1.397(2) -0.3287(16) 0.041(3) Uani 0.388(7) 1 d D U P A 2
H1SC H 0.7401 1.4510 -0.3706 0.049 Uiso 0.388(7) 1 calc R U P A 2
H1SD H 0.8834 1.3476 -0.3699 0.049 Uiso 0.388(7) 1 calc R U P A 2
C2S' C 0.839(3) 1.4464(19) -0.2483(15) 0.039(3) Uani 0.388(7) 1 d D U P A 2
H2SC H 0.9656 1.4369 -0.2627 0.046 Uiso 0.388(7) 1 calc R U P A 2
H2SD H 0.7872 1.5218 -0.2394 0.046 Uiso 0.388(7) 1 calc R U P A 2
C3S' C 0.770(3) 1.3888(16) -0.1598(17) 0.038(3) Uani 0.388(7) 1 d D . P A 2
H3SC H 0.8649 1.3571 -0.1302 0.045 Uiso 0.388(7) 1 calc R U P A 2
H3SD H 0.6834 1.4377 -0.1106 0.045 Uiso 0.388(7) 1 calc R U P A 2
C4S' C 0.692(3) 1.309(2) -0.1880(15) 0.037(4) Uani 0.388(7) 1 d D . P A 2
H4SC H 0.5864 1.3034 -0.1377 0.044 Uiso 0.388(7) 1 calc R U P A 2
H4SD H 0.7733 1.2410 -0.1971 0.044 Uiso 0.388(7) 1 calc R U P A 2


_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 2.151(4) . ?
Co1 N2 2.164(4) . ?
Co1 N4 2.118(4) . ?
Co1 N5 2.162(4) . ?
Co1 N7 2.140(4) . ?
Co1 N8 2.162(4) . ?
O1 N7 1.381(5) . ?
O1 B1 1.488(7) . ?
O2 N4 1.376(5) . ?
O2 B1 1.507(7) . ?
O3 N1 1.384(5) . ?
O3 B1 1.501(7) . ?
N1 C1 1.288(6) . ?
N2 N3 1.362(5) . ?
N2 C2 1.347(6) . ?
N3 H3 0.9681 . ?
N3 C4 1.338(6) . ?
N4 C6 1.295(6) . ?
N5 N6 1.359(5) . ?
N5 C7 1.343(6) . ?
N6 H6 1.0026 . ?
N6 C9 1.347(6) . ?
N7 C11 1.294(6) . ?
N8 N9 1.354(5) . ?
N8 C12 1.360(6) . ?
N9 H9 0.8996 . ?
N9 C14 1.338(6) . ?
C1 C2 1.458(7) . ?
C1 C5 1.504(7) . ?
C2 C3 1.403(7) . ?
C3 H3A 0.9500 . ?
C3 C4 1.365(7) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.462(7) . ?
C6 C10 1.485(6) . ?
C7 C8 1.412(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(7) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.454(7) . ?
C11 C15 1.492(6) . ?
C12 C13 1.388(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(7) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.386(7) . ?
C16 C21 1.408(7) . ?
C16 B1 1.597(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(7) . ?
C21 H21 0.9500 . ?
O1S C1S 1.463(12) . ?
O1S C4S 1.482(12) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.512(12) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C3S 1.514(11) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C4S 1.435(11) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
O1S' C1S' 1.441(15) . ?
O1S' C4S' 1.487(17) . ?
C1S' H1SC 0.9900 . ?
C1S' H1SD 0.9900 . ?
C1S' C2S' 1.514(16) . ?
C2S' H2SC 0.9900 . ?
C2S' H2SD 0.9900 . ?
C2S' C3S' 1.498(16) . ?
C3S' H3SC 0.9900 . ?
C3S' H3SD 0.9900 . ?
C3S' C4S' 1.428(16) . ?
C4S' H4SC 0.9900 . ?
C4S' H4SD 0.9900 . ?

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 N2 73.80(15) . . ?
N1 Co1 N5 126.28(15) . . ?
N1 Co1 N8 128.62(15) . . ?
N4 Co1 N1 79.05(15) . . ?
N4 Co1 N2 130.08(15) . . ?
N4 Co1 N5 74.35(15) . . ?
N4 Co1 N7 84.23(15) . . ?
N4 Co1 N8 138.14(16) . . ?
N5 Co1 N2 89.13(15) . . ?
N5 Co1 N8 101.39(15) . . ?
N7 Co1 N1 79.52(15) . . ?
N7 Co1 N2 129.15(15) . . ?
N7 Co1 N5 140.72(16) . . ?
N7 Co1 N8 73.37(15) . . ?
N8 Co1 N2 90.76(15) . . ?
N7 O1 B1 114.7(4) . . ?
N4 O2 B1 115.0(3) . . ?
N1 O3 B1 114.2(4) . . ?
O3 N1 Co1 124.1(3) . . ?
C1 N1 Co1 120.4(3) . . ?
C1 N1 O3 115.5(4) . . ?
N3 N2 Co1 140.0(3) . . ?
C2 N2 Co1 114.9(3) . . ?
C2 N2 N3 104.9(4) . . ?
N2 N3 H3 117.9 . . ?
C4 N3 N2 111.6(4) . . ?
C4 N3 H3 130.4 . . ?
O2 N4 Co1 124.3(3) . . ?
C6 N4 Co1 120.1(3) . . ?
C6 N4 O2 115.5(4) . . ?
N6 N5 Co1 140.1(3) . . ?
C7 N5 Co1 115.0(3) . . ?
C7 N5 N6 104.8(4) . . ?
N5 N6 H6 117.9 . . ?
C9 N6 N5 112.4(4) . . ?
C9 N6 H6 129.5 . . ?
O1 N7 Co1 124.1(3) . . ?
C11 N7 Co1 122.4(3) . . ?
C11 N7 O1 113.4(4) . . ?
N9 N8 Co1 139.9(3) . . ?
N9 N8 C12 105.2(4) . . ?
C12 N8 Co1 114.2(3) . . ?
N8 N9 H9 117.5 . . ?
C14 N9 N8 111.1(4) . . ?
C14 N9 H9 131.4 . . ?
N1 C1 C2 113.1(4) . . ?
N1 C1 C5 124.3(5) . . ?
C2 C1 C5 122.7(5) . . ?
N2 C2 C1 117.8(4) . . ?
N2 C2 C3 110.4(5) . . ?
C3 C2 C1 131.6(5) . . ?
C2 C3 H3A 127.4 . . ?
C4 C3 C2 105.2(5) . . ?
C4 C3 H3A 127.4 . . ?
N3 C4 C3 107.9(5) . . ?
N3 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 113.7(4) . . ?
N4 C6 C10 124.2(5) . . ?
C7 C6 C10 122.0(4) . . ?
N5 C7 C6 116.7(4) . . ?
N5 C7 C8 110.6(4) . . ?
C8 C7 C6 132.6(4) . . ?
C7 C8 H8 127.3 . . ?
C9 C8 C7 105.3(4) . . ?
C9 C8 H8 127.3 . . ?
N6 C9 C8 107.0(4) . . ?
N6 C9 H9A 126.5 . . ?
C8 C9 H9A 126.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 110.7(4) . . ?
N7 C11 C15 124.7(5) . . ?
C12 C11 C15 124.5(4) . . ?
N8 C12 C11 118.9(4) . . ?
N8 C12 C13 110.5(4) . . ?
C13 C12 C11 130.6(5) . . ?
C12 C13 H13 127.6 . . ?
C14 C13 C12 104.9(5) . . ?
C14 C13 H13 127.6 . . ?
N9 C14 C13 108.3(5) . . ?
N9 C14 H14 125.9 . . ?
C13 C14 H14 125.9 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.0(5) . . ?
C17 C16 B1 120.5(5) . . ?
C21 C16 B1 122.5(5) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(5) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(5) . . ?
C21 C20 H20 120.7 . . ?
C16 C21 H21 118.5 . . ?
C20 C21 C16 123.1(5) . . ?
C20 C21 H21 118.5 . . ?
O1 B1 O2 113.0(4) . . ?
O1 B1 O3 111.5(4) . . ?
O1 B1 C16 106.5(4) . . ?
O2 B1 C16 107.5(4) . . ?
O3 B1 O2 109.7(4) . . ?
O3 B1 C16 108.4(4) . . ?
C1S O1S C4S 103.2(11) . . ?
O1S C1S H1SA 110.6 . . ?
O1S C1S H1SB 110.6 . . ?
O1S C1S C2S 105.9(10) . . ?
H1SA C1S H1SB 108.7 . . ?
C2S C1S H1SA 110.6 . . ?
C2S C1S H1SB 110.6 . . ?
C1S C2S H2SA 110.6 . . ?
C1S C2S H2SB 110.6 . . ?
C1S C2S C3S 105.6(11) . . ?
H2SA C2S H2SB 108.8 . . ?
C3S C2S H2SA 110.6 . . ?
C3S C2S H2SB 110.6 . . ?
C2S C3S H3SA 110.7 . . ?
C2S C3S H3SB 110.7 . . ?
H3SA C3S H3SB 108.8 . . ?
C4S C3S C2S 105.1(12) . . ?
C4S C3S H3SA 110.7 . . ?
C4S C3S H3SB 110.7 . . ?
O1S C4S H4SA 110.3 . . ?
O1S C4S H4SB 110.3 . . ?
C3S C4S O1S 107.0(11) . . ?
C3S C4S H4SA 110.3 . . ?
C3S C4S H4SB 110.3 . . ?
H4SA C4S H4SB 108.6 . . ?
C1S' O1S' C4S' 104.7(17) . . ?
O1S' C1S' H1SC 110.3 . . ?
O1S' C1S' H1SD 110.3 . . ?
O1S' C1S' C2S' 106.9(17) . . ?
H1SC C1S' H1SD 108.6 . . ?
C2S' C1S' H1SC 110.3 . . ?
C2S' C1S' H1SD 110.3 . . ?
C1S' C2S' H2SC 111.1 . . ?
C1S' C2S' H2SD 111.1 . . ?
H2SC C2S' H2SD 109.0 . . ?
C3S' C2S' C1S' 103.4(19) . . ?
C3S' C2S' H2SC 111.1 . . ?
C3S' C2S' H2SD 111.1 . . ?
C2S' C3S' H3SC 109.9 . . ?
C2S' C3S' H3SD 109.9 . . ?
H3SC C3S' H3SD 108.3 . . ?
C4S' C3S' C2S' 109(2) . . ?
C4S' C3S' H3SC 109.9 . . ?
C4S' C3S' H3SD 109.9 . . ?
O1S' C4S' H4SC 110.6 . . ?
O1S' C4S' H4SD 110.6 . . ?
C3S' C4S' O1S' 105(2) . . ?
C3S' C4S' H4SC 110.6 . . ?
C3S' C4S' H4SD 110.6 . . ?
H4SC C4S' H4SD 108.8 . . ?

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 C1 C2 1.1(5) . . . . ?
Co1 N1 C1 C5 -179.8(4) . . . . ?
Co1 N2 N3 C4 174.0(4) . . . . ?
Co1 N2 C2 C1 0.6(5) . . . . ?
Co1 N2 C2 C3 -176.0(3) . . . . ?
Co1 N4 C6 C7 -3.5(6) . . . . ?
Co1 N4 C6 C10 175.3(4) . . . . ?
Co1 N5 N6 C9 175.7(4) . . . . ?
Co1 N5 C7 C6 1.2(6) . . . . ?
Co1 N5 C7 C8 -177.0(3) . . . . ?
Co1 N7 C11 C12 1.9(6) . . . . ?
Co1 N7 C11 C15 -175.6(4) . . . . ?
Co1 N8 N9 C14 -170.0(4) . . . . ?
Co1 N8 C12 C11 -7.2(6) . . . . ?
Co1 N8 C12 C13 173.2(3) . . . . ?
O1 N7 C11 C12 179.1(4) . . . . ?
O1 N7 C11 C15 1.6(7) . . . . ?
O2 N4 C6 C7 -179.9(4) . . . . ?
O2 N4 C6 C10 -1.2(7) . . . . ?
O3 N1 C1 C2 -178.4(4) . . . . ?
O3 N1 C1 C5 0.6(7) . . . . ?
N1 O3 B1 O1 -62.9(5) . . . . ?
N1 O3 B1 O2 63.0(5) . . . . ?
N1 O3 B1 C16 -179.9(4) . . . . ?
N1 C1 C2 N2 -1.1(6) . . . . ?
N1 C1 C2 C3 174.6(5) . . . . ?
N2 N3 C4 C3 0.2(6) . . . . ?
N2 C2 C3 C4 0.3(6) . . . . ?
N3 N2 C2 C1 176.4(4) . . . . ?
N3 N2 C2 C3 -0.2(5) . . . . ?
N4 O2 B1 O1 64.4(5) . . . . ?
N4 O2 B1 O3 -60.6(5) . . . . ?
N4 O2 B1 C16 -178.4(4) . . . . ?
N4 C6 C7 N5 1.4(7) . . . . ?
N4 C6 C7 C8 179.1(5) . . . . ?
N5 N6 C9 C8 -0.3(6) . . . . ?
N5 C7 C8 C9 0.3(6) . . . . ?
N6 N5 C7 C6 177.8(4) . . . . ?
N6 N5 C7 C8 -0.5(5) . . . . ?
N7 O1 B1 O2 -63.5(5) . . . . ?
N7 O1 B1 O3 60.5(5) . . . . ?
N7 O1 B1 C16 178.6(4) . . . . ?
N7 C11 C12 N8 3.7(6) . . . . ?
N7 C11 C12 C13 -176.8(5) . . . . ?
N8 N9 C14 C13 0.5(6) . . . . ?
N8 C12 C13 C14 -0.5(6) . . . . ?
N9 N8 C12 C11 -179.7(4) . . . . ?
N9 N8 C12 C13 0.8(5) . . . . ?
C1 C2 C3 C4 -175.7(5) . . . . ?
C2 N2 N3 C4 0.0(5) . . . . ?
C2 C3 C4 N3 -0.3(6) . . . . ?
C5 C1 C2 N2 179.8(4) . . . . ?
C5 C1 C2 C3 -4.5(8) . . . . ?
C6 C7 C8 C9 -177.6(5) . . . . ?
C7 N5 N6 C9 0.5(5) . . . . ?
C7 C8 C9 N6 0.0(6) . . . . ?
C10 C6 C7 N5 -177.4(5) . . . . ?
C10 C6 C7 C8 0.3(9) . . . . ?
C11 C12 C13 C14 -180.0(5) . . . . ?
C12 N8 N9 C14 -0.8(6) . . . . ?
C12 C13 C14 N9 0.0(6) . . . . ?
C15 C11 C12 N8 -178.8(5) . . . . ?
C15 C11 C12 C13 0.7(8) . . . . ?
C16 C17 C18 C19 1.2(8) . . . . ?
C17 C16 C21 C20 1.8(8) . . . . ?
C17 C16 B1 O1 -178.7(4) . . . . ?
C17 C16 B1 O2 59.9(6) . . . . ?
C17 C16 B1 O3 -58.6(6) . . . . ?
C17 C18 C19 C20 -1.2(8) . . . . ?
C18 C19 C20 C21 1.4(8) . . . . ?
C19 C20 C21 C16 -1.8(8) . . . . ?
C21 C16 C17 C18 -1.4(7) . . . . ?
C21 C16 B1 O1 3.5(7) . . . . ?
C21 C16 B1 O2 -117.9(5) . . . . ?
C21 C16 B1 O3 123.5(5) . . . . ?
B1 O1 N7 Co1 4.8(5) . . . . ?
B1 O1 N7 C11 -172.3(4) . . . . ?
B1 O2 N4 Co1 -5.4(5) . . . . ?
B1 O2 N4 C6 170.9(4) . . . . ?
B1 O3 N1 Co1 -0.3(5) . . . . ?
B1 O3 N1 C1 179.2(4) . . . . ?
B1 C16 C17 C18 -179.4(5) . . . . ?
B1 C16 C21 C20 179.7(5) . . . . ?
O1S C1S C2S C3S -13.5(16) . . . . ?
C1S O1S C4S C3S -37.6(14) . . . . ?
C1S C2S C3S C4S -9.4(15) . . . . ?
C2S C3S C4S O1S 28.9(15) . . . . ?
C4S O1S C1S C2S 30.5(14) . . . . ?
O1S' C1S' C2S' C3S' 17(3) . . . . ?
C1S' O1S' C4S' C3S' 32(2) . . . . ?
C1S' C2S' C3S' C4S' 3(3) . . . . ?
C2S' C3S' C4S' O1S' -22(2) . . . . ?
C4S' O1S' C1S' C2S' -30(3) . . . . ?

_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_ab401
_database_code_depnum_ccdc_archive 'CCDC 2286578'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 B Co N9 O3, Cl, C6 H6'
_chemical_formula_sum            'C27 H29 B Cl Co N9 O3'
_chemical_formula_weight         632.78
_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 0.0042 0.0021 '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'
B B 0.0021 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1754 0.1982 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3446 1.1871 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0081 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0139 0.0077 '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                   8.1600(16)
_cell_length_b                   13.400(3)
_cell_length_c                   13.690(3)
_cell_angle_alpha                92.98(3)
_cell_angle_beta                 102.15(3)
_cell_angle_gamma                96.45(3)
_cell_volume                     1449.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4716
_cell_measurement_temperature    100
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21240
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        28.400
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7927
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5463
_reflns_number_total             6059
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6059
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.029
_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)+(0.0473P)²+0.5046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3S-C2S \\sim C1S'-C2S'
 with sigma of 0.02
 C1S'-C6S' \\sim C2S-C1S
 with sigma of 0.02
 C1S'-C6S' \\sim C6S-C1S
 with sigma of 0.02
 C5S'-C6S' \\sim C5S-C6S
 with sigma of 0.02
 C5S'-C4S' \\sim C4S-C5S
 with sigma of 0.02
 C4S'-C3S' \\sim C3S-C4S
 with sigma of 0.02
 C2S'-C3S' \\sim C3S-C2S
 with sigma of 0.02
 C1S'-C2S' \\sim C2S-C1S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4S) \\sim Ueq, Uanis(C4S') \\sim Ueq, Uanis(C3S') \\sim Ueq, Uanis(C3S)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C3S) \\sim Ueq, Uanis(C3S') \\sim Ueq, Uanis(C4S) \\sim Ueq, Uanis(C4S')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1S') = Uanis(C1S)
Uanis(C6S') = Uanis(C6S)
Uanis(C5S') = Uanis(C5S)
Uanis(C4S) = Uanis(C4S')
Uanis(C3S') = Uanis(C3S)
Uanis(C2S') = Uanis(C2S)
4. Others
 Sof(C1S')=Sof(H1S')=Sof(C2S')=Sof(H2S')=Sof(C3S')=Sof(H3S')=Sof(C4S')=
 Sof(H4S')=Sof(C5S')=Sof(H5S')=Sof(C6S')=Sof(H6S')=1-FVAR(1)
 Sof(C1S)=Sof(H1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=Sof(C4S)=Sof(H4S)=
 Sof(C5S)=Sof(H5S)=Sof(C6S)=Sof(H6S)=FVAR(1)
5.a Riding coordinates:
 N3(H3), N6(H6), N9(H9)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C1S(H1S), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S),
  C6S(H6S), C1S'(H1S'), C2S'(H2S'), C3S'(H3S'), C4S'(H4S'), C5S'(H5S'),
 C6S'(H6S')
5.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.51395(3) 0.66517(2) 0.30689(2) 0.03399(8) Uani 1 1 d . . . . .
O1 O 0.57171(14) 0.47088(9) 0.19001(9) 0.0407(3) Uani 1 1 d . . . . .
O2 O 0.32559(15) 0.44685(9) 0.26981(9) 0.0410(3) Uani 1 1 d . . . . .
O3 O 0.30694(15) 0.53453(9) 0.11536(9) 0.0404(3) Uani 1 1 d . . . . .
N1 N 0.64698(17) 0.55933(11) 0.24425(10) 0.0360(3) Uani 1 1 d . . . . .
N2 N 0.77461(17) 0.72754(11) 0.34662(11) 0.0388(3) Uani 1 1 d . . . . .
N3 N 0.87474(19) 0.80689(12) 0.40030(12) 0.0455(3) Uani 1 1 d . . . . .
H3 H 0.8394 0.8562 0.4300 0.055 Uiso 1 1 d R U . . .
N4 N 0.37214(17) 0.53028(11) 0.33637(11) 0.0372(3) Uani 1 1 d . . . . .
N5 N 0.46167(19) 0.69251(12) 0.45215(11) 0.0425(3) Uani 1 1 d . . . . .
N6 N 0.4925(2) 0.76704(14) 0.52586(12) 0.0535(4) Uani 1 1 d . . . . .
H6 H 0.5555 0.8322 0.5194 0.064 Uiso 1 1 d R U . . .
N7 N 0.34300(17) 0.62925(10) 0.16484(10) 0.0361(3) Uani 1 1 d . . . . .
N8 N 0.42128(18) 0.80405(11) 0.26293(11) 0.0401(3) Uani 1 1 d . . . . .
N9 N 0.4240(2) 0.89820(12) 0.30293(13) 0.0496(4) Uani 1 1 d . . . . .
H9 H 0.4969 0.9241 0.3643 0.059 Uiso 1 1 d R U . . .
C1 C 0.8059(2) 0.58094(13) 0.24766(13) 0.0364(3) Uani 1 1 d . . . . .
C2 C 0.8790(2) 0.67415(13) 0.30832(12) 0.0358(3) Uani 1 1 d . . . . .
C3 C 1.0455(2) 0.72021(15) 0.33800(15) 0.0452(4) Uani 1 1 d . . . . .
H3A H 1.1432 0.6980 0.3211 0.054 Uiso 1 1 calc R U . . .
C4 C 1.0371(2) 0.80473(15) 0.39702(16) 0.0508(5) Uani 1 1 d . . . . .
H4 H 1.1295 0.8528 0.4296 0.061 Uiso 1 1 calc R U . . .
C5 C 0.9064(2) 0.51943(15) 0.19487(17) 0.0500(5) Uani 1 1 d . . . . .
H5A H 0.8951 0.4502 0.2147 0.075 Uiso 1 1 calc R U . . .
H5B H 1.0256 0.5482 0.2129 0.075 Uiso 1 1 calc R U . . .
H5C H 0.8648 0.5194 0.1223 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3177(2) 0.52519(14) 0.41800(13) 0.0393(4) Uani 1 1 d . . . . .
C7 C 0.3710(2) 0.61632(15) 0.48463(13) 0.0416(4) Uani 1 1 d . . . . .
C8 C 0.3457(3) 0.64327(18) 0.57968(15) 0.0553(5) Uani 1 1 d . . . . .
H8 H 0.2862 0.6034 0.6195 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4252(3) 0.7395(2) 0.60296(17) 0.0646(6) Uani 1 1 d . . . . .
H9A H 0.4315 0.7798 0.6632 0.078 Uiso 1 1 calc R U . . .
C10 C 0.2078(3) 0.43766(17) 0.44270(16) 0.0522(5) Uani 1 1 d . . . . .
H10A H 0.0891 0.4442 0.4146 0.078 Uiso 1 1 calc R U . . .
H10B H 0.2256 0.4362 0.5156 0.078 Uiso 1 1 calc R U . . .
H10C H 0.2367 0.3751 0.4141 0.078 Uiso 1 1 calc R U . . .
C11 C 0.2687(2) 0.69819(13) 0.11849(13) 0.0387(4) Uani 1 1 d . . . . .
C12 C 0.3086(2) 0.79649(13) 0.17538(13) 0.0401(4) Uani 1 1 d . . . . .
C13 C 0.2411(3) 0.88698(16) 0.15966(17) 0.0549(5) Uani 1 1 d . . . . .
H13 H 0.1597 0.9019 0.1036 0.066 Uiso 1 1 calc R U . . .
C14 C 0.3183(3) 0.94957(16) 0.24298(18) 0.0598(5) Uani 1 1 d . . . . .
H14 H 0.2999 1.0173 0.2558 0.072 Uiso 1 1 calc R U . . .
C15 C 0.1503(3) 0.68144(17) 0.01892(16) 0.0597(6) Uani 1 1 d . . . . .
H15A H 0.2063 0.6511 -0.0298 0.089 Uiso 1 1 calc R U . . .
H15B H 0.1167 0.7460 -0.0030 0.089 Uiso 1 1 calc R U . . .
H15C H 0.0499 0.6361 0.0239 0.089 Uiso 1 1 calc R U . . .
C16 C 0.3233(2) 0.34880(13) 0.10926(13) 0.0386(4) Uani 1 1 d . . . . .
C17 C 0.3545(2) 0.33473(15) 0.01317(15) 0.0464(4) Uani 1 1 d . . . . .
H17 H 0.4111 0.3889 -0.0140 0.056 Uiso 1 1 calc R U . . .
C18 C 0.3044(3) 0.24314(17) -0.04328(17) 0.0562(5) Uani 1 1 d . . . . .
H18 H 0.3267 0.2352 -0.1084 0.067 Uiso 1 1 calc R U . . .
C19 C 0.2218(3) 0.16303(16) -0.00483(18) 0.0582(5) Uani 1 1 d . . . . .
H19 H 0.1879 0.1002 -0.0433 0.070 Uiso 1 1 calc R U . . .
C20 C 0.1894(3) 0.17536(15) 0.08977(17) 0.0552(5) Uani 1 1 d . . . . .
H20 H 0.1324 0.1210 0.1164 0.066 Uiso 1 1 calc R U . . .
C21 C 0.2400(2) 0.26697(14) 0.14606(15) 0.0463(4) Uani 1 1 d . . . . .
H21 H 0.2174 0.2742 0.2112 0.056 Uiso 1 1 calc R U . . .
B1 B 0.3835(2) 0.45447(15) 0.17413(15) 0.0366(4) Uani 1 1 d . . . . .
Cl1 Cl 0.70751(6) 0.96484(4) 0.50177(4) 0.05614(14) Uani 1 1 d . . . . .
C1S C 0.0961(7) 0.9447(4) 0.7093(4) 0.0604(11) Uani 0.623(5) 1 d D . P A 1
H1S H 0.0298 0.9831 0.6637 0.073 Uiso 0.623(5) 1 calc R U P A 1
C2S C 0.0576(7) 0.8433(4) 0.7036(4) 0.0612(11) Uani 0.623(5) 1 d D . P A 1
H2S H -0.0395 0.8110 0.6571 0.073 Uiso 0.623(5) 1 calc R U P A 1
C3S C 0.1616(9) 0.7867(4) 0.7664(5) 0.0700(14) Uani 0.623(5) 1 d D U P A 1
H3S H 0.1380 0.7154 0.7617 0.084 Uiso 0.623(5) 1 calc R U P A 1
C4S C 0.3047(10) 0.8372(6) 0.8383(7) 0.082(2) Uani 0.623(5) 1 d D U P A 1
H4S H 0.3794 0.7999 0.8801 0.099 Uiso 0.623(5) 1 calc R U P A 1
C5S C 0.332(2) 0.9418(9) 0.8454(9) 0.085(2) Uani 0.623(5) 1 d D . P A 1
H5S H 0.4206 0.9773 0.8955 0.101 Uiso 0.623(5) 1 calc R U P A 1
C6S C 0.2301(15) 0.9922(9) 0.7805(9) 0.080(2) Uani 0.623(5) 1 d D . P A 1
H6S H 0.2522 1.0636 0.7840 0.096 Uiso 0.623(5) 1 calc R U P A 1
C1S' C 0.0767(14) 0.9049(8) 0.7078(9) 0.0604(11) Uani 0.377(5) 1 d D . P A 2
H1S' H -0.0207 0.9171 0.6604 0.073 Uiso 0.377(5) 1 calc R U P A 2
C2S' C 0.1099(12) 0.8077(8) 0.7225(7) 0.0612(11) Uani 0.377(5) 1 d D . P A 2
H2S' H 0.0380 0.7538 0.6818 0.073 Uiso 0.377(5) 1 calc R U P A 2
C3S' C 0.2488(16) 0.7855(7) 0.7967(8) 0.0700(14) Uani 0.377(5) 1 d D U P A 2
H3S' H 0.2701 0.7186 0.8093 0.084 Uiso 0.377(5) 1 calc R U P A 2
C4S' C 0.3510(19) 0.8699(13) 0.8493(14) 0.082(2) Uani 0.377(5) 1 d D U P A 2
H4S' H 0.4454 0.8619 0.9009 0.099 Uiso 0.377(5) 1 calc R U P A 2
C5S' C 0.315(4) 0.9633(17) 0.8266(19) 0.085(2) Uani 0.377(5) 1 d D . P A 2
H5S' H 0.3915 1.0191 0.8607 0.101 Uiso 0.377(5) 1 calc R U P A 2
C6S' C 0.182(3) 0.9822(16) 0.7605(19) 0.080(2) Uani 0.377(5) 1 d D . P A 2
H6S' H 0.1607 1.0496 0.7504 0.096 Uiso 0.377(5) 1 calc R U P A 2


_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 2.1298(15) . ?
Co1 N2 2.1412(15) . ?
Co1 N4 2.1382(16) . ?
Co1 N5 2.1417(15) . ?
Co1 N7 2.1375(16) . ?
Co1 N8 2.1538(16) . ?
O1 N1 1.3733(18) . ?
O1 B1 1.495(2) . ?
O2 N4 1.3701(19) . ?
O2 B1 1.487(2) . ?
O3 N7 1.3782(18) . ?
O3 B1 1.489(2) . ?
N1 C1 1.287(2) . ?
N2 N3 1.345(2) . ?
N2 C2 1.341(2) . ?
N3 H3 0.8657 . ?
N3 C4 1.338(2) . ?
N4 C6 1.289(2) . ?
N5 N6 1.346(2) . ?
N5 C7 1.343(2) . ?
N6 H6 0.9802 . ?
N6 C9 1.338(3) . ?
N7 C11 1.284(2) . ?
N8 N9 1.345(2) . ?
N8 C12 1.340(2) . ?
N9 H9 0.9450 . ?
N9 C14 1.336(3) . ?
C1 C2 1.456(2) . ?
C1 C5 1.488(2) . ?
C2 C3 1.395(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.453(3) . ?
C6 C10 1.492(3) . ?
C7 C8 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.367(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.462(2) . ?
C11 C15 1.486(3) . ?
C12 C13 1.395(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.399(3) . ?
C16 C21 1.397(3) . ?
C16 B1 1.601(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9500 . ?
C1S H1S 0.9500 . ?
C1S C2S 1.354(5) . ?
C1S C6S 1.372(7) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.393(6) . ?
C3S H3S 0.9500 . ?
C3S C4S 1.435(9) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.389(10) . ?
C5S H5S 0.9500 . ?
C5S C6S 1.346(9) . ?
C6S H6S 0.9500 . ?
C1S' H1S' 0.9500 . ?
C1S' C2S' 1.376(10) . ?
C1S' C6S' 1.338(12) . ?
C2S' H2S' 0.9500 . ?
C2S' C3S' 1.424(9) . ?
C3S' H3S' 0.9500 . ?
C3S' C4S' 1.394(14) . ?
C4S' H4S' 0.9500 . ?
C4S' C5S' 1.354(14) . ?
C5S' H5S' 0.9500 . ?
C5S' C6S' 1.319(15) . ?
C6S' H6S' 0.9500 . ?

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 N2 74.34(6) . . ?
N1 Co1 N4 81.85(6) . . ?
N1 Co1 N5 134.00(6) . . ?
N1 Co1 N7 81.16(6) . . ?
N1 Co1 N8 135.15(6) . . ?
N2 Co1 N5 96.32(6) . . ?
N2 Co1 N8 95.28(6) . . ?
N4 Co1 N2 134.81(6) . . ?
N4 Co1 N5 73.57(6) . . ?
N4 Co1 N8 127.78(6) . . ?
N5 Co1 N8 89.88(6) . . ?
N7 Co1 N2 131.84(6) . . ?
N7 Co1 N4 79.59(6) . . ?
N7 Co1 N5 129.59(6) . . ?
N7 Co1 N8 74.02(6) . . ?
N1 O1 B1 114.64(12) . . ?
N4 O2 B1 115.52(13) . . ?
N7 O3 B1 114.19(12) . . ?
O1 N1 Co1 124.31(10) . . ?
C1 N1 Co1 119.93(12) . . ?
C1 N1 O1 115.44(14) . . ?
N3 N2 Co1 140.15(12) . . ?
C2 N2 Co1 114.70(11) . . ?
C2 N2 N3 105.15(14) . . ?
N2 N3 H3 124.9 . . ?
C4 N3 N2 111.83(15) . . ?
C4 N3 H3 123.1 . . ?
O2 N4 Co1 123.53(10) . . ?
C6 N4 Co1 120.67(13) . . ?
C6 N4 O2 115.71(14) . . ?
N6 N5 Co1 138.70(13) . . ?
C7 N5 Co1 115.85(12) . . ?
C7 N5 N6 105.45(15) . . ?
N5 N6 H6 121.3 . . ?
C9 N6 N5 111.36(18) . . ?
C9 N6 H6 127.4 . . ?
O3 N7 Co1 124.28(10) . . ?
C11 N7 Co1 120.44(12) . . ?
C11 N7 O3 115.27(14) . . ?
N9 N8 Co1 138.84(12) . . ?
C12 N8 Co1 114.96(12) . . ?
C12 N8 N9 105.47(15) . . ?
N8 N9 H9 122.8 . . ?
C14 N9 N8 111.48(16) . . ?
C14 N9 H9 125.6 . . ?
N1 C1 C2 112.75(15) . . ?
N1 C1 C5 124.57(16) . . ?
C2 C1 C5 122.68(15) . . ?
N2 C2 C1 117.79(14) . . ?
N2 C2 C3 110.72(16) . . ?
C3 C2 C1 131.47(16) . . ?
C2 C3 H3A 127.6 . . ?
C4 C3 C2 104.85(16) . . ?
C4 C3 H3A 127.6 . . ?
N3 C4 C3 107.44(16) . . ?
N3 C4 H4 126.3 . . ?
C3 C4 H4 126.3 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 112.67(16) . . ?
N4 C6 C10 124.99(17) . . ?
C7 C6 C10 122.33(16) . . ?
N5 C7 C6 117.17(15) . . ?
N5 C7 C8 110.35(18) . . ?
C8 C7 C6 132.48(18) . . ?
C7 C8 H8 127.5 . . ?
C9 C8 C7 104.98(19) . . ?
C9 C8 H8 127.5 . . ?
N6 C9 C8 107.85(19) . . ?
N6 C9 H9A 126.1 . . ?
C8 C9 H9A 126.1 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 112.90(15) . . ?
N7 C11 C15 124.61(17) . . ?
C12 C11 C15 122.46(16) . . ?
N8 C12 C11 117.58(15) . . ?
N8 C12 C13 110.49(16) . . ?
C13 C12 C11 131.75(17) . . ?
C12 C13 H13 127.6 . . ?
C14 C13 C12 104.81(18) . . ?
C14 C13 H13 127.6 . . ?
N9 C14 C13 107.74(18) . . ?
N9 C14 H14 126.1 . . ?
C13 C14 H14 126.1 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 B1 120.78(16) . . ?
C21 C16 C17 117.34(17) . . ?
C21 C16 B1 121.88(16) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.23(19) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.48(19) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.59(19) . . ?
C20 C21 H21 119.2 . . ?
O1 B1 C16 106.16(14) . . ?
O2 B1 O1 112.46(14) . . ?
O2 B1 O3 111.29(14) . . ?
O2 B1 C16 107.82(14) . . ?
O3 B1 O1 110.58(14) . . ?
O3 B1 C16 108.28(14) . . ?
C2S C1S H1S 119.7 . . ?
C2S C1S C6S 120.5(8) . . ?
C6S C1S H1S 119.7 . . ?
C1S C2S H2S 120.3 . . ?
C1S C2S C3S 119.5(5) . . ?
C3S C2S H2S 120.3 . . ?
C2S C3S H3S 120.3 . . ?
C2S C3S C4S 119.4(6) . . ?
C4S C3S H3S 120.3 . . ?
C3S C4S H4S 120.7 . . ?
C5S C4S C3S 118.7(9) . . ?
C5S C4S H4S 120.7 . . ?
C4S C5S H5S 120.4 . . ?
C6S C5S C4S 119.2(13) . . ?
C6S C5S H5S 120.4 . . ?
C1S C6S H6S 118.7 . . ?
C5S C6S C1S 122.6(12) . . ?
C5S C6S H6S 118.7 . . ?
C2S' C1S' H1S' 120.1 . . ?
C6S' C1S' H1S' 120.1 . . ?
C6S' C1S' C2S' 119.9(14) . . ?
C1S' C2S' H2S' 119.0 . . ?
C1S' C2S' C3S' 122.0(9) . . ?
C3S' C2S' H2S' 119.0 . . ?
C2S' C3S' H3S' 122.7 . . ?
C4S' C3S' C2S' 114.6(11) . . ?
C4S' C3S' H3S' 122.7 . . ?
C3S' C4S' H4S' 120.1 . . ?
C5S' C4S' C3S' 119.8(19) . . ?
C5S' C4S' H4S' 120.1 . . ?
C4S' C5S' H5S' 117.7 . . ?
C6S' C5S' C4S' 125(3) . . ?
C6S' C5S' H5S' 117.7 . . ?
C1S' C6S' H6S' 120.5 . . ?
C5S' C6S' C1S' 119(2) . . ?
C5S' C6S' H6S' 120.5 . . ?

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 C1 C2 7.8(2) . . . . ?
Co1 N1 C1 C5 -171.42(15) . . . . ?
Co1 N2 N3 C4 179.78(16) . . . . ?
Co1 N2 C2 C1 -1.4(2) . . . . ?
Co1 N2 C2 C3 180.00(12) . . . . ?
Co1 N4 C6 C7 -3.0(2) . . . . ?
Co1 N4 C6 C10 175.52(14) . . . . ?
Co1 N5 N6 C9 -179.96(17) . . . . ?
Co1 N5 C7 C6 -0.6(2) . . . . ?
Co1 N5 C7 C8 179.94(13) . . . . ?
Co1 N7 C11 C12 -2.8(2) . . . . ?
Co1 N7 C11 C15 178.90(16) . . . . ?
Co1 N8 N9 C14 -169.61(17) . . . . ?
Co1 N8 C12 C11 -3.0(2) . . . . ?
Co1 N8 C12 C13 172.70(14) . . . . ?
O1 N1 C1 C2 -178.52(13) . . . . ?
O1 N1 C1 C5 2.3(3) . . . . ?
O2 N4 C6 C7 -179.69(13) . . . . ?
O2 N4 C6 C10 -1.2(3) . . . . ?
O3 N7 C11 C12 178.68(14) . . . . ?
O3 N7 C11 C15 0.4(3) . . . . ?
N1 O1 B1 O2 -62.80(19) . . . . ?
N1 O1 B1 O3 62.29(18) . . . . ?
N1 O1 B1 C16 179.52(13) . . . . ?
N1 C1 C2 N2 -4.0(2) . . . . ?
N1 C1 C2 C3 174.22(19) . . . . ?
N2 N3 C4 C3 0.3(2) . . . . ?
N2 C2 C3 C4 0.2(2) . . . . ?
N3 N2 C2 C1 178.51(15) . . . . ?
N3 N2 C2 C3 -0.1(2) . . . . ?
N4 O2 B1 O1 61.03(19) . . . . ?
N4 O2 B1 O3 -63.68(18) . . . . ?
N4 O2 B1 C16 177.71(12) . . . . ?
N4 C6 C7 N5 2.3(2) . . . . ?
N4 C6 C7 C8 -178.4(2) . . . . ?
N5 N6 C9 C8 -0.3(3) . . . . ?
N5 C7 C8 C9 0.1(2) . . . . ?
N6 N5 C7 C6 179.17(15) . . . . ?
N6 N5 C7 C8 -0.3(2) . . . . ?
N7 O3 B1 O1 -66.75(17) . . . . ?
N7 O3 B1 O2 59.00(18) . . . . ?
N7 O3 B1 C16 177.33(13) . . . . ?
N7 C11 C12 N8 3.8(2) . . . . ?
N7 C11 C12 C13 -170.8(2) . . . . ?
N8 N9 C14 C13 0.3(3) . . . . ?
N8 C12 C13 C14 -0.5(3) . . . . ?
N9 N8 C12 C11 -175.06(16) . . . . ?
N9 N8 C12 C13 0.6(2) . . . . ?
C1 C2 C3 C4 -178.08(19) . . . . ?
C2 N2 N3 C4 -0.1(2) . . . . ?
C2 C3 C4 N3 -0.3(2) . . . . ?
C5 C1 C2 N2 175.22(17) . . . . ?
C5 C1 C2 C3 -6.6(3) . . . . ?
C6 C7 C8 C9 -179.2(2) . . . . ?
C7 N5 N6 C9 0.4(2) . . . . ?
C7 C8 C9 N6 0.1(3) . . . . ?
C10 C6 C7 N5 -176.26(17) . . . . ?
C10 C6 C7 C8 3.1(3) . . . . ?
C11 C12 C13 C14 174.4(2) . . . . ?
C12 N8 N9 C14 -0.6(2) . . . . ?
C12 C13 C14 N9 0.1(3) . . . . ?
C15 C11 C12 N8 -177.86(19) . . . . ?
C15 C11 C12 C13 7.5(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C16 C21 C20 -0.2(3) . . . . ?
C17 C16 B1 O1 -61.7(2) . . . . ?
C17 C16 B1 O2 177.59(16) . . . . ?
C17 C16 B1 O3 57.1(2) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 0.4(3) . . . . ?
C21 C16 C17 C18 0.1(3) . . . . ?
C21 C16 B1 O1 117.56(18) . . . . ?
C21 C16 B1 O2 -3.2(2) . . . . ?
C21 C16 B1 O3 -123.67(18) . . . . ?
B1 O1 N1 Co1 2.03(19) . . . . ?
B1 O1 N1 C1 -171.38(15) . . . . ?
B1 O2 N4 Co1 1.23(18) . . . . ?
B1 O2 N4 C6 177.85(15) . . . . ?
B1 O3 N7 Co1 6.27(18) . . . . ?
B1 O3 N7 C11 -175.30(15) . . . . ?
B1 C16 C17 C18 179.36(18) . . . . ?
B1 C16 C21 C20 -179.49(17) . . . . ?
C1S C2S C3S C4S 2.0(8) . . . . ?
C2S C1S C6S C5S 2(2) . . . . ?
C2S C3S C4S C5S 2.3(13) . . . . ?
C3S C4S C5S C6S -4(2) . . . . ?
C4S C5S C6S C1S 3(2) . . . . ?
C6S C1S C2S C3S -4.1(12) . . . . ?
C1S' C2S' C3S' C4S' -2.7(16) . . . . ?
C2S' C1S' C6S' C5S' -1(4) . . . . ?
C2S' C3S' C4S' C5S' -1(3) . . . . ?
C3S' C4S' C5S' C6S' 4(4) . . . . ?
C4S' C5S' C6S' C1S' -3(5) . . . . ?
C6S' C1S' C2S' C3S' 4(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_ss116_co
_database_code_depnum_ccdc_archive 'CCDC 2286465'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-07-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 B Co N9 O3, Cl'
_chemical_formula_sum            'C18 H17 B Cl Co N9 O3'
_chemical_formula_weight         512.59
_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'
B B 0.0013 0.0007 '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'
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      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                   9.1009(7)
_cell_length_b                   14.2006(10)
_cell_length_c                   16.7978(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.580(2)
_cell_angle_gamma                90
_cell_volume                     2134.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5982
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0958 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.8333.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         1.891
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                4931
_reflns_number_total             6214
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+1.4859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N3(H3), N6(H6), N9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9A), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_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 0.31649(3) 0.83317(2) 0.07587(2) 0.01221(7) Uani 1 1 d . . . . .
Cl1 Cl 0.63797(5) 0.63680(3) -0.03665(3) 0.02103(10) Uani 1 1 d . . . . .
O1 O 0.01015(14) 0.88222(9) 0.12649(8) 0.0165(3) Uani 1 1 d . . . . .
O2 O 0.22860(14) 0.94579(9) 0.22041(8) 0.0180(3) Uani 1 1 d . . . . .
O3 O 0.14178(14) 1.02080(9) 0.08664(8) 0.0177(3) Uani 1 1 d . . . . .
N1 N 0.08570(17) 0.81975(10) 0.08620(9) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.24102(17) 0.70286(11) 0.01734(9) 0.0149(3) Uani 1 1 d . . . . .
N3 N 0.29230(18) 0.63432(11) -0.02601(10) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.3917 0.6265 -0.0245 0.022 Uiso 1 1 d R U . . .
N4 N 0.33014(17) 0.88629(11) 0.19656(9) 0.0147(3) Uani 1 1 d . . . . .
N5 N 0.51637(17) 0.77355(11) 0.14536(9) 0.0165(3) Uani 1 1 d . . . . .
N6 N 0.63337(18) 0.72103(12) 0.13385(10) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.6377 0.6954 0.0826 0.026 Uiso 1 1 d R U . . .
N7 N 0.23258(17) 0.97071(11) 0.04514(9) 0.0151(3) Uani 1 1 d . . . . .
N8 N 0.41126(17) 0.87307(11) -0.02730(9) 0.0151(3) Uani 1 1 d . . . . .
N9 N 0.49950(18) 0.83918(11) -0.07747(10) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.5387 0.7821 -0.0657 0.022 Uiso 1 1 d R U . . .
C1 C 0.0088(2) 0.75273(12) 0.04877(11) 0.0147(3) Uani 1 1 d . . . . .
H1 H -0.0955 0.7462 0.0476 0.018 Uiso 1 1 calc R U . . .
C2 C 0.0930(2) 0.68736(12) 0.00821(11) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.0508(2) 0.60915(13) -0.04090(12) 0.0198(4) Uani 1 1 d . . . . .
H3A H -0.0467 0.5836 -0.0567 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1817(2) 0.57723(14) -0.06143(13) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.1920 0.5244 -0.0946 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4437(2) 0.86541(13) 0.25091(11) 0.0160(4) Uani 1 1 d . . . . .
H5 H 0.4565 0.8881 0.3049 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5518(2) 0.80364(13) 0.22259(11) 0.0167(4) Uani 1 1 d . . . . .
C7 C 0.6919(2) 0.77049(15) 0.25955(12) 0.0227(4) Uani 1 1 d . . . . .
H7 H 0.7426 0.7818 0.3133 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7404(2) 0.71750(17) 0.20058(12) 0.0261(5) Uani 1 1 d . . . . .
H8 H 0.8326 0.6846 0.2061 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2600(2) 1.00893(13) -0.01934(11) 0.0160(4) Uani 1 1 d . . . . .
H9A H 0.2187 1.0679 -0.0387 0.019 Uiso 1 1 calc R U . . .
C10 C 0.3591(2) 0.95535(13) -0.06068(11) 0.0157(4) Uani 1 1 d . . . . .
C11 C 0.4134(2) 0.97345(14) -0.13124(11) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.3930 1.0266 -0.1659 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5029(2) 0.89786(14) -0.13991(12) 0.0207(4) Uani 1 1 d . . . . .
H12 H 0.5575 0.8886 -0.1824 0.025 Uiso 1 1 calc R U . . .
C13 C -0.0087(2) 1.03657(13) 0.19612(11) 0.0163(4) Uani 1 1 d . . . . .
C14 C -0.0662(2) 1.00501(15) 0.26299(11) 0.0213(4) Uani 1 1 d . . . . .
H14 H -0.0439 0.9428 0.2823 0.026 Uiso 1 1 calc R U . . .
C15 C -0.1550(2) 1.06176(16) 0.30212(12) 0.0261(5) Uani 1 1 d . . . . .
H15 H -0.1928 1.0384 0.3474 0.031 Uiso 1 1 calc R U . . .
C16 C -0.1880(2) 1.15278(15) 0.27452(13) 0.0258(5) Uani 1 1 d . . . . .
H16 H -0.2482 1.1921 0.3011 0.031 Uiso 1 1 calc R U . . .
C17 C -0.1332(2) 1.18647(14) 0.20823(13) 0.0246(4) Uani 1 1 d . . . . .
H17 H -0.1562 1.2487 0.1893 0.029 Uiso 1 1 calc R U . . .
C18 C -0.0444(2) 1.12885(14) 0.16953(12) 0.0204(4) Uani 1 1 d . . . . .
H18 H -0.0072 1.1525 0.1242 0.024 Uiso 1 1 calc R U . . .
B1 B 0.0972(2) 0.96931(15) 0.15515(13) 0.0161(4) 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
Co1 N1 2.1475(15) . ?
Co1 N2 2.1483(15) . ?
Co1 N4 2.1452(15) . ?
Co1 N5 2.1468(15) . ?
Co1 N7 2.1259(15) . ?
Co1 N8 2.1487(16) . ?
O1 N1 1.3743(19) . ?
O1 B1 1.499(2) . ?
O2 N4 1.3653(19) . ?
O2 B1 1.504(2) . ?
O3 N7 1.3735(19) . ?
O3 B1 1.482(2) . ?
N1 C1 1.277(2) . ?
N2 N3 1.349(2) . ?
N2 C2 1.346(2) . ?
N3 H3 0.9073 . ?
N3 C4 1.343(2) . ?
N4 C5 1.282(2) . ?
N5 N6 1.343(2) . ?
N5 C6 1.348(2) . ?
N6 H6 0.9414 . ?
N6 C8 1.344(3) . ?
N7 C9 1.276(2) . ?
N8 N9 1.355(2) . ?
N8 C10 1.344(2) . ?
N9 H9 0.8925 . ?
N9 C12 1.345(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.451(3) . ?
C2 C3 1.395(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.461(3) . ?
C6 C7 1.393(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9500 . ?
C9 C10 1.451(3) . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C13 C18 1.403(3) . ?
C13 B1 1.600(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9500 . ?

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 N2 74.05(6) . . ?
N1 Co1 N8 129.19(6) . . ?
N2 Co1 N8 90.00(6) . . ?
N4 Co1 N1 80.95(6) . . ?
N4 Co1 N2 133.91(6) . . ?
N4 Co1 N5 74.25(6) . . ?
N4 Co1 N8 135.02(6) . . ?
N5 Co1 N1 131.67(6) . . ?
N5 Co1 N2 94.41(6) . . ?
N5 Co1 N8 96.72(6) . . ?
N7 Co1 N1 77.76(6) . . ?
N7 Co1 N2 127.58(6) . . ?
N7 Co1 N4 82.08(6) . . ?
N7 Co1 N5 136.48(6) . . ?
N7 Co1 N8 75.01(6) . . ?
N1 O1 B1 114.07(13) . . ?
N4 O2 B1 114.45(13) . . ?
N7 O3 B1 114.51(13) . . ?
O1 N1 Co1 124.59(11) . . ?
C1 N1 Co1 118.85(13) . . ?
C1 N1 O1 116.42(15) . . ?
N3 N2 Co1 139.05(12) . . ?
C2 N2 Co1 114.98(12) . . ?
C2 N2 N3 105.00(14) . . ?
N2 N3 H3 121.0 . . ?
C4 N3 N2 111.68(16) . . ?
C4 N3 H3 126.9 . . ?
O2 N4 Co1 124.76(10) . . ?
C5 N4 Co1 119.40(13) . . ?
C5 N4 O2 115.77(15) . . ?
N6 N5 Co1 139.11(13) . . ?
N6 N5 C6 105.00(15) . . ?
C6 N5 Co1 115.31(12) . . ?
N5 N6 H6 120.9 . . ?
N5 N6 C8 111.91(17) . . ?
C8 N6 H6 127.0 . . ?
O3 N7 Co1 125.12(11) . . ?
C9 N7 Co1 118.64(13) . . ?
C9 N7 O3 116.10(15) . . ?
N9 N8 Co1 141.23(12) . . ?
C10 N8 Co1 113.71(12) . . ?
C10 N8 N9 104.70(15) . . ?
N8 N9 H9 116.3 . . ?
C12 N9 N8 111.50(16) . . ?
C12 N9 H9 132.1 . . ?
N1 C1 H1 122.6 . . ?
N1 C1 C2 114.78(16) . . ?
C2 C1 H1 122.6 . . ?
N2 C2 C1 116.48(16) . . ?
N2 C2 C3 111.01(16) . . ?
C3 C2 C1 132.50(17) . . ?
C2 C3 H3A 127.7 . . ?
C4 C3 C2 104.69(17) . . ?
C4 C3 H3A 127.7 . . ?
N3 C4 C3 107.63(17) . . ?
N3 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
N4 C5 H5 122.9 . . ?
N4 C5 C6 114.20(17) . . ?
C6 C5 H5 122.9 . . ?
N5 C6 C5 116.57(16) . . ?
N5 C6 C7 111.07(17) . . ?
C7 C6 C5 132.32(18) . . ?
C6 C7 H7 127.7 . . ?
C8 C7 C6 104.59(17) . . ?
C8 C7 H7 127.7 . . ?
N6 C8 C7 107.43(18) . . ?
N6 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
N7 C9 H9A 122.6 . . ?
N7 C9 C10 114.74(16) . . ?
C10 C9 H9A 122.6 . . ?
N8 C10 C9 117.35(16) . . ?
N8 C10 C11 111.26(17) . . ?
C11 C10 C9 131.39(17) . . ?
C10 C11 H11 127.5 . . ?
C12 C11 C10 104.91(17) . . ?
C12 C11 H11 127.5 . . ?
N9 C12 C11 107.63(17) . . ?
N9 C12 H12 126.2 . . ?
C11 C12 H12 126.2 . . ?
C14 C13 C18 117.16(18) . . ?
C14 C13 B1 119.90(17) . . ?
C18 C13 B1 122.90(18) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.04(19) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.16(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.83(19) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
O1 B1 O2 110.69(15) . . ?
O1 B1 C13 107.83(15) . . ?
O2 B1 C13 106.28(15) . . ?
O3 B1 O1 111.20(15) . . ?
O3 B1 O2 112.40(15) . . ?
O3 B1 C13 108.19(15) . . ?

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 C1 C2 5.1(2) . . . . ?
Co1 N2 N3 C4 -167.38(15) . . . . ?
Co1 N2 C2 C1 -8.6(2) . . . . ?
Co1 N2 C2 C3 170.85(13) . . . . ?
Co1 N4 C5 C6 -1.4(2) . . . . ?
Co1 N5 N6 C8 169.96(16) . . . . ?
Co1 N5 C6 C5 5.5(2) . . . . ?
Co1 N5 C6 C7 -172.53(13) . . . . ?
Co1 N7 C9 C10 -5.4(2) . . . . ?
Co1 N8 N9 C12 172.13(15) . . . . ?
Co1 N8 C10 C9 5.7(2) . . . . ?
Co1 N8 C10 C11 -174.52(12) . . . . ?
O1 N1 C1 C2 -178.96(14) . . . . ?
O2 N4 C5 C6 -178.46(14) . . . . ?
O3 N7 C9 C10 178.57(14) . . . . ?
N1 O1 B1 O2 -67.18(19) . . . . ?
N1 O1 B1 O3 58.51(19) . . . . ?
N1 O1 B1 C13 176.96(13) . . . . ?
N1 C1 C2 N2 2.4(2) . . . . ?
N1 C1 C2 C3 -176.8(2) . . . . ?
N2 N3 C4 C3 0.1(2) . . . . ?
N2 C2 C3 C4 0.1(2) . . . . ?
N3 N2 C2 C1 -179.45(15) . . . . ?
N3 N2 C2 C3 0.0(2) . . . . ?
N4 O2 B1 O1 61.62(19) . . . . ?
N4 O2 B1 O3 -63.39(19) . . . . ?
N4 O2 B1 C13 178.44(14) . . . . ?
N4 C5 C6 N5 -2.7(2) . . . . ?
N4 C5 C6 C7 174.7(2) . . . . ?
N5 N6 C8 C7 0.0(2) . . . . ?
N5 C6 C7 C8 -0.4(2) . . . . ?
N6 N5 C6 C5 178.40(16) . . . . ?
N6 N5 C6 C7 0.4(2) . . . . ?
N7 O3 B1 O1 -61.22(19) . . . . ?
N7 O3 B1 O2 63.52(19) . . . . ?
N7 O3 B1 C13 -179.45(13) . . . . ?
N7 C9 C10 N8 -0.3(2) . . . . ?
N7 C9 C10 C11 179.86(19) . . . . ?
N8 N9 C12 C11 -0.2(2) . . . . ?
N8 C10 C11 C12 -0.2(2) . . . . ?
N9 N8 C10 C9 -179.78(15) . . . . ?
N9 N8 C10 C11 0.0(2) . . . . ?
C1 C2 C3 C4 179.38(19) . . . . ?
C2 N2 N3 C4 0.0(2) . . . . ?
C2 C3 C4 N3 -0.1(2) . . . . ?
C5 C6 C7 C8 -178.0(2) . . . . ?
C6 N5 N6 C8 -0.3(2) . . . . ?
C6 C7 C8 N6 0.2(2) . . . . ?
C9 C10 C11 C12 179.64(18) . . . . ?
C10 N8 N9 C12 0.1(2) . . . . ?
C10 C11 C12 N9 0.2(2) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C14 C13 B1 O1 60.0(2) . . . . ?
C14 C13 B1 O2 -58.7(2) . . . . ?
C14 C13 B1 O3 -179.65(16) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C18 C13 B1 O1 -122.04(18) . . . . ?
C18 C13 B1 O2 119.24(18) . . . . ?
C18 C13 B1 O3 -1.7(2) . . . . ?
B1 O1 N1 Co1 7.24(19) . . . . ?
B1 O1 N1 C1 -168.45(15) . . . . ?
B1 O2 N4 Co1 2.83(19) . . . . ?
B1 O2 N4 C5 179.68(16) . . . . ?
B1 O3 N7 Co1 -2.99(19) . . . . ?
B1 O3 N7 C9 172.72(16) . . . . ?
B1 C13 C14 C15 178.05(18) . . . . ?
B1 C13 C18 C17 -177.96(17) . . . . ?

_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_ss370
_database_code_depnum_ccdc_archive 'CCDC 2286463'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-07-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C21 H23 B Co N9 O3'
_chemical_formula_sum            'C21 H23 B Co I N9 O3'
_chemical_formula_weight         646.12
_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'
B B 0.0013 0.0007 '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'
I I -0.4742 1.8119 '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      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                   8.7090(17)
_cell_length_b                   28.144(6)
_cell_length_c                   10.552(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.775(4)
_cell_angle_gamma                90
_cell_volume                     2548.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      23.76
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1521
_diffrn_reflns_av_unetI/netI     0.1110
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22802
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.088
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                2709
_reflns_number_total             4497
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.107
_refine_diff_density_min         -1.945
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4497
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.021
_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)+(0.1095P)²+13.2313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16-B1 \\sim C16'-B1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16') \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C16') \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C18')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19) \\sim Ueq, Uanis(C19') \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C21') = Uanis(C21)
Uanis(C18) = Uanis(C18')
Uanis(C17') = Uanis(C17)
Uanis(C20') = Uanis(C20)
Uanis(C19') = Uanis(C19)
Uanis(C16') = Uanis(C16)
4. Others
 Sof(C16')=Sof(C17')=Sof(H17')=Sof(C18')=Sof(H18')=Sof(C19')=Sof(H19')=
 Sof(C20')=Sof(H20')=Sof(C21')=Sof(H21')=1-FVAR(1)
 Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=
 Sof(H20)=Sof(C21)=Sof(H21)=FVAR(1)
5.a Riding coordinates:
 N3(H3), N6(H6), N9(H9)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C17'(H17'), C18'(H18'), C19'(H19'), C20'(H20'),
 C21'(H21')
5.c Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C21), C16'(C17',C18',C19',C20',C21')
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.10163(10) 0.71432(4) -0.15079(9) 0.0520(4) Uani 1 1 d . . . . .
Co1 Co 0.41098(14) 0.64106(4) 0.26542(12) 0.0160(3) Uani 1 1 d . . . . .
O1 O 0.4406(7) 0.5934(2) 0.5372(6) 0.0207(15) Uani 1 1 d . . . . .
O2 O 0.6691(8) 0.6423(3) 0.5130(6) 0.0262(16) Uani 1 1 d . . . . .
O3 O 0.6330(8) 0.5643(2) 0.4080(6) 0.0225(15) Uani 1 1 d . . . . .
N1 N 0.3388(9) 0.6108(3) 0.4319(7) 0.0158(17) Uani 1 1 d . . . . .
N2 N 0.1614(9) 0.6430(3) 0.2287(8) 0.0238(19) Uani 1 1 d . . . . .
N3 N 0.0437(10) 0.6573(3) 0.1383(9) 0.032(2) Uani 1 1 d . . . . .
H3 H 0.0355 0.6763 0.0686 0.038 Uiso 1 1 d R U . . .
N4 N 0.5911(10) 0.6686(3) 0.4121(8) 0.0234(19) Uani 1 1 d . . . . .
N5 N 0.4403(10) 0.7141(3) 0.2169(8) 0.026(2) Uani 1 1 d . . . . .
N6 N 0.3745(12) 0.7457(3) 0.1295(9) 0.036(2) Uani 1 1 d . . . . .
H6 H 0.2812 0.7469 0.0683 0.043 Uiso 1 1 d R U . . .
N7 N 0.5645(9) 0.5819(3) 0.2903(7) 0.0201(18) Uani 1 1 d . . . . .
N8 N 0.4309(9) 0.6164(3) 0.0722(8) 0.0213(19) Uani 1 1 d . . . . .
N9 N 0.3837(10) 0.6286(3) -0.0517(7) 0.0219(19) Uani 1 1 d . . . . .
H9 H 0.3089 0.6529 -0.0921 0.026 Uiso 1 1 d R U . . .
C1 C 0.1949(11) 0.6077(3) 0.4373(9) 0.019(2) Uani 1 1 d . . . . .
C2 C 0.0924(11) 0.6275(3) 0.3247(9) 0.018(2) Uani 1 1 d . . . . .
C3 C -0.0689(13) 0.6315(4) 0.2953(11) 0.033(3) Uani 1 1 d . . . . .
H3A H -0.1434 0.6219 0.3463 0.040 Uiso 1 1 calc R U . . .
C4 C -0.0961(13) 0.6521(4) 0.1768(12) 0.039(3) Uani 1 1 d . . . . .
H4 H -0.1946 0.6612 0.1299 0.047 Uiso 1 1 calc R U . . .
C5 C 0.1266(14) 0.5864(5) 0.5477(11) 0.046(4) Uani 1 1 d . . . . .
H5A H 0.1410 0.6086 0.6203 0.069 Uiso 1 1 calc R U . . .
H5B H 0.1796 0.5564 0.5743 0.069 Uiso 1 1 calc R U . . .
H5C H 0.0151 0.5805 0.5197 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6328(13) 0.7118(4) 0.4058(11) 0.036(3) Uani 1 1 d . . . . .
C7 C 0.5460(13) 0.7373(4) 0.2961(10) 0.028(3) Uani 1 1 d . . . . .
C8 C 0.5507(15) 0.7856(4) 0.2580(13) 0.038(3) Uani 1 1 d . . . . .
H8 H 0.6173 0.8101 0.2972 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4401(16) 0.7885(4) 0.1546(13) 0.042(3) Uani 1 1 d . . . . .
H9A H 0.4119 0.8166 0.1061 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7588(16) 0.7354(5) 0.5000(12) 0.052(4) Uani 1 1 d . . . . .
H10A H 0.8066 0.7608 0.4565 0.079 Uiso 1 1 calc R U . . .
H10B H 0.8383 0.7119 0.5338 0.079 Uiso 1 1 calc R U . . .
H10C H 0.7136 0.7489 0.5710 0.079 Uiso 1 1 calc R U . . .
C11 C 0.6036(11) 0.5605(3) 0.1926(9) 0.019(2) Uani 1 1 d . . . . .
C12 C 0.5290(11) 0.5803(3) 0.0674(9) 0.019(2) Uani 1 1 d . . . . .
C13 C 0.5478(13) 0.5698(4) -0.0570(10) 0.029(2) Uani 1 1 d . . . . .
H13 H 0.6125 0.5462 -0.0848 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4506(13) 0.6018(4) -0.1320(10) 0.031(3) Uani 1 1 d . . . . .
H14 H 0.4344 0.6042 -0.2231 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7170(13) 0.5201(4) 0.2034(10) 0.028(3) Uani 1 1 d . . . . .
H15A H 0.7232 0.5080 0.1174 0.042 Uiso 1 1 calc R U . . .
H15B H 0.6821 0.4947 0.2553 0.042 Uiso 1 1 calc R U . . .
H15C H 0.8201 0.5313 0.2446 0.042 Uiso 1 1 calc R U . . .
B1 B 0.6061(13) 0.5931(4) 0.5210(10) 0.020(2) Uani 1 1 d D . . . .
C16 C 0.7039(14) 0.5636(4) 0.6447(10) 0.013(3) Uani 0.71(2) 1 d DG U P A 1
C17 C 0.8247(14) 0.5856(4) 0.7269(11) 0.023(4) Uani 0.71(2) 1 d G . P A 1
H17 H 0.8446 0.6185 0.7172 0.027 Uiso 0.71(2) 1 calc R U P A 1
C18 C 0.9162(11) 0.5595(5) 0.8232(9) 0.023(4) Uani 0.71(2) 1 d G U P A 1
H18 H 0.9987 0.5745 0.8793 0.028 Uiso 0.71(2) 1 calc R U P A 1
C19 C 0.8869(13) 0.5114(5) 0.8373(9) 0.024(3) Uani 0.71(2) 1 d G U P A 1
H19 H 0.9495 0.4936 0.9032 0.028 Uiso 0.71(2) 1 calc R U P A 1
C20 C 0.7661(15) 0.4894(4) 0.7552(11) 0.025(4) Uani 0.71(2) 1 d G . P A 1
H20 H 0.7461 0.4565 0.7648 0.029 Uiso 0.71(2) 1 calc R U P A 1
C21 C 0.6746(14) 0.5155(4) 0.6588(11) 0.020(3) Uani 0.71(2) 1 d G . P A 1
H21 H 0.5921 0.5004 0.6027 0.023 Uiso 0.71(2) 1 calc R U P A 1
C16' C 0.719(4) 0.5769(11) 0.651(3) 0.013(3) Uani 0.29(2) 1 d DG U P A 2
C17' C 0.830(4) 0.6035(10) 0.730(3) 0.023(4) Uani 0.29(2) 1 d G . P A 2
H17' H 0.8365 0.6368 0.7180 0.027 Uiso 0.29(2) 1 calc R U P A 2
C18' C 0.933(3) 0.5813(12) 0.828(2) 0.023(4) Uani 0.29(2) 1 d G U P A 2
H18' H 1.0090 0.5995 0.8820 0.028 Uiso 0.29(2) 1 calc R U P A 2
C19' C 0.924(3) 0.5325(12) 0.845(2) 0.024(3) Uani 0.29(2) 1 d G U P A 2
H19' H 0.9939 0.5173 0.9119 0.028 Uiso 0.29(2) 1 calc R U P A 2
C20' C 0.812(4) 0.5059(10) 0.766(3) 0.025(4) Uani 0.29(2) 1 d G . P A 2
H20' H 0.8062 0.4725 0.7779 0.029 Uiso 0.29(2) 1 calc R U P A 2
C21' C 0.710(4) 0.5281(11) 0.668(3) 0.020(3) Uani 0.29(2) 1 d G . P A 2
H21' H 0.6337 0.5099 0.6139 0.023 Uiso 0.29(2) 1 calc R U P A 2


_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 2.140(7) . ?
Co1 N2 2.143(8) . ?
Co1 N4 2.152(9) . ?
Co1 N5 2.143(9) . ?
Co1 N7 2.125(8) . ?
Co1 N8 2.188(8) . ?
O1 N1 1.388(10) . ?
O1 B1 1.480(13) . ?
O2 N4 1.377(11) . ?
O2 B1 1.497(14) . ?
O3 N7 1.374(10) . ?
O3 B1 1.494(12) . ?
N1 C1 1.268(12) . ?
N2 N3 1.338(12) . ?
N2 C2 1.336(12) . ?
N3 H3 0.9038 . ?
N3 C4 1.354(14) . ?
N4 C6 1.274(14) . ?
N5 N6 1.339(13) . ?
N5 C7 1.308(14) . ?
N6 H6 0.9481 . ?
N6 C9 1.340(15) . ?
N7 C11 1.288(12) . ?
N8 N9 1.346(11) . ?
N8 C12 1.336(12) . ?
N9 H9 0.9902 . ?
N9 C14 1.339(13) . ?
C1 C2 1.470(13) . ?
C1 C5 1.518(14) . ?
C2 C3 1.390(14) . ?
C3 H3A 0.9500 . ?
C3 C4 1.363(15) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.460(17) . ?
C6 C10 1.504(16) . ?
C7 C8 1.420(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.329(18) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.478(13) . ?
C11 C15 1.498(13) . ?
C12 C13 1.381(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(15) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
B1 C16 1.656(13) . ?
B1 C16' 1.608(18) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 H17 0.9500 . ?
C17 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C19 1.3900 . ?
C19 H19 0.9500 . ?
C19 C20 1.3900 . ?
C20 H20 0.9500 . ?
C20 C21 1.3900 . ?
C21 H21 0.9500 . ?
C16' C17' 1.3900 . ?
C16' C21' 1.3900 . ?
C17' H17' 0.9500 . ?
C17' C18' 1.3900 . ?
C18' H18' 0.9500 . ?
C18' C19' 1.3900 . ?
C19' H19' 0.9500 . ?
C19' C20' 1.3900 . ?
C20' H20' 0.9500 . ?
C20' C21' 1.3900 . ?
C21' H21' 0.9500 . ?

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 N2 74.2(3) . . ?
N1 Co1 N4 80.4(3) . . ?
N1 Co1 N5 129.8(3) . . ?
N1 Co1 N8 136.0(3) . . ?
N2 Co1 N4 135.6(3) . . ?
N2 Co1 N5 95.2(3) . . ?
N2 Co1 N8 94.5(3) . . ?
N4 Co1 N8 128.4(3) . . ?
N5 Co1 N4 74.0(3) . . ?
N5 Co1 N8 92.8(3) . . ?
N7 Co1 N1 81.5(3) . . ?
N7 Co1 N2 129.8(3) . . ?
N7 Co1 N4 80.0(3) . . ?
N7 Co1 N5 133.1(3) . . ?
N7 Co1 N8 73.7(3) . . ?
N1 O1 B1 114.3(7) . . ?
N4 O2 B1 113.7(7) . . ?
N7 O3 B1 115.0(7) . . ?
O1 N1 Co1 124.1(5) . . ?
C1 N1 Co1 119.7(7) . . ?
C1 N1 O1 116.2(7) . . ?
N3 N2 Co1 140.2(7) . . ?
C2 N2 Co1 115.3(6) . . ?
C2 N2 N3 104.4(8) . . ?
N2 N3 H3 134.7 . . ?
N2 N3 C4 111.9(9) . . ?
C4 N3 H3 110.9 . . ?
O2 N4 Co1 124.5(6) . . ?
C6 N4 Co1 119.0(8) . . ?
C6 N4 O2 116.4(9) . . ?
N6 N5 Co1 138.4(8) . . ?
C7 N5 Co1 115.2(7) . . ?
C7 N5 N6 106.3(9) . . ?
N5 N6 H6 135.2 . . ?
N5 N6 C9 110.1(11) . . ?
C9 N6 H6 113.0 . . ?
O3 N7 Co1 124.2(5) . . ?
C11 N7 Co1 120.8(7) . . ?
C11 N7 O3 115.0(8) . . ?
N9 N8 Co1 139.9(6) . . ?
C12 N8 Co1 115.4(6) . . ?
C12 N8 N9 104.4(8) . . ?
N8 N9 H9 131.6 . . ?
C14 N9 N8 112.2(8) . . ?
C14 N9 H9 116.2 . . ?
N1 C1 C2 114.0(8) . . ?
N1 C1 C5 125.5(9) . . ?
C2 C1 C5 120.5(9) . . ?
N2 C2 C1 116.6(8) . . ?
N2 C2 C3 111.9(9) . . ?
C3 C2 C1 131.5(9) . . ?
C2 C3 H3A 127.8 . . ?
C4 C3 C2 104.5(9) . . ?
C4 C3 H3A 127.8 . . ?
N3 C4 C3 107.2(10) . . ?
N3 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 113.4(10) . . ?
N4 C6 C10 124.7(12) . . ?
C7 C6 C10 121.9(11) . . ?
N5 C7 C6 118.3(10) . . ?
N5 C7 C8 110.4(11) . . ?
C8 C7 C6 131.3(11) . . ?
C7 C8 H8 128.1 . . ?
C9 C8 C7 103.9(11) . . ?
C9 C8 H8 128.1 . . ?
N6 C9 H9A 125.3 . . ?
C8 C9 N6 109.4(11) . . ?
C8 C9 H9A 125.3 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 113.9(8) . . ?
N7 C11 C15 123.6(9) . . ?
C12 C11 C15 122.5(8) . . ?
N8 C12 C11 116.1(8) . . ?
N8 C12 C13 112.2(9) . . ?
C13 C12 C11 131.6(9) . . ?
C12 C13 H13 127.9 . . ?
C12 C13 C14 104.2(9) . . ?
C14 C13 H13 127.9 . . ?
N9 C14 C13 107.0(9) . . ?
N9 C14 H14 126.5 . . ?
C13 C14 H14 126.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 B1 O2 112.0(8) . . ?
O1 B1 O3 112.6(8) . . ?
O1 B1 C16 107.0(8) . . ?
O1 B1 C16' 111.7(17) . . ?
O2 B1 C16 111.3(8) . . ?
O2 B1 C16' 97.7(14) . . ?
O3 B1 O2 110.4(8) . . ?
O3 B1 C16 103.1(9) . . ?
O3 B1 C16' 111.6(16) . . ?
C17 C16 B1 120.1(7) . . ?
C17 C16 C21 120.0 . . ?
C21 C16 B1 119.6(7) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C17' C16' B1 128.6(18) . . ?
C17' C16' C21' 120.0 . . ?
C21' C16' B1 110.8(18) . . ?
C16' C17' H17' 120.0 . . ?
C18' C17' C16' 120.0 . . ?
C18' C17' H17' 120.0 . . ?
C17' C18' H18' 120.0 . . ?
C17' C18' C19' 120.0 . . ?
C19' C18' H18' 120.0 . . ?
C18' C19' H19' 120.0 . . ?
C18' C19' C20' 120.0 . . ?
C20' C19' H19' 120.0 . . ?
C19' C20' H20' 120.0 . . ?
C19' C20' C21' 120.0 . . ?
C21' C20' H20' 120.0 . . ?
C16' C21' H21' 120.0 . . ?
C20' C21' C16' 120.0 . . ?
C20' C21' H21' 120.0 . . ?

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 C1 C2 -1.8(11) . . . . ?
Co1 N1 C1 C5 178.9(9) . . . . ?
Co1 N2 N3 C4 -174.7(9) . . . . ?
Co1 N2 C2 C1 -4.9(11) . . . . ?
Co1 N2 C2 C3 177.9(7) . . . . ?
Co1 N4 C6 C7 1.1(12) . . . . ?
Co1 N4 C6 C10 -178.8(9) . . . . ?
Co1 N5 N6 C9 175.6(8) . . . . ?
Co1 N5 C7 C6 0.8(11) . . . . ?
Co1 N5 C7 C8 -177.5(6) . . . . ?
Co1 N7 C11 C12 -1.6(11) . . . . ?
Co1 N7 C11 C15 177.0(8) . . . . ?
Co1 N8 N9 C14 172.3(8) . . . . ?
Co1 N8 C12 C11 3.0(11) . . . . ?
Co1 N8 C12 C13 -173.8(7) . . . . ?
O1 N1 C1 C2 178.8(7) . . . . ?
O1 N1 C1 C5 -0.5(14) . . . . ?
O1 B1 C16 C17 -121.1(9) . . . . ?
O1 B1 C16 C21 65.0(11) . . . . ?
O1 B1 C16' C17' -114(2) . . . . ?
O1 B1 C16' C21' 75(2) . . . . ?
O2 N4 C6 C7 179.6(8) . . . . ?
O2 N4 C6 C10 -0.3(15) . . . . ?
O2 B1 C16 C17 1.6(12) . . . . ?
O2 B1 C16 C21 -172.3(8) . . . . ?
O2 B1 C16' C17' 4(3) . . . . ?
O2 B1 C16' C21' -167.2(17) . . . . ?
O3 N7 C11 C12 -179.7(7) . . . . ?
O3 N7 C11 C15 -1.1(14) . . . . ?
O3 B1 C16 C17 120.0(9) . . . . ?
O3 B1 C16 C21 -53.9(11) . . . . ?
O3 B1 C16' C17' 119(2) . . . . ?
O3 B1 C16' C21' -52(2) . . . . ?
N1 O1 B1 O2 66.6(10) . . . . ?
N1 O1 B1 O3 -58.5(11) . . . . ?
N1 O1 B1 C16 -171.1(8) . . . . ?
N1 O1 B1 C16' 175.0(14) . . . . ?
N1 C1 C2 N2 4.5(13) . . . . ?
N1 C1 C2 C3 -179.0(11) . . . . ?
N2 N3 C4 C3 -3.0(14) . . . . ?
N2 C2 C3 C4 -2.3(13) . . . . ?
N3 N2 C2 C1 177.8(9) . . . . ?
N3 N2 C2 C3 0.6(12) . . . . ?
N4 O2 B1 O1 -59.8(10) . . . . ?
N4 O2 B1 O3 66.5(10) . . . . ?
N4 O2 B1 C16 -179.6(8) . . . . ?
N4 O2 B1 C16' -177.0(17) . . . . ?
N4 C6 C7 N5 -1.3(14) . . . . ?
N4 C6 C7 C8 176.6(10) . . . . ?
N5 N6 C9 C8 0.6(13) . . . . ?
N5 C7 C8 C9 1.2(12) . . . . ?
N6 N5 C7 C6 177.5(9) . . . . ?
N6 N5 C7 C8 -0.8(11) . . . . ?
N7 O3 B1 O1 65.9(10) . . . . ?
N7 O3 B1 O2 -60.1(10) . . . . ?
N7 O3 B1 C16 -179.1(8) . . . . ?
N7 O3 B1 C16' -167.6(15) . . . . ?
N7 C11 C12 N8 -1.0(13) . . . . ?
N7 C11 C12 C13 175.0(11) . . . . ?
N8 N9 C14 C13 0.1(13) . . . . ?
N8 C12 C13 C14 -1.3(12) . . . . ?
N9 N8 C12 C11 178.1(8) . . . . ?
N9 N8 C12 C13 1.4(11) . . . . ?
C1 C2 C3 C4 -179.0(11) . . . . ?
C2 N2 N3 C4 1.5(12) . . . . ?
C2 C3 C4 N3 3.1(14) . . . . ?
C5 C1 C2 N2 -176.2(10) . . . . ?
C5 C1 C2 C3 0.3(17) . . . . ?
C6 C7 C8 C9 -176.9(11) . . . . ?
C7 N5 N6 C9 0.2(11) . . . . ?
C7 C8 C9 N6 -1.0(12) . . . . ?
C10 C6 C7 N5 178.6(10) . . . . ?
C10 C6 C7 C8 -3.5(17) . . . . ?
C11 C12 C13 C14 -177.4(10) . . . . ?
C12 N8 N9 C14 -0.9(11) . . . . ?
C12 C13 C14 N9 0.7(12) . . . . ?
C15 C11 C12 N8 -179.6(9) . . . . ?
C15 C11 C12 C13 -3.6(17) . . . . ?
B1 O1 N1 Co1 -5.5(10) . . . . ?
B1 O1 N1 C1 173.9(8) . . . . ?
B1 O2 N4 Co1 -6.2(10) . . . . ?
B1 O2 N4 C6 175.4(8) . . . . ?
B1 O3 N7 Co1 -6.4(10) . . . . ?
B1 O3 N7 C11 171.6(8) . . . . ?
B1 C16 C17 C18 -173.9(12) . . . . ?
B1 C16 C21 C20 173.9(12) . . . . ?
B1 C16' C17' C18' -170(3) . . . . ?
B1 C16' C21' C20' 172(3) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C16' C17' C18' C19' 0.0 . . . . ?
C17' C16' C21' C20' 0.0 . . . . ?
C17' C18' C19' C20' 0.0 . . . . ?
C18' C19' C20' C21' 0.0 . . . . ?
C19' C20' C21' C16' 0.0 . . . . ?
C21' C16' C17' C18' 0.0 . . . . ?

_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_ab379
_database_code_depnum_ccdc_archive 'CCDC 2286466'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 B Co N9 O3, Cl'
_chemical_formula_sum            'C21 H23 B Cl Co N9 O3'
_chemical_formula_weight         554.67
_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 0.0050 0.0020 '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'
B B 0.0020 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1780 0.2030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3500 1.2030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0080 '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                   15.744(3)
_cell_length_b                   8.1571(16)
_cell_length_c                   18.785(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.17(3)
_cell_angle_gamma                90
_cell_volume                     2402.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    100
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    1.215
_exptl_absorpt_correction_T_max  0.0511
_exptl_absorpt_correction_T_min  0.0162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13505
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        28.782
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         3.178
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.80246
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4082
_reflns_number_total             4385
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0128(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.063
_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)+(0.0486P)²+2.2443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N9(H9), C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_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 0.28264(2) 0.44815(4) 0.52940(2) 0.02099(15) Uani 1 1 d . . . . .
O1 O 0.25707(12) 0.5414(2) 0.36753(9) 0.0263(4) Uani 1 1 d . . . . .
O2 O 0.12307(12) 0.5458(2) 0.42499(9) 0.0254(4) Uani 1 1 d . . . . .
O3 O 0.18798(12) 0.2809(2) 0.39699(9) 0.0285(4) Uani 1 1 d . . . . .
N1 N 0.30915(14) 0.5571(2) 0.43037(11) 0.0241(5) Uani 1 1 d . . . . .
N2 N 0.40229(14) 0.5781(2) 0.55088(11) 0.0239(5) Uani 1 1 d . . . . .
N3 N 0.45910(14) 0.6175(3) 0.60616(11) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.4573 0.5796 0.6499 0.032 Uiso 1 1 calc R U . . .
N4 N 0.15940(14) 0.5519(2) 0.49438(11) 0.0231(5) Uani 1 1 d . . . . .
N5 N 0.23548(14) 0.5530(2) 0.62195(11) 0.0240(5) Uani 1 1 d . . . . .
N6 N 0.26305(15) 0.5828(3) 0.69079(11) 0.0271(5) Uani 1 1 d . . . . .
H6 H 0.3116 0.5466 0.7120 0.033 Uiso 1 1 calc R U . . .
N7 N 0.23321(14) 0.2569(3) 0.46194(11) 0.0246(5) Uani 1 1 d . . . . .
N8 N 0.31930(13) 0.2246(3) 0.58459(10) 0.0233(4) Uani 1 1 d . . . . .
N9 N 0.36124(14) 0.1725(3) 0.64577(11) 0.0258(5) Uani 1 1 d . . . . .
H9 H 0.3863 0.2380 0.6785 0.031 Uiso 1 1 calc R U . . .
C1 C 0.37533(16) 0.6469(3) 0.42687(13) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.42721(16) 0.6615(3) 0.49481(13) 0.0228(5) Uani 1 1 d . . . . .
C3 C 0.50063(17) 0.7537(3) 0.51460(14) 0.0283(6) Uani 1 1 d . . . . .
H3A H 0.5311 0.8230 0.4852 0.034 Uiso 1 1 calc R U . . .
C4 C 0.51869(17) 0.7213(3) 0.58655(14) 0.0298(6) Uani 1 1 d . . . . .
H4 H 0.5650 0.7648 0.6167 0.036 Uiso 1 1 calc R U . . .
C5 C 0.39903(18) 0.7340(4) 0.36175(14) 0.0315(6) Uani 1 1 d . . . . .
H5A H 0.3780 0.6719 0.3191 0.047 Uiso 1 1 calc R U . . .
H5B H 0.4612 0.7437 0.3636 0.047 Uiso 1 1 calc R U . . .
H5C H 0.3735 0.8436 0.3598 0.047 Uiso 1 1 calc R U . . .
C6 C 0.11601(16) 0.6259(3) 0.53970(13) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.16022(16) 0.6300(3) 0.61124(13) 0.0232(5) Uani 1 1 d . . . . .
C8 C 0.13968(18) 0.7086(3) 0.67368(13) 0.0290(6) Uani 1 1 d . . . . .
H8 H 0.0902 0.7713 0.6804 0.035 Uiso 1 1 calc R U . . .
C9 C 0.20678(18) 0.6750(3) 0.72293(14) 0.0304(6) Uani 1 1 d . . . . .
H9A H 0.2126 0.7105 0.7713 0.036 Uiso 1 1 calc R U . . .
C10 C 0.03165(17) 0.7068(3) 0.52415(14) 0.0287(6) Uani 1 1 d . . . . .
H10A H 0.0384 0.8258 0.5293 0.043 Uiso 1 1 calc R U . . .
H10B H -0.0078 0.6670 0.5578 0.043 Uiso 1 1 calc R U . . .
H10C H 0.0088 0.6808 0.4752 0.043 Uiso 1 1 calc R U . . .
C11 C 0.24261(17) 0.1063(3) 0.48081(13) 0.0242(5) Uani 1 1 d . . . . .
C12 C 0.29116(16) 0.0871(3) 0.55051(14) 0.0225(5) Uani 1 1 d . . . . .
C13 C 0.31560(18) -0.0517(3) 0.59083(15) 0.0281(6) Uani 1 1 d . . . . .
H13 H 0.3038 -0.1632 0.5791 0.034 Uiso 1 1 calc R U . . .
C14 C 0.36028(18) 0.0085(3) 0.65099(15) 0.0304(6) Uani 1 1 d . . . . .
H14 H 0.3861 -0.0545 0.6896 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2080(2) -0.0347(3) 0.43732(16) 0.0334(6) Uani 1 1 d . . . . .
H15A H 0.1456 -0.0306 0.4331 0.050 Uiso 1 1 calc R U . . .
H15B H 0.2273 -0.1374 0.4606 0.050 Uiso 1 1 calc R U . . .
H15C H 0.2284 -0.0292 0.3896 0.050 Uiso 1 1 calc R U . . .
C16 C 0.12272(17) 0.4466(3) 0.29777(13) 0.0241(5) Uani 1 1 d . . . . .
C17 C 0.04023(17) 0.5081(3) 0.28398(13) 0.0259(5) Uani 1 1 d . . . . .
H17 H 0.0144 0.5632 0.3210 0.031 Uiso 1 1 calc R U . . .
C18 C -0.00522(18) 0.4907(3) 0.21714(14) 0.0289(6) Uani 1 1 d . . . . .
H18 H -0.0612 0.5344 0.2088 0.035 Uiso 1 1 calc R U . . .
C19 C 0.03165(19) 0.4095(3) 0.16301(14) 0.0313(6) Uani 1 1 d . . . . .
H19 H 0.0008 0.3966 0.1175 0.038 Uiso 1 1 calc R U . . .
C20 C 0.11344(19) 0.3469(3) 0.17509(14) 0.0314(6) Uani 1 1 d . . . . .
H20 H 0.1387 0.2912 0.1379 0.038 Uiso 1 1 calc R U . . .
C21 C 0.15859(18) 0.3657(3) 0.24164(13) 0.0284(6) Uani 1 1 d . . . . .
H21 H 0.2148 0.3231 0.2493 0.034 Uiso 1 1 calc R U . . .
B1 B 0.17445(19) 0.4555(3) 0.37506(15) 0.0232(6) Uani 1 1 d . . . . .
Cl1 Cl 0.43796(4) 0.43677(8) 0.75086(3) 0.02943(19) 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
Co1 N1 2.137(2) . ?
Co1 N2 2.168(2) . ?
Co1 N4 2.164(2) . ?
Co1 N5 2.130(2) . ?
Co1 N7 2.114(2) . ?
Co1 N8 2.151(2) . ?
O1 N1 1.381(3) . ?
O1 B1 1.495(3) . ?
O2 N4 1.376(3) . ?
O2 B1 1.488(3) . ?
O3 N7 1.370(3) . ?
O3 B1 1.493(3) . ?
N1 C1 1.280(3) . ?
N2 N3 1.347(3) . ?
N2 C2 1.341(3) . ?
N3 H3 0.8800 . ?
N3 C4 1.340(4) . ?
N4 C6 1.289(3) . ?
N5 N6 1.349(3) . ?
N5 C7 1.340(3) . ?
N6 H6 0.8800 . ?
N6 C9 1.346(4) . ?
N7 C11 1.284(3) . ?
N8 N9 1.342(3) . ?
N8 C12 1.346(3) . ?
N9 H9 0.8800 . ?
N9 C14 1.342(4) . ?
C1 C2 1.457(3) . ?
C1 C5 1.491(3) . ?
C2 C3 1.401(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.457(3) . ?
C6 C10 1.488(4) . ?
C7 C8 1.400(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.464(3) . ?
C11 C15 1.486(3) . ?
C12 C13 1.397(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.395(4) . ?
C16 C21 1.405(4) . ?
C16 B1 1.601(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(4) . ?
C21 H21 0.9500 . ?

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 N2 73.97(8) . . ?
N1 Co1 N4 79.21(8) . . ?
N1 Co1 N8 135.02(8) . . ?
N4 Co1 N2 127.28(8) . . ?
N5 Co1 N1 130.80(8) . . ?
N5 Co1 N2 90.73(8) . . ?
N5 Co1 N4 73.87(8) . . ?
N5 Co1 N8 92.59(8) . . ?
N7 Co1 N1 82.83(8) . . ?
N7 Co1 N2 137.69(9) . . ?
N7 Co1 N4 80.48(8) . . ?
N7 Co1 N5 130.47(9) . . ?
N7 Co1 N8 74.42(8) . . ?
N8 Co1 N2 97.71(8) . . ?
N8 Co1 N4 132.25(8) . . ?
N1 O1 B1 114.67(19) . . ?
N4 O2 B1 114.31(19) . . ?
N7 O3 B1 115.59(18) . . ?
O1 N1 Co1 123.90(15) . . ?
C1 N1 Co1 120.43(17) . . ?
C1 N1 O1 115.6(2) . . ?
N3 N2 Co1 139.97(17) . . ?
C2 N2 Co1 114.36(16) . . ?
C2 N2 N3 105.3(2) . . ?
N2 N3 H3 124.1 . . ?
C4 N3 N2 111.8(2) . . ?
C4 N3 H3 124.1 . . ?
O2 N4 Co1 123.96(15) . . ?
C6 N4 Co1 119.77(17) . . ?
C6 N4 O2 116.3(2) . . ?
N6 N5 Co1 138.52(17) . . ?
C7 N5 Co1 115.73(16) . . ?
C7 N5 N6 105.3(2) . . ?
N5 N6 H6 124.4 . . ?
C9 N6 N5 111.3(2) . . ?
C9 N6 H6 124.4 . . ?
O3 N7 Co1 124.20(15) . . ?
C11 N7 Co1 120.92(17) . . ?
C11 N7 O3 114.9(2) . . ?
N9 N8 Co1 140.44(16) . . ?
N9 N8 C12 105.0(2) . . ?
C12 N8 Co1 114.50(16) . . ?
N8 N9 H9 124.1 . . ?
C14 N9 N8 111.7(2) . . ?
C14 N9 H9 124.1 . . ?
N1 C1 C2 113.4(2) . . ?
N1 C1 C5 125.4(2) . . ?
C2 C1 C5 121.2(2) . . ?
N2 C2 C1 117.8(2) . . ?
N2 C2 C3 110.9(2) . . ?
C3 C2 C1 131.3(2) . . ?
C2 C3 H3A 127.8 . . ?
C4 C3 C2 104.4(2) . . ?
C4 C3 H3A 127.8 . . ?
N3 C4 C3 107.6(2) . . ?
N3 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 112.5(2) . . ?
N4 C6 C10 126.5(2) . . ?
C7 C6 C10 121.0(2) . . ?
N5 C7 C6 118.1(2) . . ?
N5 C7 C8 110.9(2) . . ?
C8 C7 C6 131.0(2) . . ?
C7 C8 H8 127.7 . . ?
C9 C8 C7 104.6(2) . . ?
C9 C8 H8 127.7 . . ?
N6 C9 C8 107.9(2) . . ?
N6 C9 H9A 126.0 . . ?
C8 C9 H9A 126.0 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 112.8(2) . . ?
N7 C11 C15 124.2(2) . . ?
C12 C11 C15 123.0(2) . . ?
N8 C12 C11 117.3(2) . . ?
N8 C12 C13 110.8(2) . . ?
C13 C12 C11 131.9(2) . . ?
C12 C13 H13 127.7 . . ?
C14 C13 C12 104.6(2) . . ?
C14 C13 H13 127.7 . . ?
N9 C14 C13 107.8(2) . . ?
N9 C14 H14 126.1 . . ?
C13 C14 H14 126.1 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.4(2) . . ?
C17 C16 B1 122.7(2) . . ?
C21 C16 B1 119.7(2) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.3(3) . . ?
C20 C21 H21 119.4 . . ?
O1 B1 C16 108.1(2) . . ?
O2 B1 O1 110.8(2) . . ?
O2 B1 O3 111.8(2) . . ?
O2 B1 C16 109.5(2) . . ?
O3 B1 O1 111.7(2) . . ?
O3 B1 C16 104.76(19) . . ?

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 C1 C2 0.8(3) . . . . ?
Co1 N1 C1 C5 -177.8(2) . . . . ?
Co1 N2 N3 C4 -172.3(2) . . . . ?
Co1 N2 C2 C1 -3.7(3) . . . . ?
Co1 N2 C2 C3 174.63(17) . . . . ?
Co1 N4 C6 C7 0.9(3) . . . . ?
Co1 N4 C6 C10 178.5(2) . . . . ?
Co1 N5 N6 C9 171.6(2) . . . . ?
Co1 N5 C7 C6 3.7(3) . . . . ?
Co1 N5 C7 C8 -173.76(17) . . . . ?
Co1 N7 C11 C12 -1.3(3) . . . . ?
Co1 N7 C11 C15 178.4(2) . . . . ?
Co1 N8 N9 C14 177.7(2) . . . . ?
Co1 N8 C12 C11 1.8(3) . . . . ?
Co1 N8 C12 C13 -178.28(18) . . . . ?
O1 N1 C1 C2 179.06(19) . . . . ?
O1 N1 C1 C5 0.5(4) . . . . ?
O2 N4 C6 C7 -178.55(19) . . . . ?
O2 N4 C6 C10 -0.9(4) . . . . ?
O3 N7 C11 C12 -179.9(2) . . . . ?
O3 N7 C11 C15 -0.1(4) . . . . ?
N1 O1 B1 O2 60.5(3) . . . . ?
N1 O1 B1 O3 -64.8(3) . . . . ?
N1 O1 B1 C16 -179.52(19) . . . . ?
N1 C1 C2 N2 2.0(3) . . . . ?
N1 C1 C2 C3 -175.9(3) . . . . ?
N2 N3 C4 C3 0.3(3) . . . . ?
N2 C2 C3 C4 -0.1(3) . . . . ?
N3 N2 C2 C1 -178.0(2) . . . . ?
N3 N2 C2 C3 0.3(3) . . . . ?
N4 O2 B1 O1 -64.7(3) . . . . ?
N4 O2 B1 O3 60.5(3) . . . . ?
N4 O2 B1 C16 176.13(18) . . . . ?
N4 C6 C7 N5 -3.0(3) . . . . ?
N4 C6 C7 C8 173.9(3) . . . . ?
N5 N6 C9 C8 -0.4(3) . . . . ?
N5 C7 C8 C9 0.0(3) . . . . ?
N6 N5 C7 C6 177.3(2) . . . . ?
N6 N5 C7 C8 -0.2(3) . . . . ?
N7 O3 B1 O1 61.9(3) . . . . ?
N7 O3 B1 O2 -62.9(3) . . . . ?
N7 O3 B1 C16 178.7(2) . . . . ?
N7 C11 C12 N8 -0.4(4) . . . . ?
N7 C11 C12 C13 179.7(3) . . . . ?
N8 N9 C14 C13 -0.2(3) . . . . ?
N8 C12 C13 C14 -0.2(3) . . . . ?
N9 N8 C12 C11 -179.8(2) . . . . ?
N9 N8 C12 C13 0.1(3) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C2 N2 N3 C4 -0.4(3) . . . . ?
C2 C3 C4 N3 -0.1(3) . . . . ?
C5 C1 C2 N2 -179.3(2) . . . . ?
C5 C1 C2 C3 2.7(4) . . . . ?
C6 C7 C8 C9 -177.1(3) . . . . ?
C7 N5 N6 C9 0.4(3) . . . . ?
C7 C8 C9 N6 0.2(3) . . . . ?
C10 C6 C7 N5 179.2(2) . . . . ?
C10 C6 C7 C8 -3.9(4) . . . . ?
C11 C12 C13 C14 179.6(3) . . . . ?
C12 N8 N9 C14 0.0(3) . . . . ?
C12 C13 C14 N9 0.2(3) . . . . ?
C15 C11 C12 N8 179.8(3) . . . . ?
C15 C11 C12 C13 0.0(5) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C16 C21 C20 -0.4(4) . . . . ?
C17 C16 B1 O1 -124.2(3) . . . . ?
C17 C16 B1 O2 -3.4(3) . . . . ?
C17 C16 B1 O3 116.6(3) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C16 0.4(4) . . . . ?
C21 C16 C17 C18 -0.1(4) . . . . ?
C21 C16 B1 O1 59.6(3) . . . . ?
C21 C16 B1 O2 -179.6(2) . . . . ?
C21 C16 B1 O3 -59.6(3) . . . . ?
B1 O1 N1 Co1 6.2(3) . . . . ?
B1 O1 N1 C1 -172.0(2) . . . . ?
B1 O2 N4 Co1 2.1(3) . . . . ?
B1 O2 N4 C6 -178.5(2) . . . . ?
B1 O3 N7 Co1 -0.1(3) . . . . ?
B1 O3 N7 C11 178.4(2) . . . . ?
B1 C16 C17 C18 -176.4(2) . . . . ?
B1 C16 C21 C20 176.1(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_sv127_b
_database_code_depnum_ccdc_archive 'CCDC 2289263'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-17 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-08-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Br, C21 H23 B Co N9 O3, C6 H6'
_chemical_formula_sum            'C27 H29 B Br Co N9 O3'
_chemical_formula_weight         677.24
_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 0.0080 0.0030 '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'
B B 0.0040 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -2.5840 0.5840 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.2490 1.6810 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0230 0.0120 '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                   8.2500(16)
_cell_length_b                   13.319(3)
_cell_length_c                   14.251(3)
_cell_angle_alpha                89.48(3)
_cell_angle_beta                 74.35(3)
_cell_angle_gamma                76.82(3)
_cell_volume                     1465.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.1055
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25384
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.428
_diffrn_reflns_theta_min         3.614
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.9699
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4601
_reflns_number_total             6045
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.076
_refine_diff_density_min         -1.383
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.081
_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)+(0.0829P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1766
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N9(H9), C3(H3A), C4(H4), C8(H8), C9(H9A), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C1S(H1S), C2S(H2S), C3S(H3S),
  C4S(H4S), C5S(H5S), C6S(H6S)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_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
Br1 Br 0.67576(5) 0.08773(3) -0.03790(3) 0.02354(19) Uani 1 1 d . . . . .
Co1 Co 0.48733(6) 0.38288(4) 0.19895(4) 0.01504(19) Uani 1 1 d . . . . .
O1 O 0.2966(3) 0.61296(19) 0.26645(19) 0.0201(6) Uani 1 1 d . . . . .
O2 O 0.2902(3) 0.49868(18) 0.40416(19) 0.0182(6) Uani 1 1 d . . . . .
O3 O 0.5608(3) 0.55110(18) 0.32385(19) 0.0175(6) Uani 1 1 d . . . . .
N1 N 0.3321(4) 0.5350(2) 0.1950(2) 0.0177(7) Uani 1 1 d . . . . .
N2 N 0.4083(4) 0.3839(2) 0.0647(2) 0.0192(7) Uani 1 1 d . . . . .
N3 N 0.4235(4) 0.3206(2) -0.0125(2) 0.0197(7) Uani 1 1 d . . . . .
H3 H 0.4896 0.2575 -0.0237 0.024 Uiso 1 1 calc R U . . .
N4 N 0.3253(4) 0.4075(2) 0.3478(2) 0.0158(7) Uani 1 1 d . . . . .
N5 N 0.4063(4) 0.2394(2) 0.2369(2) 0.0170(7) Uani 1 1 d . . . . .
N6 N 0.4188(4) 0.1464(2) 0.1939(2) 0.0195(7) Uani 1 1 d . . . . .
H6 H 0.4807 0.1257 0.1339 0.023 Uiso 1 1 calc R U . . .
N7 N 0.6317(4) 0.4626(2) 0.2629(2) 0.0167(7) Uani 1 1 d . . . . .
N8 N 0.7536(4) 0.2960(2) 0.1480(2) 0.0184(7) Uani 1 1 d . . . . .
N9 N 0.8493(4) 0.2081(2) 0.0953(2) 0.0185(7) Uani 1 1 d . . . . .
H9 H 0.8076 0.1686 0.0633 0.022 Uiso 1 1 calc R U . . .
C1 C 0.2528(4) 0.5580(3) 0.1276(3) 0.0170(8) Uani 1 1 d . . . . .
C2 C 0.2953(4) 0.4720(3) 0.0546(3) 0.0176(8) Uani 1 1 d . . . . .
C3 C 0.2397(5) 0.4642(3) -0.0287(3) 0.0198(8) Uani 1 1 d . . . . .
H3A H 0.1608 0.5149 -0.0520 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3251(5) 0.3657(3) -0.0701(3) 0.0233(9) Uani 1 1 d . . . . .
H4 H 0.3160 0.3357 -0.1281 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1308(5) 0.6585(3) 0.1253(3) 0.0233(9) Uani 1 1 d . . . . .
H5A H 0.0411 0.6733 0.1878 0.035 Uiso 1 1 calc R U . . .
H5B H 0.0767 0.6550 0.0725 0.035 Uiso 1 1 calc R U . . .
H5C H 0.1942 0.7134 0.1142 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2573(4) 0.3354(3) 0.3911(3) 0.0179(8) Uani 1 1 d . . . . .
C7 C 0.2992(4) 0.2411(3) 0.3273(3) 0.0166(8) Uani 1 1 d . . . . .
C8 C 0.2447(5) 0.1483(3) 0.3414(3) 0.0254(10) Uani 1 1 d . . . . .
H8 H 0.1691 0.1298 0.3984 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3241(5) 0.0896(3) 0.2551(3) 0.0266(10) Uani 1 1 d . . . . .
H9A H 0.3141 0.0220 0.2411 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1474(5) 0.3439(3) 0.4942(3) 0.0255(10) Uani 1 1 d . . . . .
H10A H 0.2175 0.3500 0.5385 0.038 Uiso 1 1 calc R U . . .
H10B H 0.1013 0.2820 0.5078 0.038 Uiso 1 1 calc R U . . .
H10C H 0.0514 0.4051 0.5039 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7962(4) 0.4259(3) 0.2507(3) 0.0169(8) Uani 1 1 d . . . . .
C12 C 0.8654(4) 0.3320(3) 0.1857(3) 0.0182(8) Uani 1 1 d . . . . .
C13 C 1.0322(5) 0.2676(3) 0.1547(3) 0.0216(9) Uani 1 1 d . . . . .
H13 H 1.1339 0.2763 0.1694 0.026 Uiso 1 1 calc R U . . .
C14 C 1.0164(5) 0.1879(3) 0.0976(3) 0.0227(9) Uani 1 1 d . . . . .
H14 H 1.1060 0.1304 0.0662 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9042(5) 0.4729(3) 0.2987(3) 0.0226(9) Uani 1 1 d . . . . .
H15A H 0.8870 0.5467 0.2867 0.034 Uiso 1 1 calc R U . . .
H15B H 1.0266 0.4386 0.2716 0.034 Uiso 1 1 calc R U . . .
H15C H 0.8696 0.4643 0.3691 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3124(4) 0.6831(3) 0.4253(3) 0.0152(8) Uani 1 1 d . . . . .
C17 C 0.3557(5) 0.6777(3) 0.5143(3) 0.0217(9) Uani 1 1 d . . . . .
H17 H 0.4134 0.6133 0.5320 0.026 Uiso 1 1 calc R U . . .
C18 C 0.3156(5) 0.7655(3) 0.5777(3) 0.0237(9) Uani 1 1 d . . . . .
H18 H 0.3455 0.7599 0.6377 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2317(5) 0.8610(3) 0.5523(3) 0.0276(10) Uani 1 1 d . . . . .
H19 H 0.2050 0.9207 0.5947 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1877(5) 0.8681(3) 0.4646(3) 0.0271(10) Uani 1 1 d . . . . .
H20 H 0.1307 0.9329 0.4470 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2269(5) 0.7802(3) 0.4021(3) 0.0225(9) Uani 1 1 d . . . . .
H21 H 0.1951 0.7862 0.3426 0.027 Uiso 1 1 calc R U . . .
B1 B 0.3665(5) 0.5816(3) 0.3517(3) 0.0173(9) Uani 1 1 d . . . . .
C1S C 0.8447(5) -0.0768(3) 0.1663(3) 0.0252(10) Uani 1 1 d . . . . .
H1S H 0.9065 -0.0474 0.1110 0.030 Uiso 1 1 calc R U . . .
C2S C 0.6970(5) -0.1095(3) 0.1631(3) 0.0268(10) Uani 1 1 d . . . . .
H2S H 0.6576 -0.1020 0.1060 0.032 Uiso 1 1 calc R U . . .
C3S C 0.6073(5) -0.1535(3) 0.2444(3) 0.0285(10) Uani 1 1 d . . . . .
H3S H 0.5088 -0.1778 0.2419 0.034 Uiso 1 1 calc R U . . .
C4S C 0.6620(5) -0.1617(3) 0.3291(3) 0.0284(10) Uani 1 1 d . . . . .
H4S H 0.5988 -0.1896 0.3850 0.034 Uiso 1 1 calc R U . . .
C5S C 0.8091(5) -0.1292(3) 0.3313(3) 0.0299(10) Uani 1 1 d . . . . .
H5S H 0.8477 -0.1356 0.3887 0.036 Uiso 1 1 calc R U . . .
C6S C 0.9011(5) -0.0869(3) 0.2493(3) 0.0280(10) Uani 1 1 d . . . . .
H6S H 1.0023 -0.0651 0.2510 0.034 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 2.146(3) . ?
Co1 N2 2.181(4) . ?
Co1 N4 2.163(3) . ?
Co1 N5 2.181(3) . ?
Co1 N7 2.135(3) . ?
Co1 N8 2.165(3) . ?
O1 N1 1.386(4) . ?
O1 B1 1.497(5) . ?
O2 N4 1.391(4) . ?
O2 B1 1.491(5) . ?
O3 N7 1.385(4) . ?
O3 B1 1.502(5) . ?
N1 C1 1.299(5) . ?
N2 N3 1.352(5) . ?
N2 C2 1.356(5) . ?
N3 H3 0.8800 . ?
N3 C4 1.350(5) . ?
N4 C6 1.291(5) . ?
N5 N6 1.357(4) . ?
N5 C7 1.348(5) . ?
N6 H6 0.8800 . ?
N6 C9 1.354(5) . ?
N7 C11 1.297(5) . ?
N8 N9 1.354(4) . ?
N8 C12 1.357(5) . ?
N9 H9 0.8800 . ?
N9 C14 1.353(5) . ?
C1 C2 1.469(5) . ?
C1 C5 1.486(5) . ?
C2 C3 1.397(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.391(5) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.475(5) . ?
C6 C10 1.493(5) . ?
C7 C8 1.404(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(6) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.470(5) . ?
C11 C15 1.498(5) . ?
C12 C13 1.402(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.404(6) . ?
C16 C21 1.408(5) . ?
C16 B1 1.620(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.398(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.400(6) . ?
C21 H21 0.9500 . ?
C1S H1S 0.9500 . ?
C1S C2S 1.396(6) . ?
C1S C6S 1.379(6) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.399(6) . ?
C3S H3S 0.9500 . ?
C3S C4S 1.393(6) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.387(6) . ?
C5S H5S 0.9500 . ?
C5S C6S 1.402(6) . ?
C6S H6S 0.9500 . ?

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 N2 73.86(12) . . ?
N1 Co1 N4 79.19(12) . . ?
N1 Co1 N5 129.29(11) . . ?
N1 Co1 N8 140.02(12) . . ?
N4 Co1 N2 128.32(11) . . ?
N4 Co1 N5 73.58(11) . . ?
N4 Co1 N8 127.42(13) . . ?
N5 Co1 N2 90.72(12) . . ?
N7 Co1 N1 83.76(12) . . ?
N7 Co1 N2 137.92(12) . . ?
N7 Co1 N4 79.62(12) . . ?
N7 Co1 N5 130.31(12) . . ?
N7 Co1 N8 74.50(12) . . ?
N8 Co1 N2 100.57(12) . . ?
N8 Co1 N5 89.67(11) . . ?
N1 O1 B1 114.8(3) . . ?
N4 O2 B1 114.3(3) . . ?
N7 O3 B1 114.0(3) . . ?
O1 N1 Co1 123.8(2) . . ?
C1 N1 Co1 121.2(2) . . ?
C1 N1 O1 114.8(3) . . ?
N3 N2 Co1 140.6(2) . . ?
N3 N2 C2 105.0(3) . . ?
C2 N2 Co1 114.1(3) . . ?
N2 N3 H3 124.0 . . ?
C4 N3 N2 111.9(3) . . ?
C4 N3 H3 124.0 . . ?
O2 N4 Co1 123.7(2) . . ?
C6 N4 Co1 120.9(2) . . ?
C6 N4 O2 115.4(3) . . ?
N6 N5 Co1 139.2(2) . . ?
C7 N5 Co1 115.0(2) . . ?
C7 N5 N6 105.5(3) . . ?
N5 N6 H6 124.2 . . ?
C9 N6 N5 111.5(3) . . ?
C9 N6 H6 124.2 . . ?
O3 N7 Co1 124.6(2) . . ?
C11 N7 Co1 120.6(2) . . ?
C11 N7 O3 114.7(3) . . ?
N9 N8 Co1 140.3(2) . . ?
N9 N8 C12 105.0(3) . . ?
C12 N8 Co1 114.3(2) . . ?
N8 N9 H9 123.9 . . ?
C14 N9 N8 112.2(3) . . ?
C14 N9 H9 123.9 . . ?
N1 C1 C2 112.0(3) . . ?
N1 C1 C5 124.2(3) . . ?
C2 C1 C5 123.8(4) . . ?
N2 C2 C1 118.4(4) . . ?
N2 C2 C3 111.0(3) . . ?
C3 C2 C1 130.6(3) . . ?
C2 C3 H3A 127.6 . . ?
C4 C3 C2 104.8(3) . . ?
C4 C3 H3A 127.6 . . ?
N3 C4 C3 107.3(4) . . ?
N3 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 C7 112.7(3) . . ?
N4 C6 C10 124.9(3) . . ?
C7 C6 C10 122.4(3) . . ?
N5 C7 C6 117.8(3) . . ?
N5 C7 C8 110.3(3) . . ?
C8 C7 C6 131.9(3) . . ?
C7 C8 H8 127.3 . . ?
C9 C8 C7 105.5(3) . . ?
C9 C8 H8 127.3 . . ?
N6 C9 C8 107.1(3) . . ?
N6 C9 H9A 126.4 . . ?
C8 C9 H9A 126.4 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 C12 112.7(3) . . ?
N7 C11 C15 123.9(3) . . ?
C12 C11 C15 123.4(3) . . ?
N8 C12 C11 117.8(3) . . ?
N8 C12 C13 110.8(3) . . ?
C13 C12 C11 131.5(4) . . ?
C12 C13 H13 127.5 . . ?
C14 C13 C12 105.1(3) . . ?
C14 C13 H13 127.5 . . ?
N9 C14 C13 106.9(3) . . ?
N9 C14 H14 126.6 . . ?
C13 C14 H14 126.6 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.3(3) . . ?
C17 C16 B1 120.5(3) . . ?
C21 C16 B1 122.2(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.5(4) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.5(4) . . ?
C20 C21 H21 119.2 . . ?
O1 B1 O3 112.7(3) . . ?
O1 B1 C16 106.8(3) . . ?
O2 B1 O1 111.5(3) . . ?
O2 B1 O3 111.2(3) . . ?
O2 B1 C16 108.8(3) . . ?
O3 B1 C16 105.5(3) . . ?
C2S C1S H1S 119.9 . . ?
C6S C1S H1S 119.9 . . ?
C6S C1S C2S 120.3(4) . . ?
C1S C2S H2S 120.2 . . ?
C1S C2S C3S 119.6(4) . . ?
C3S C2S H2S 120.2 . . ?
C2S C3S H3S 119.9 . . ?
C4S C3S C2S 120.2(4) . . ?
C4S C3S H3S 119.9 . . ?
C3S C4S H4S 120.2 . . ?
C5S C4S C3S 119.7(4) . . ?
C5S C4S H4S 120.2 . . ?
C4S C5S H5S 119.9 . . ?
C4S C5S C6S 120.2(4) . . ?
C6S C5S H5S 119.9 . . ?
C1S C6S C5S 120.0(4) . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S H6S 120.0 . . ?

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 C1 C2 -4.6(4) . . . . ?
Co1 N1 C1 C5 174.2(3) . . . . ?
Co1 N2 N3 C4 173.2(3) . . . . ?
Co1 N2 C2 C1 5.6(4) . . . . ?
Co1 N2 C2 C3 -175.2(2) . . . . ?
Co1 N4 C6 C7 -1.7(4) . . . . ?
Co1 N4 C6 C10 178.4(3) . . . . ?
Co1 N5 N6 C9 -173.8(3) . . . . ?
Co1 N5 C7 C6 -3.3(4) . . . . ?
Co1 N5 C7 C8 175.5(3) . . . . ?
Co1 N7 C11 C12 3.6(4) . . . . ?
Co1 N7 C11 C15 -175.5(3) . . . . ?
Co1 N8 N9 C14 -172.7(3) . . . . ?
Co1 N8 C12 C11 -3.0(4) . . . . ?
Co1 N8 C12 C13 175.8(3) . . . . ?
O1 N1 C1 C2 -179.7(3) . . . . ?
O1 N1 C1 C5 -0.8(5) . . . . ?
O2 N4 C6 C7 179.9(3) . . . . ?
O2 N4 C6 C10 0.0(5) . . . . ?
O3 N7 C11 C12 179.9(3) . . . . ?
O3 N7 C11 C15 0.8(5) . . . . ?
N1 O1 B1 O2 -61.7(3) . . . . ?
N1 O1 B1 O3 64.1(4) . . . . ?
N1 O1 B1 C16 179.6(3) . . . . ?
N1 C1 C2 N2 -0.9(5) . . . . ?
N1 C1 C2 C3 -179.9(4) . . . . ?
N2 N3 C4 C3 -0.2(4) . . . . ?
N2 C2 C3 C4 -0.1(4) . . . . ?
N3 N2 C2 C1 -179.2(3) . . . . ?
N3 N2 C2 C3 0.0(4) . . . . ?
N4 O2 B1 O1 61.5(3) . . . . ?
N4 O2 B1 O3 -65.2(4) . . . . ?
N4 O2 B1 C16 179.0(3) . . . . ?
N4 C6 C7 N5 3.3(5) . . . . ?
N4 C6 C7 C8 -175.2(4) . . . . ?
N5 N6 C9 C8 0.6(5) . . . . ?
N5 C7 C8 C9 0.0(5) . . . . ?
N6 N5 C7 C6 -178.4(3) . . . . ?
N6 N5 C7 C8 0.4(4) . . . . ?
N7 O3 B1 O1 -65.9(4) . . . . ?
N7 O3 B1 O2 60.1(4) . . . . ?
N7 O3 B1 C16 177.9(3) . . . . ?
N7 C11 C12 N8 -0.2(5) . . . . ?
N7 C11 C12 C13 -178.7(4) . . . . ?
N8 N9 C14 C13 -0.3(5) . . . . ?
N8 C12 C13 C14 -1.5(5) . . . . ?
N9 N8 C12 C11 -177.5(3) . . . . ?
N9 N8 C12 C13 1.3(4) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 N2 N3 C4 0.1(4) . . . . ?
C2 C3 C4 N3 0.1(4) . . . . ?
C5 C1 C2 N2 -179.8(3) . . . . ?
C5 C1 C2 C3 1.3(6) . . . . ?
C6 C7 C8 C9 178.6(4) . . . . ?
C7 N5 N6 C9 -0.6(4) . . . . ?
C7 C8 C9 N6 -0.4(5) . . . . ?
C10 C6 C7 N5 -176.8(4) . . . . ?
C10 C6 C7 C8 4.7(7) . . . . ?
C11 C12 C13 C14 177.1(4) . . . . ?
C12 N8 N9 C14 -0.6(4) . . . . ?
C12 C13 C14 N9 1.1(4) . . . . ?
C15 C11 C12 N8 178.9(4) . . . . ?
C15 C11 C12 C13 0.4(7) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C16 C21 C20 0.5(5) . . . . ?
C17 C16 B1 O1 178.3(3) . . . . ?
C17 C16 B1 O2 57.8(4) . . . . ?
C17 C16 B1 O3 -61.6(4) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C20 C21 C16 -0.5(6) . . . . ?
C21 C16 C17 C18 0.0(5) . . . . ?
C21 C16 B1 O1 -4.1(4) . . . . ?
C21 C16 B1 O2 -124.6(4) . . . . ?
C21 C16 B1 O3 116.0(4) . . . . ?
B1 O1 N1 Co1 -3.6(4) . . . . ?
B1 O1 N1 C1 171.3(3) . . . . ?
B1 O2 N4 Co1 3.1(4) . . . . ?
B1 O2 N4 C6 -178.5(3) . . . . ?
B1 O3 N7 Co1 6.6(4) . . . . ?
B1 O3 N7 C11 -169.5(3) . . . . ?
B1 C16 C17 C18 177.7(3) . . . . ?
B1 C16 C21 C20 -177.2(3) . . . . ?
C1S C2S C3S C4S 1.9(6) . . . . ?
C2S C1S C6S C5S -0.6(6) . . . . ?
C2S C3S C4S C5S -2.1(6) . . . . ?
C3S C4S C5S C6S 0.9(6) . . . . ?
C4S C5S C6S C1S 0.5(6) . . . . ?
C6S C1S C2S C3S -0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
