# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1571714'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 B2 Co F8 N12.50 O4'
_chemical_formula_weight         796.12

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.713(8)
_cell_length_b                   13.235(7)
_cell_length_c                   20.922(8)
_cell_angle_alpha                90
_cell_angle_beta                 121.21(3)
_cell_angle_gamma                90
_cell_volume                     3484(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    14329
_cell_measurement_theta_min      0.25
_cell_measurement_theta_max      30.87

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             1610
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21289
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.914
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7710
_reflns_number_gt                3634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1854P)²+1.2089P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7710
_refine_ls_number_parameters     476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1872
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.3368
_refine_ls_wR_factor_gt          0.2694
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.69461(7) 0.14872(6) 0.20288(4) 0.0536(3) Uani 1 1 d . . . . .
O2 O 0.8340(7) 0.3525(6) 0.5319(4) 0.136(3) Uani 1 1 d . . . . .
O1 O 0.7694(7) 0.4293(6) 0.4269(4) 0.124(2) Uani 1 1 d . . . . .
O3 O 0.4185(8) -0.0645(7) 0.2543(4) 0.134(3) Uani 1 1 d . . . . .
O4 O 0.2775(7) 0.0257(7) 0.2190(5) 0.150(3) Uani 1 1 d . . . . .
N11 N 0.8027(6) 0.3542(6) 0.4651(4) 0.095(2) Uani 1 1 d . . . . .
N8 N 0.6363(5) 0.2796(4) 0.1490(3) 0.0640(15) Uani 1 1 d . . . . .
N5 N 0.7604(4) 0.1706(4) 0.3201(3) 0.0547(13) Uani 1 1 d . . . . .
N1 N 0.6592(4) 0.0593(4) 0.1076(3) 0.0640(14) Uani 1 1 d . . . . .
N10 N 0.5454(4) 0.1490(4) 0.1859(3) 0.0597(14) Uani 1 1 d . . . . .
N3 N 0.7474(4) 0.0090(4) 0.2482(3) 0.0572(13) Uani 1 1 d . . . . .
N4 N 0.7949(5) -0.0019(4) 0.3243(3) 0.0647(14) Uani 1 1 d . . . . .
N9 N 0.5291(5) 0.2952(4) 0.1199(3) 0.0674(15) Uani 1 1 d . . . . .
N12 N 0.3617(9) 0.0121(9) 0.2244(5) 0.110(3) Uani 1 1 d . . . . .
N2 N 0.6234(7) -0.0811(8) -0.0012(5) 0.113(3) Uani 1 1 d . . . . .
N6 N 0.8235(5) 0.2077(6) 0.2061(3) 0.086(2) Uani 1 1 d . . . . .
C18 C 0.6817(10) 0.4529(7) 0.1205(6) 0.118(4) Uani 1 1 d . . . . .
H18A H 0.6456 0.4558 0.0670 0.177 Uiso 1 1 calc R U . . .
H18B H 0.7492 0.4861 0.1416 0.177 Uiso 1 1 calc R U . . .
H18C H 0.6396 0.4860 0.1372 0.177 Uiso 1 1 calc R U . . .
C14 C 0.9914(9) 0.2084(14) 0.2203(8) 0.158(6) Uani 1 1 d . . . . .
H14 H 1.0552 0.1746 0.2364 0.190 Uiso 1 1 calc R U . . .
C13 C 0.9175(8) 0.1620(10) 0.2313(6) 0.134(5) Uani 1 1 d . . . . .
H13 H 0.9320 0.1001 0.2557 0.161 Uiso 1 1 calc R U . . .
N7 N 0.9793(10) 0.2935(12) 0.1901(8) 0.173(5) Uani 1 1 d . . . . .
C11 C 0.8048(6) 0.2581(6) 0.4301(4) 0.0705(19) Uani 1 1 d . . . . .
C17 C 0.6986(8) 0.3438(6) 0.1454(4) 0.080(2) Uani 1 1 d . . . . .
C1 C 0.6246(6) 0.0871(7) 0.0387(4) 0.077(2) Uani 1 1 d . . . . .
H1 H 0.6125 0.1554 0.0265 0.092 Uiso 1 1 calc R U . . .
C8 C 0.7991(5) 0.0857(5) 0.3606(3) 0.0564(15) Uani 1 1 d . . . . .
C2 C 0.6056(7) 0.0180(9) -0.0166(5) 0.102(3) Uani 1 1 d . . . . .
H2 H 0.5802 0.0405 -0.0651 0.122 Uiso 1 1 calc R U . . .
C21 C 0.3761(7) 0.2352(7) 0.1252(5) 0.087(2) Uani 1 1 d . . . . .
H21 H 0.3337 0.2881 0.0955 0.104 Uiso 1 1 calc R U . . .
C4 C 0.6784(5) -0.0403(6) 0.1253(4) 0.0655(18) Uani 1 1 d . . . . .
C10 C 0.8437(6) 0.1734(7) 0.4715(4) 0.082(2) Uani 1 1 d . . . . .
H10 H 0.8718 0.1753 0.5228 0.099 Uiso 1 1 calc R U . . .
C24 C 0.5038(6) 0.0799(5) 0.2115(4) 0.0674(19) Uani 1 1 d . . . . .
H24 H 0.5460 0.0268 0.2411 0.081 Uiso 1 1 calc R U . . .
C15 C 0.8828(11) 0.3458(10) 0.1670(7) 0.131(4) Uani 1 1 d . . . . .
H15 H 0.8724 0.4105 0.1471 0.157 Uiso 1 1 calc R U . . .
C19 C 0.4605(8) 0.3613(7) 0.0559(6) 0.106(3) Uani 1 1 d . . . . .
H19A H 0.3898 0.3341 0.0289 0.159 Uiso 1 1 calc R U . . .
H19B H 0.4883 0.3652 0.0234 0.159 Uiso 1 1 calc R U . . .
H19C H 0.4588 0.4277 0.0737 0.159 Uiso 1 1 calc R U . . .
C5 C 0.7233(5) -0.0682(6) 0.2048(4) 0.0694(19) Uani 1 1 d . . . . .
C12 C 0.7629(5) 0.2550(5) 0.3539(4) 0.0650(17) Uani 1 1 d . . . . .
H12 H 0.7359 0.3138 0.3259 0.078 Uiso 1 1 calc R U . . .
C20 C 0.4843(6) 0.2261(6) 0.1442(4) 0.0675(18) Uani 1 1 d . . . . .
C9 C 0.8416(6) 0.0855(6) 0.4375(4) 0.074(2) Uani 1 1 d . . . . .
H9 H 0.8681 0.0263 0.4650 0.089 Uiso 1 1 calc R U . . .
C23 C 0.4034(7) 0.0864(7) 0.1952(4) 0.078(2) Uani 1 1 d . . . . .
C6 C 0.7292(9) -0.1768(7) 0.2259(6) 0.124(4) Uani 1 1 d . . . . .
H6A H 0.7523 -0.1818 0.2780 0.186 Uiso 1 1 calc R U . . .
H6B H 0.7788 -0.2113 0.2168 0.186 Uiso 1 1 calc R U . . .
H6C H 0.6603 -0.2072 0.1965 0.186 Uiso 1 1 calc R U . . .
C16 C 0.8058(7) 0.3000(7) 0.1742(4) 0.087(3) Uani 1 1 d . . . . .
C7 C 0.8857(7) -0.0731(8) 0.3688(5) 0.104(3) Uani 1 1 d . . . . .
H7A H 0.9461 -0.0359 0.4060 0.156 Uiso 1 1 calc R U . . .
H7B H 0.9036 -0.1066 0.3361 0.156 Uiso 1 1 calc R U . . .
H7C H 0.8654 -0.1225 0.3927 0.156 Uiso 1 1 calc R U . . .
C3 C 0.6591(7) -0.1076(8) 0.0684(6) 0.111(4) Uani 1 1 d . . . . .
H3 H 0.6723 -0.1757 0.0805 0.133 Uiso 1 1 calc R U . . .
C22 C 0.3370(7) 0.1641(8) 0.1517(5) 0.091(3) Uani 1 1 d . . . . .
H22 H 0.2673 0.1676 0.1409 0.109 Uiso 1 1 calc R U . . .
F4 F 0.5759(8) 0.1134(9) 0.3716(5) 0.217(5) Uani 1 1 d . . . . .
F2 F 0.6298(6) 0.1900(6) 0.4762(4) 0.149(2) Uani 1 1 d . . . . .
F1 F 0.5465(7) 0.2710(7) 0.3710(5) 0.203(4) Uani 1 1 d . . . . .
F3 F 0.4548(6) 0.1618(7) 0.3921(6) 0.207(5) Uani 1 1 d . . . . .
B1 B 0.5475(10) 0.1849(11) 0.4018(7) 0.100(3) Uani 1 1 d . . . . .
F5 F 0.1770(8) 0.1953(9) 0.4085(5) 0.212(4) Uani 1 1 d . . . . .
F6 F 0.1664(11) 0.1492(9) 0.4989(5) 0.290(9) Uani 1 1 d . . . . .
F7 F 0.0301(8) 0.1732(10) 0.4007(8) 0.254(6) Uani 1 1 d . . . . .
F8 F 0.1000(11) 0.0533(8) 0.4027(7) 0.251(6) Uani 1 1 d . . . . .
B2 B 0.1262(11) 0.1415(9) 0.4291(7) 0.100(3) Uani 1 1 d . . . . .
C26 C 0.049(2) 0.404(2) 0.4489(16) 0.144(9) Uiso 0.5 1 d . . P . .
C25 C 0.018(2) 0.436(2) 0.3885(18) 0.155(10) Uiso 0.5 1 d . . P . .
N13 N 0.052(2) 0.458(2) 0.3252(17) 0.195(10) Uiso 0.5 1 d . . P . .


_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 N8 2.001(6) . ?
Co1 N6 2.019(6) . ?
Co1 N10 2.034(6) . ?
Co1 N3 2.039(5) . ?
Co1 N1 2.137(5) . ?
Co1 N5 2.140(5) . ?
O2 N11 1.226(10) . ?
O1 N11 1.208(9) . ?
O3 N12 1.254(12) . ?
O4 N12 1.197(11) . ?
N11 C11 1.474(10) . ?
N8 C17 1.281(9) . ?
N8 N9 1.381(8) . ?
N5 C12 1.312(8) . ?
N5 C8 1.343(8) . ?
N1 C1 1.309(9) . ?
N1 C4 1.359(9) . ?
N10 C20 1.341(9) . ?
N10 C24 1.356(8) . ?
N3 C5 1.288(8) . ?
N3 N4 1.375(7) . ?
N4 C8 1.369(8) . ?
N4 C7 1.501(9) . ?
N9 C20 1.370(9) . ?
N9 C19 1.476(10) . ?
N12 C23 1.453(11) . ?
N2 C3 1.315(14) . ?
N2 C2 1.343(13) . ?
N6 C13 1.341(13) . ?
N6 C16 1.351(11) . ?
C18 C17 1.510(11) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 N7 1.258(17) . ?
C14 C13 1.368(15) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
N7 C15 1.420(18) . ?
C11 C10 1.350(11) . ?
C11 C12 1.381(9) . ?
C17 C16 1.484(13) . ?
C1 C2 1.385(11) . ?
C1 H1 0.9300 . ?
C8 C9 1.393(9) . ?
C2 H2 0.9300 . ?
C21 C22 1.362(12) . ?
C21 C20 1.431(11) . ?
C21 H21 0.9300 . ?
C4 C3 1.393(10) . ?
C4 C5 1.483(11) . ?
C10 C9 1.355(11) . ?
C10 H10 0.9300 . ?
C24 C23 1.334(11) . ?
C24 H24 0.9300 . ?
C15 C16 1.361(13) . ?
C15 H15 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C5 C6 1.493(12) . ?
C12 H12 0.9300 . ?
C9 H9 0.9300 . ?
C23 C22 1.384(13) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3 0.9300 . ?
C22 H22 0.9300 . ?
F4 B1 1.321(14) . ?
F2 B1 1.393(13) . ?
F1 B1 1.305(14) . ?
F3 B1 1.307(13) . ?
F5 B2 1.260(14) . ?
F6 B2 1.264(15) . ?
F7 B2 1.287(15) . ?
F8 B2 1.262(14) . ?
C26 C25 1.18(3) . ?
C25 N13 1.66(4) . ?

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
N8 Co1 N6 78.8(3) . . ?
N8 Co1 N10 77.9(2) . . ?
N6 Co1 N10 156.2(3) . . ?
N8 Co1 N3 174.6(2) . . ?
N6 Co1 N3 102.1(3) . . ?
N10 Co1 N3 101.5(2) . . ?
N8 Co1 N1 97.3(2) . . ?
N6 Co1 N1 90.9(2) . . ?
N10 Co1 N1 96.8(2) . . ?
N3 Co1 N1 77.4(2) . . ?
N8 Co1 N5 109.6(2) . . ?
N6 Co1 N5 92.9(2) . . ?
N10 Co1 N5 90.35(19) . . ?
N3 Co1 N5 75.7(2) . . ?
N1 Co1 N5 153.0(2) . . ?
O1 N11 O2 123.6(8) . . ?
O1 N11 C11 119.1(7) . . ?
O2 N11 C11 117.3(8) . . ?
C17 N8 N9 124.3(7) . . ?
C17 N8 Co1 119.8(6) . . ?
N9 N8 Co1 115.9(4) . . ?
C12 N5 C8 119.3(5) . . ?
C12 N5 Co1 127.0(4) . . ?
C8 N5 Co1 113.6(4) . . ?
C1 N1 C4 118.7(6) . . ?
C1 N1 Co1 129.7(5) . . ?
C4 N1 Co1 111.5(4) . . ?
C20 N10 C24 118.8(7) . . ?
C20 N10 Co1 114.5(5) . . ?
C24 N10 Co1 126.7(5) . . ?
C5 N3 N4 121.5(6) . . ?
C5 N3 Co1 119.5(5) . . ?
N4 N3 Co1 118.4(4) . . ?
C8 N4 N3 113.7(5) . . ?
C8 N4 C7 114.8(6) . . ?
N3 N4 C7 122.5(6) . . ?
C20 N9 N8 113.3(5) . . ?
C20 N9 C19 119.9(7) . . ?
N8 N9 C19 125.2(6) . . ?
O4 N12 O3 123.9(10) . . ?
O4 N12 C23 120.0(12) . . ?
O3 N12 C23 116.0(10) . . ?
C3 N2 C2 116.2(8) . . ?
C13 N6 C16 119.8(8) . . ?
C13 N6 Co1 126.7(7) . . ?
C16 N6 Co1 113.3(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N7 C14 C13 124.6(14) . . ?
N7 C14 H14 117.7 . . ?
C13 C14 H14 117.7 . . ?
N6 C13 C14 118.7(12) . . ?
N6 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C14 N7 C15 117.6(10) . . ?
C10 C11 C12 120.2(7) . . ?
C10 C11 N11 120.6(7) . . ?
C12 C11 N11 119.1(7) . . ?
N8 C17 C16 111.0(7) . . ?
N8 C17 C18 131.3(9) . . ?
C16 C17 C18 117.7(8) . . ?
N1 C1 C2 122.0(9) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N5 C8 N4 118.5(5) . . ?
N5 C8 C9 121.3(6) . . ?
N4 C8 C9 120.2(6) . . ?
N2 C2 C1 121.0(9) . . ?
N2 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C22 C21 C20 118.2(8) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
N1 C4 C3 117.7(8) . . ?
N1 C4 C5 117.1(6) . . ?
C3 C4 C5 125.1(8) . . ?
C11 C10 C9 119.3(7) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C23 C24 N10 121.5(7) . . ?
C23 C24 H24 119.3 . . ?
N10 C24 H24 119.3 . . ?
C16 C15 N7 119.2(12) . . ?
C16 C15 H15 120.4 . . ?
N7 C15 H15 120.4 . . ?
N9 C19 H19A 109.5 . . ?
N9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C5 C4 113.1(6) . . ?
N3 C5 C6 127.1(8) . . ?
C4 C5 C6 119.6(7) . . ?
N5 C12 C11 121.2(7) . . ?
N5 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N10 C20 N9 117.4(6) . . ?
N10 C20 C21 121.3(7) . . ?
N9 C20 C21 121.3(7) . . ?
C10 C9 C8 118.6(7) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C24 C23 C22 121.8(8) . . ?
C24 C23 N12 120.1(9) . . ?
C22 C23 N12 118.1(9) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N6 C16 C15 119.9(11) . . ?
N6 C16 C17 116.5(7) . . ?
C15 C16 C17 123.5(10) . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C3 C4 124.4(10) . . ?
N2 C3 H3 117.8 . . ?
C4 C3 H3 117.8 . . ?
C21 C22 C23 118.5(8) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
F1 B1 F3 112.5(11) . . ?
F1 B1 F4 108.3(11) . . ?
F3 B1 F4 108.7(13) . . ?
F1 B1 F2 106.9(11) . . ?
F3 B1 F2 114.7(10) . . ?
F4 B1 F2 105.2(10) . . ?
F5 B2 F8 118.3(15) . . ?
F5 B2 F6 110.0(11) . . ?
F8 B2 F6 115.7(12) . . ?
F5 B2 F7 111.2(13) . . ?
F8 B2 F7 95.0(11) . . ?
F6 B2 F7 104.6(15) . . ?
C26 C25 N13 144(3) . . ?

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
C5 N3 N4 C8 -169.8(6) . . . . ?
Co1 N3 N4 C8 0.8(7) . . . . ?
C5 N3 N4 C7 44.8(10) . . . . ?
Co1 N3 N4 C7 -144.6(6) . . . . ?
C17 N8 N9 C20 -166.8(6) . . . . ?
Co1 N8 N9 C20 10.9(6) . . . . ?
C17 N8 N9 C19 27.6(10) . . . . ?
Co1 N8 N9 C19 -154.8(6) . . . . ?
C16 N6 C13 C14 -3.4(16) . . . . ?
Co1 N6 C13 C14 171.6(10) . . . . ?
N7 C14 C13 N6 2(2) . . . . ?
C13 C14 N7 C15 1(3) . . . . ?
O1 N11 C11 C10 178.4(9) . . . . ?
O2 N11 C11 C10 -2.6(12) . . . . ?
O1 N11 C11 C12 -3.8(12) . . . . ?
O2 N11 C11 C12 175.2(8) . . . . ?
N9 N8 C17 C16 -173.7(6) . . . . ?
Co1 N8 C17 C16 8.8(8) . . . . ?
N9 N8 C17 C18 8.9(12) . . . . ?
Co1 N8 C17 C18 -168.6(7) . . . . ?
C4 N1 C1 C2 1.1(10) . . . . ?
Co1 N1 C1 C2 -179.9(6) . . . . ?
C12 N5 C8 N4 179.3(6) . . . . ?
Co1 N5 C8 N4 1.4(7) . . . . ?
C12 N5 C8 C9 0.1(9) . . . . ?
Co1 N5 C8 C9 -177.8(5) . . . . ?
N3 N4 C8 N5 -1.5(8) . . . . ?
C7 N4 C8 N5 146.7(7) . . . . ?
N3 N4 C8 C9 177.8(6) . . . . ?
C7 N4 C8 C9 -34.0(9) . . . . ?
C3 N2 C2 C1 0.1(14) . . . . ?
N1 C1 C2 N2 -0.9(13) . . . . ?
C1 N1 C4 C3 -0.7(9) . . . . ?
Co1 N1 C4 C3 -179.8(6) . . . . ?
C1 N1 C4 C5 176.6(6) . . . . ?
Co1 N1 C4 C5 -2.6(7) . . . . ?
C12 C11 C10 C9 0.2(12) . . . . ?
N11 C11 C10 C9 178.0(7) . . . . ?
C20 N10 C24 C23 1.0(9) . . . . ?
Co1 N10 C24 C23 -178.2(5) . . . . ?
C14 N7 C15 C16 -4(2) . . . . ?
N4 N3 C5 C4 -176.8(5) . . . . ?
Co1 N3 C5 C4 12.7(8) . . . . ?
N4 N3 C5 C6 7.7(11) . . . . ?
Co1 N3 C5 C6 -162.8(7) . . . . ?
N1 C4 C5 N3 -6.2(9) . . . . ?
C3 C4 C5 N3 170.8(7) . . . . ?
N1 C4 C5 C6 169.7(7) . . . . ?
C3 C4 C5 C6 -13.3(12) . . . . ?
C8 N5 C12 C11 0.2(10) . . . . ?
Co1 N5 C12 C11 177.8(5) . . . . ?
C10 C11 C12 N5 -0.3(11) . . . . ?
N11 C11 C12 N5 -178.2(7) . . . . ?
C24 N10 C20 N9 179.3(5) . . . . ?
Co1 N10 C20 N9 -1.4(7) . . . . ?
C24 N10 C20 C21 -1.4(9) . . . . ?
Co1 N10 C20 C21 177.9(5) . . . . ?
N8 N9 C20 N10 -6.1(8) . . . . ?
C19 N9 C20 N10 160.4(7) . . . . ?
N8 N9 C20 C21 174.7(6) . . . . ?
C19 N9 C20 C21 -18.9(10) . . . . ?
C22 C21 C20 N10 1.2(10) . . . . ?
C22 C21 C20 N9 -179.6(7) . . . . ?
C11 C10 C9 C8 0.0(12) . . . . ?
N5 C8 C9 C10 -0.2(10) . . . . ?
N4 C8 C9 C10 -179.4(7) . . . . ?
N10 C24 C23 C22 -0.3(11) . . . . ?
N10 C24 C23 N12 -179.0(6) . . . . ?
O4 N12 C23 C24 169.2(8) . . . . ?
O3 N12 C23 C24 -11.1(12) . . . . ?
O4 N12 C23 C22 -9.5(12) . . . . ?
O3 N12 C23 C22 170.2(8) . . . . ?
C13 N6 C16 C15 0.7(13) . . . . ?
Co1 N6 C16 C15 -174.9(8) . . . . ?
C13 N6 C16 C17 177.9(8) . . . . ?
Co1 N6 C16 C17 2.3(9) . . . . ?
N7 C15 C16 N6 2.9(16) . . . . ?
N7 C15 C16 C17 -174.1(10) . . . . ?
N8 C17 C16 N6 -7.1(10) . . . . ?
C18 C17 C16 N6 170.7(7) . . . . ?
N8 C17 C16 C15 170.0(9) . . . . ?
C18 C17 C16 C15 -12.2(13) . . . . ?
C2 N2 C3 C4 0.3(14) . . . . ?
N1 C4 C3 N2 -0.1(13) . . . . ?
C5 C4 C3 N2 -177.1(8) . . . . ?
C20 C21 C22 C23 -0.5(11) . . . . ?
C24 C23 C22 C21 0.1(12) . . . . ?
N12 C23 C22 C21 178.8(7) . . . . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.098

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1571715'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 Cl2 Co N12 O14'
_chemical_formula_weight         846.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.286(8)
_cell_length_b                   13.218(7)
_cell_length_c                   23.014(9)
_cell_angle_alpha                90
_cell_angle_beta                 128.37(2)
_cell_angle_gamma                90
_cell_volume                     3407(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8876
_cell_measurement_theta_min      0.21
_cell_measurement_theta_max      30.08

_exptl_crystal_description       block
_exptl_crystal_colour            dark-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             1724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15094
_diffrn_reflns_av_unetI/netI     0.1441
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             5878
_reflns_number_gt                2476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1420P)²+0.1296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5878
_refine_ls_number_parameters     485
_refine_ls_number_restraints     320
_refine_ls_R_factor_all          0.2278
_refine_ls_R_factor_gt           0.1234
_refine_ls_wR_factor_ref         0.3605
_refine_ls_wR_factor_gt          0.3048
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_restrained_S_all      1.353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co -0.29289(12) 0.14742(10) 0.20032(7) 0.0484(5) Uani 1 1 d . U . . .
C15 C -0.5271(15) -0.1048(11) 0.0662(8) 0.089(4) Uani 1 1 d . U . . .
H15A H -0.5181 -0.1743 0.0792 0.107 Uiso 1 1 calc R U . . .
C1 C -0.4669(13) 0.1459(12) 0.2247(8) 0.085(4) Uani 1 1 d . U . . .
H1 H -0.4348 0.0817 0.2471 0.102 Uiso 1 1 calc R U . . .
C2 C -0.5639(15) 0.1811(14) 0.2177(9) 0.107(5) Uani 1 1 d . U . . .
H2 H -0.5996 0.1383 0.2321 0.128 Uiso 1 1 calc R U . . .
C3 C -0.5565(17) 0.3279(14) 0.1727(10) 0.113(6) Uani 1 1 d . U . . .
H3 H -0.5806 0.3959 0.1569 0.136 Uiso 1 1 calc R U . . .
C4 C -0.4630(11) 0.2855(10) 0.1761(7) 0.063(3) Uani 1 1 d . U . . .
C5 C -0.4111(11) 0.3387(10) 0.1492(7) 0.073(4) Uani 1 1 d . U . . .
C6 C -0.4400(14) 0.4443(9) 0.1272(7) 0.093(5) Uani 1 1 d . U . . .
H6A H -0.4335 0.4827 0.1660 0.140 Uiso 1 1 calc R U . . .
H6B H -0.5217 0.4493 0.0807 0.140 Uiso 1 1 calc R U . . .
H6C H -0.3843 0.4720 0.1199 0.140 Uiso 1 1 calc R U . . .
C7 C -0.3445(12) 0.3649(9) 0.0614(6) 0.072(4) Uani 1 1 d . U . . .
H7A H -0.4232 0.3840 0.0462 0.109 Uiso 1 1 calc R U . . .
H7B H -0.3536 0.3344 0.0194 0.109 Uiso 1 1 calc R U . . .
H7C H -0.2940 0.4252 0.0780 0.109 Uiso 1 1 calc R U . . .
C8 C -0.1950(10) 0.2238(8) 0.1449(6) 0.055(3) Uani 1 1 d . U . . .
C9 C -0.1226(12) 0.2343(9) 0.1289(7) 0.073(4) Uani 1 1 d . U . . .
H9 H -0.1324 0.2906 0.0999 0.088 Uiso 1 1 calc R U . . .
C10 C -0.0266(11) 0.1619(10) 0.1545(7) 0.072(4) Uani 1 1 d . U . . .
H10 H 0.0244 0.1706 0.1415 0.086 Uiso 1 1 calc R U . . .
C11 C -0.0117(11) 0.0851(9) 0.1954(6) 0.061(3) Uani 1 1 d . U . . .
C12 C -0.0846(10) 0.0751(8) 0.2083(5) 0.054(3) Uani 1 1 d . U . . .
H12 H -0.0786 0.0174 0.2350 0.065 Uiso 1 1 calc R U . . .
C13 C -0.5536(10) 0.0845(9) 0.0356(6) 0.066(3) Uani 1 1 d . U . . .
H13 H -0.5700 0.1537 0.0215 0.079 Uiso 1 1 calc R U . . .
C14 C -0.6449(14) 0.0067(15) -0.0178(9) 0.096(5) Uani 1 1 d . U . . .
H14 H -0.7167 0.0269 -0.0641 0.115 Uiso 1 1 calc R U . . .
C16 C -0.4264(10) -0.0377(9) 0.1258(6) 0.060(3) Uani 1 1 d D U . . .
C17 C -0.3218(11) -0.0644(9) 0.1989(6) 0.069(3) Uani 1 1 d D U . . .
C18 C -0.2821(17) -0.1708(9) 0.2225(8) 0.111(6) Uani 1 1 d . U . . .
H18A H -0.1997 -0.1714 0.2686 0.167 Uiso 1 1 calc R U . . .
H18B H -0.2864 -0.2069 0.1838 0.167 Uiso 1 1 calc R U . . .
H18C H -0.3342 -0.2041 0.2309 0.167 Uiso 1 1 calc R U . . .
C19 C -0.1549(15) -0.0729(10) 0.3645(8) 0.091(5) Uani 1 1 d . U . . .
H19A H -0.0929 -0.1241 0.3818 0.137 Uiso 1 1 calc R U . . .
H19B H -0.2335 -0.1054 0.3339 0.137 Uiso 1 1 calc R U . . .
H19C H -0.1418 -0.0405 0.4073 0.137 Uiso 1 1 calc R U . . .
C20 C -0.0810(10) 0.0882(8) 0.3601(6) 0.054(3) Uani 1 1 d . U . . .
C21 C 0.0300(10) 0.0869(8) 0.4358(6) 0.056(3) Uani 1 1 d . U . . .
H21 H 0.0570 0.0241 0.4614 0.067 Uiso 1 1 calc R U . . .
C22 C 0.0964(11) 0.1699(9) 0.4714(7) 0.065(3) Uani 1 1 d . U . . .
H22 H 0.1679 0.1676 0.5211 0.078 Uiso 1 1 calc R U . . .
C23 C 0.0519(10) 0.2626(7) 0.4291(6) 0.050(3) Uani 1 1 d . U . . .
C24 C -0.0568(10) 0.2566(7) 0.3539(6) 0.054(3) Uani 1 1 d . U . . .
H24 H -0.0840 0.3181 0.3266 0.065 Uiso 1 1 calc R U . . .
N1 N -0.4188(10) 0.1949(9) 0.2027(5) 0.074(3) Uani 1 1 d . U . . .
N2 N -0.6100(12) 0.2729(11) 0.1914(8) 0.102(4) Uani 1 1 d . U . . .
N3 N -0.3374(8) 0.2734(7) 0.1517(5) 0.057(2) Uani 1 1 d . U . . .
N4 N -0.2887(8) 0.2917(6) 0.1223(5) 0.058(2) Uani 1 1 d . U . . .
N5 N -0.1754(8) 0.1467(6) 0.1844(4) 0.054(2) Uani 1 1 d . U . . .
N6 N 0.0889(12) 0.0095(11) 0.2239(7) 0.085(4) Uani 1 1 d . U . . .
N7 N -0.4435(8) 0.0597(7) 0.1066(5) 0.058(2) Uani 1 1 d . U . . .
N8 N -0.6247(12) -0.0834(11) -0.0003(7) 0.094(4) Uani 1 1 d . U . . .
N9 N -0.2555(8) 0.0115(6) 0.2441(5) 0.054(2) Uani 1 1 d . U . . .
N10 N -0.1494(8) 0.0016(6) 0.3217(5) 0.058(2) Uani 1 1 d . U . . .
N11 N -0.1257(7) 0.1729(6) 0.3171(4) 0.044(2) Uani 1 1 d . U . . .
N12 N 0.1237(10) 0.3492(8) 0.4663(6) 0.066(3) Uani 1 1 d . U . . .
Cl1 Cl -0.2672(3) 0.1435(2) 0.42762(17) 0.0752(10) Uani 1 1 d D U . . .
Cl2 Cl 0.2526(3) 0.1776(3) 0.40019(18) 0.0763(10) Uani 1 1 d D U . . .
O1 O 0.0933(10) -0.0654(9) 0.2521(6) 0.107(4) Uani 1 1 d . U . . .
O2 O 0.1621(11) 0.0223(9) 0.2137(7) 0.116(4) Uani 1 1 d . U . . .
O3 O 0.2298(10) 0.3518(7) 0.5323(5) 0.099(3) Uani 1 1 d . U . . .
O4 O 0.0821(9) 0.4278(7) 0.4260(5) 0.089(3) Uani 1 1 d . U . . .
O5 O -0.1507(9) 0.1514(10) 0.5030(5) 0.099(5) Uani 0.726(16) 1 d D U P A 1
O5A O -0.3995(10) 0.139(4) 0.384(2) 0.19(3) Uiso 0.274(16) 1 d D . P A 2
O6 O -0.3690(11) 0.1971(12) 0.4142(8) 0.111(6) Uani 0.726(16) 1 d D U P A 1
O6A O -0.226(5) 0.2502(17) 0.443(3) 0.48(9) Uiso 0.274(16) 1 d D . P A 2
O7 O -0.2978(13) 0.0390(6) 0.4037(7) 0.115(6) Uani 0.726(16) 1 d D U P A 1
O7A O -0.235(5) 0.092(5) 0.385(2) 0.29(5) Uiso 0.274(16) 1 d D . P A 2
O8 O -0.2442(11) 0.1985(9) 0.3820(6) 0.099(5) Uani 0.726(16) 1 d D U P A 1
O8A O -0.212(4) 0.088(3) 0.4986(15) 0.132(18) Uiso 0.274(16) 1 d D . P A 2
C25 C 0.185(2) 0.5782(16) 0.5785(12) 0.146(7) Uiso 1 1 d D . . . .
O13 O 0.310(2) 0.565(2) 0.6385(14) 0.302(12) Uiso 1 1 d D . . . .
O1W O 0.042(4) 0.333(3) 0.548(2) 0.416(19) Uiso 1 1 d . . . . .
O12 O 0.1569(8) 0.1010(7) 0.3694(5) 0.104(3) Uiso 1 1 d D . . . .
O9 O 0.3303(12) 0.1727(12) 0.4832(4) 0.105(7) Uiso 0.726(16) 1 d D . P A 1
O10 O 0.3372(9) 0.1514(8) 0.3874(6) 0.071(4) Uiso 0.726(16) 1 d D . P A 1
O11 O 0.2034(13) 0.2801(7) 0.3729(8) 0.097(5) Uiso 0.726(16) 1 d D . P A 1
O12A O 0.1517(17) 0.2442(17) 0.3477(10) 0.051(8) Uiso 0.274(16) 1 d D . P A 2
O11A O 0.332(2) 0.207(2) 0.4766(7) 0.051(9) Uiso 0.274(16) 1 d D . P A 2
O9A O 0.292(4) 0.109(4) 0.3701(17) 0.17(2) Uiso 0.274(16) 1 d D . 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 N3 1.883(9) . ?
Co1 N5 1.928(10) . ?
Co1 N1 1.937(11) . ?
Co1 N9 1.965(9) . ?
Co1 N7 2.206(9) . ?
Co1 N11 2.251(8) . ?
C15 N8 1.311(18) . ?
C15 C16 1.512(16) . ?
C15 H15A 0.9500 . ?
C1 N1 1.257(16) . ?
C1 C2 1.373(19) . ?
C1 H1 0.9500 . ?
C2 N2 1.333(18) . ?
C2 H2 0.9500 . ?
C3 N2 1.31(2) . ?
C3 C4 1.405(19) . ?
C3 H3 0.9500 . ?
C4 N1 1.315(15) . ?
C4 C5 1.411(18) . ?
C5 N3 1.335(14) . ?
C5 C6 1.455(16) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N4 1.466(13) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N5 1.276(13) . ?
C8 C9 1.303(16) . ?
C8 N4 1.416(14) . ?
C9 C10 1.463(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.310(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.254(15) . ?
C11 N6 1.524(17) . ?
C12 N5 1.412(13) . ?
C12 H12 0.9500 . ?
C13 N7 1.435(14) . ?
C13 C14 1.510(18) . ?
C13 H13 0.9500 . ?
C14 N8 1.233(19) . ?
C14 H14 0.9500 . ?
C16 N7 1.333(13) . ?
C16 C17 1.437(9) . ?
C17 N9 1.328(14) . ?
C17 C18 1.487(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N10 1.429(14) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N11 1.363(12) . ?
C20 N10 1.405(13) . ?
C20 C21 1.456(15) . ?
C21 C22 1.345(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.445(15) . ?
C22 H22 0.9500 . ?
C23 N12 1.417(14) . ?
C23 C24 1.441(14) . ?
C24 N11 1.370(12) . ?
C24 H24 0.9500 . ?
N3 N4 1.258(12) . ?
N6 O1 1.164(15) . ?
N6 O2 1.218(15) . ?
N9 N10 1.464(13) . ?
N12 O4 1.268(12) . ?
N12 O3 1.322(13) . ?
Cl1 O7 1.450(7) . ?
Cl1 O6 1.468(7) . ?
Cl1 O8 1.472(7) . ?
Cl1 O5 1.485(7) . ?
Cl1 O6A 1.486(10) . ?
Cl1 O7A 1.491(10) . ?
Cl1 O5A 1.494(10) . ?
Cl1 O8A 1.496(10) . ?
Cl2 O11A 1.434(9) . ?
Cl2 O9A 1.442(9) . ?
Cl2 O10 1.451(7) . ?
Cl2 O12A 1.467(9) . ?
Cl2 O11 1.475(8) . ?
Cl2 O12 1.481(7) . ?
Cl2 O9 1.501(8) . ?
C25 O13 1.435(10) . ?

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
N3 Co1 N5 84.5(4) . . ?
N3 Co1 N1 75.7(5) . . ?
N5 Co1 N1 160.1(5) . . ?
N3 Co1 N9 175.9(4) . . ?
N5 Co1 N9 95.9(4) . . ?
N1 Co1 N9 104.1(4) . . ?
N3 Co1 N7 96.9(4) . . ?
N5 Co1 N7 104.3(3) . . ?
N1 Co1 N7 80.7(4) . . ?
N9 Co1 N7 79.1(4) . . ?
N3 Co1 N11 107.1(3) . . ?
N5 Co1 N11 79.8(3) . . ?
N1 Co1 N11 103.5(3) . . ?
N9 Co1 N11 77.0(3) . . ?
N7 Co1 N11 156.0(3) . . ?
N8 C15 C16 131.0(14) . . ?
N8 C15 H15A 114.5 . . ?
C16 C15 H15A 114.5 . . ?
N1 C1 C2 122.8(16) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
N2 C2 C1 122.7(17) . . ?
N2 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
N2 C3 C4 119.4(15) . . ?
N2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
N1 C4 C3 123.7(14) . . ?
N1 C4 C5 115.2(11) . . ?
C3 C4 C5 121.1(14) . . ?
N3 C5 C4 105.9(11) . . ?
N3 C5 C6 132.9(14) . . ?
C4 C5 C6 121.2(12) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C8 C9 115.2(12) . . ?
N5 C8 N4 120.5(11) . . ?
C9 C8 N4 124.4(11) . . ?
C8 C9 C10 121.8(12) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 119.4(12) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 117.6(12) . . ?
C12 C11 N6 121.9(13) . . ?
C10 C11 N6 120.5(13) . . ?
C11 C12 N5 122.3(11) . . ?
C11 C12 H12 118.8 . . ?
N5 C12 H12 118.8 . . ?
N7 C13 C14 123.6(12) . . ?
N7 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
N8 C14 C13 118.9(15) . . ?
N8 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N7 C16 C17 117.9(9) . . ?
N7 C16 C15 112.9(11) . . ?
C17 C16 C15 129.0(11) . . ?
N9 C17 C16 116.7(10) . . ?
N9 C17 C18 120.2(11) . . ?
C16 C17 C18 122.9(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N10 C19 H19A 109.5 . . ?
N10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N11 C20 N10 112.5(10) . . ?
N11 C20 C21 123.4(9) . . ?
N10 C20 C21 124.0(9) . . ?
C22 C21 C20 123.5(10) . . ?
C22 C21 H21 118.3 . . ?
C20 C21 H21 118.3 . . ?
C21 C22 C23 115.6(11) . . ?
C21 C22 H22 122.2 . . ?
C23 C22 H22 122.2 . . ?
N12 C23 C24 127.4(9) . . ?
N12 C23 C22 115.3(10) . . ?
C24 C23 C22 117.3(9) . . ?
N11 C24 C23 127.8(9) . . ?
N11 C24 H24 116.1 . . ?
C23 C24 H24 116.1 . . ?
C1 N1 C4 115.6(12) . . ?
C1 N1 Co1 126.4(10) . . ?
C4 N1 Co1 117.9(10) . . ?
C3 N2 C2 115.5(14) . . ?
N4 N3 C5 122.5(11) . . ?
N4 N3 Co1 113.2(7) . . ?
C5 N3 Co1 124.3(10) . . ?
N3 N4 C8 113.2(9) . . ?
N3 N4 C7 119.1(10) . . ?
C8 N4 C7 126.7(10) . . ?
C8 N5 C12 123.7(11) . . ?
C8 N5 Co1 107.4(8) . . ?
C12 N5 Co1 128.8(8) . . ?
O1 N6 O2 118.0(14) . . ?
O1 N6 C11 120.5(15) . . ?
O2 N6 C11 121.3(15) . . ?
C16 N7 C13 116.4(9) . . ?
C16 N7 Co1 108.4(7) . . ?
C13 N7 Co1 135.0(7) . . ?
C14 N8 C15 116.9(13) . . ?
C17 N9 N10 125.7(9) . . ?
C17 N9 Co1 117.0(8) . . ?
N10 N9 Co1 117.0(6) . . ?
C20 N10 C19 116.2(10) . . ?
C20 N10 N9 118.9(8) . . ?
C19 N10 N9 116.4(9) . . ?
C20 N11 C24 112.4(9) . . ?
C20 N11 Co1 114.6(7) . . ?
C24 N11 Co1 133.0(6) . . ?
O4 N12 O3 120.1(10) . . ?
O4 N12 C23 112.6(10) . . ?
O3 N12 C23 126.8(10) . . ?
O7 Cl1 O6 110.7(8) . . ?
O7 Cl1 O8 110.3(7) . . ?
O6 Cl1 O8 104.0(7) . . ?
O7 Cl1 O5 111.5(7) . . ?
O6 Cl1 O5 117.2(7) . . ?
O8 Cl1 O5 102.4(7) . . ?
O6A Cl1 O7A 110.1(14) . . ?
O6A Cl1 O5A 110.5(14) . . ?
O7A Cl1 O5A 109.0(13) . . ?
O6A Cl1 O8A 110.7(14) . . ?
O7A Cl1 O8A 109.0(13) . . ?
O5A Cl1 O8A 107.4(13) . . ?
O11A Cl2 O9A 120.7(14) . . ?
O11A Cl2 O12A 118.3(11) . . ?
O9A Cl2 O12A 117.0(13) . . ?
O10 Cl2 O11 111.7(7) . . ?
O11A Cl2 O12 124.5(14) . . ?
O9A Cl2 O12 82(2) . . ?
O10 Cl2 O12 112.2(6) . . ?
O12A Cl2 O12 82.7(12) . . ?
O11 Cl2 O12 111.7(7) . . ?
O10 Cl2 O9 101.4(7) . . ?
O11 Cl2 O9 111.2(8) . . ?
O12 Cl2 O9 108.3(7) . . ?

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
N1 C1 C2 N2 -5(3) . . . . ?
N2 C3 C4 N1 -5(2) . . . . ?
N2 C3 C4 C5 173.4(15) . . . . ?
N1 C4 C5 N3 6.8(15) . . . . ?
C3 C4 C5 N3 -172.2(12) . . . . ?
N1 C4 C5 C6 -171.9(11) . . . . ?
C3 C4 C5 C6 9(2) . . . . ?
N5 C8 C9 C10 0.4(17) . . . . ?
N4 C8 C9 C10 179.4(10) . . . . ?
C8 C9 C10 C11 -1.0(18) . . . . ?
C9 C10 C11 C12 2.8(18) . . . . ?
C9 C10 C11 N6 -178.9(10) . . . . ?
C10 C11 C12 N5 -4.2(17) . . . . ?
N6 C11 C12 N5 177.6(9) . . . . ?
N7 C13 C14 N8 0(2) . . . . ?
N8 C15 C16 N7 2(2) . . . . ?
N8 C15 C16 C17 178.6(14) . . . . ?
N7 C16 C17 N9 5.9(16) . . . . ?
C15 C16 C17 N9 -170.7(11) . . . . ?
N7 C16 C17 C18 -169.6(11) . . . . ?
C15 C16 C17 C18 14(2) . . . . ?
N11 C20 C21 C22 2.8(17) . . . . ?
N10 C20 C21 C22 178.2(11) . . . . ?
C20 C21 C22 C23 -1.1(17) . . . . ?
C21 C22 C23 N12 -178.6(10) . . . . ?
C21 C22 C23 C24 -0.6(16) . . . . ?
N12 C23 C24 N11 178.8(10) . . . . ?
C22 C23 C24 N11 1.1(17) . . . . ?
C2 C1 N1 C4 4(2) . . . . ?
C2 C1 N1 Co1 -173.2(11) . . . . ?
C3 C4 N1 C1 1.0(19) . . . . ?
C5 C4 N1 C1 -178.0(12) . . . . ?
C3 C4 N1 Co1 178.3(11) . . . . ?
C5 C4 N1 Co1 -0.7(14) . . . . ?
C4 C3 N2 C2 5(2) . . . . ?
C1 C2 N2 C3 0(3) . . . . ?
C4 C5 N3 N4 170.1(10) . . . . ?
C6 C5 N3 N4 -11(2) . . . . ?
C4 C5 N3 Co1 -11.2(13) . . . . ?
C6 C5 N3 Co1 167.3(11) . . . . ?
N5 Co1 N3 N4 10.2(7) . . . . ?
N1 Co1 N3 N4 -172.2(8) . . . . ?
N7 Co1 N3 N4 -93.6(8) . . . . ?
N11 Co1 N3 N4 87.8(8) . . . . ?
N5 Co1 N3 C5 -168.6(9) . . . . ?
N1 Co1 N3 C5 9.0(9) . . . . ?
N7 Co1 N3 C5 87.6(9) . . . . ?
N11 Co1 N3 C5 -91.0(9) . . . . ?
C5 N3 N4 C8 167.0(9) . . . . ?
Co1 N3 N4 C8 -11.9(11) . . . . ?
C5 N3 N4 C7 -23.5(15) . . . . ?
Co1 N3 N4 C7 157.7(8) . . . . ?
N5 C8 N4 N3 7.3(14) . . . . ?
C9 C8 N4 N3 -171.6(11) . . . . ?
N5 C8 N4 C7 -161.3(10) . . . . ?
C9 C8 N4 C7 19.8(17) . . . . ?
C9 C8 N5 C12 -1.7(15) . . . . ?
N4 C8 N5 C12 179.3(8) . . . . ?
C9 C8 N5 Co1 -179.9(8) . . . . ?
N4 C8 N5 Co1 1.1(11) . . . . ?
C11 C12 N5 C8 3.9(16) . . . . ?
C11 C12 N5 Co1 -178.3(8) . . . . ?
C12 C11 N6 O1 8.0(19) . . . . ?
C10 C11 N6 O1 -170.2(13) . . . . ?
C12 C11 N6 O2 -176.8(12) . . . . ?
C10 C11 N6 O2 5.0(18) . . . . ?
C17 C16 N7 C13 -175.0(10) . . . . ?
C15 C16 N7 C13 2.1(14) . . . . ?
C17 C16 N7 Co1 0.9(12) . . . . ?
C15 C16 N7 Co1 178.0(8) . . . . ?
C14 C13 N7 C16 -3.0(16) . . . . ?
C14 C13 N7 Co1 -177.5(8) . . . . ?
C13 C14 N8 C15 4(2) . . . . ?
C16 C15 N8 C14 -5(2) . . . . ?
C16 C17 N9 N10 176.6(9) . . . . ?
C18 C17 N9 N10 -7.8(17) . . . . ?
C16 C17 N9 Co1 -10.4(14) . . . . ?
C18 C17 N9 Co1 165.2(9) . . . . ?
N11 C20 N10 C19 -147.2(10) . . . . ?
C21 C20 N10 C19 36.9(16) . . . . ?
N11 C20 N10 N9 -0.3(13) . . . . ?
C21 C20 N10 N9 -176.2(9) . . . . ?
C17 N9 N10 C20 172.9(10) . . . . ?
Co1 N9 N10 C20 0.0(12) . . . . ?
C17 N9 N10 C19 -40.2(15) . . . . ?
Co1 N9 N10 C19 146.9(8) . . . . ?
N10 C20 N11 C24 -178.1(9) . . . . ?
C21 C20 N11 C24 -2.2(14) . . . . ?
N10 C20 N11 Co1 0.4(11) . . . . ?
C21 C20 N11 Co1 176.3(8) . . . . ?
C23 C24 N11 C20 0.3(15) . . . . ?
C23 C24 N11 Co1 -177.8(8) . . . . ?
C24 C23 N12 O4 0.6(16) . . . . ?
C22 C23 N12 O4 178.3(10) . . . . ?
C24 C23 N12 O3 -171.9(11) . . . . ?
C22 C23 N12 O3 5.8(16) . . . . ?

_refine_diff_density_max         1.596
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.153

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1_296K
_database_code_depnum_ccdc_archive 'CCDC 1571718'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Cl Co N10 O4'
_chemical_formula_weight         582.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.472(10)
_cell_length_b                   9.580(11)
_cell_length_c                   27.64(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.09(3)
_cell_angle_gamma                90
_cell_volume                     2215(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3012
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      25.06

_exptl_crystal_description       block
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.953
_shelx_estimated_absorpt_T_min   0.763
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8060
_diffrn_reflns_av_unetI/netI     0.1206
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_Laue_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.864
_reflns_number_total             3756
_reflns_number_gt                2490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0977P)²+92.0130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3756
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2230
_refine_ls_R_factor_gt           0.1643
_refine_ls_wR_factor_ref         0.4227
_refine_ls_wR_factor_gt          0.3939
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.1901(2) 0.3431(3) 0.11938(7) 0.0283(6) Uani 1 1 d . . . . .
N6 N 0.1260(14) 0.4695(18) 0.1630(5) 0.038(4) Uani 1 1 d . . . . .
N3 N 0.1979(16) 0.1913(13) 0.1591(4) 0.028(3) Uani 1 1 d . . . . .
N1 N 0.4056(14) 0.3542(15) 0.1477(4) 0.030(3) Uani 1 1 d . . . . .
N7 N 0.0305(19) 0.686(2) 0.2169(6) 0.056(5) Uani 1 1 d . . . . .
N5 N -0.0194(16) 0.2859(15) 0.1001(4) 0.031(3) Uani 1 1 d . . . . .
N10 N 0.2433(15) 0.2593(16) 0.0634(4) 0.030(3) Uani 1 1 d . . . . .
N8 N 0.1834(15) 0.5030(16) 0.0799(4) 0.032(3) Uani 1 1 d . . . . .
N2 N 0.7146(17) 0.337(2) 0.1946(6) 0.050(4) Uani 1 1 d . . . . .
N4 N 0.0637(17) 0.1179(16) 0.1576(5) 0.036(3) Uani 1 1 d . . . . .
N9 N 0.2265(18) 0.4863(17) 0.0368(5) 0.041(4) Uani 1 1 d . . . . .
C21 C 0.299(2) 0.077(2) 0.0133(7) 0.049(5) Uani 1 1 d . . . . .
H21 H 0.3136 -0.0178 0.0076 0.059 Uiso 1 1 calc R U . . .
C20 C 0.314(3) 0.180(3) -0.0227(7) 0.064(7) Uani 1 1 d . . . . .
H20 H 0.3380 0.1527 -0.0530 0.077 Uiso 1 1 calc R U . . .
C19 C 0.295(3) 0.309(2) -0.0141(6) 0.047(5) Uani 1 1 d . . . . .
H19 H 0.3077 0.3748 -0.0379 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1069(19) 0.605(2) 0.1458(6) 0.037(4) Uani 1 1 d . . . . .
C16 C 0.1455(19) 0.613(2) 0.0973(6) 0.036(4) Uani 1 1 d . . . . .
C12 C 0.097(2) 0.448(3) 0.2086(6) 0.054(6) Uani 1 1 d . . . . .
H12 H 0.1081 0.3597 0.2224 0.065 Uiso 1 1 calc R U . . .
C9 C -0.311(2) 0.170(3) 0.0806(8) 0.058(6) Uani 1 1 d . . . . .
H9 H -0.4150 0.1353 0.0756 0.070 Uiso 1 1 calc R U . . .
C10 C -0.278(2) 0.277(2) 0.0546(6) 0.039(4) Uani 1 1 d . . . . .
H10 H -0.3536 0.3108 0.0292 0.047 Uiso 1 1 calc R U . . .
C14 C 0.055(2) 0.701(2) 0.1715(8) 0.053(5) Uani 1 1 d . . . . .
H14 H 0.0337 0.7883 0.1569 0.063 Uiso 1 1 calc R U . . .
C17 C 0.134(3) 0.741(2) 0.0696(8) 0.050(5) Uani 1 1 d . . . . .
H17A H 0.1994 0.7352 0.0443 0.075 Uiso 1 1 calc R U . . .
H17B H 0.1702 0.8176 0.0911 0.075 Uiso 1 1 calc R U . . .
H17C H 0.0249 0.7570 0.0551 0.075 Uiso 1 1 calc R U . . .
C1 C 0.5183(19) 0.4434(16) 0.1388(6) 0.029(3) Uani 1 1 d . . . . .
H1 H 0.4928 0.5150 0.1162 0.035 Uiso 1 1 calc R U . . .
C2 C 0.669(2) 0.430(2) 0.1624(7) 0.040(4) Uani 1 1 d . . . . .
H2 H 0.7455 0.4924 0.1547 0.048 Uiso 1 1 calc R U . . .
C6 C 0.338(3) 0.057(2) 0.2248(8) 0.054(5) Uani 1 1 d . . . . .
H6A H 0.3272 0.0961 0.2562 0.081 Uiso 1 1 calc R U . . .
H6B H 0.4404 0.0121 0.2271 0.081 Uiso 1 1 calc R U . . .
H6C H 0.2549 -0.0093 0.2152 0.081 Uiso 1 1 calc R U . . .
C5 C 0.328(2) 0.167(2) 0.1894(6) 0.040(4) Uani 1 1 d . . . . .
C13 C 0.051(2) 0.558(3) 0.2348(7) 0.050(5) Uani 1 1 d . . . . .
H13 H 0.0342 0.5418 0.2668 0.060 Uiso 1 1 calc R U . . .
C3 C 0.607(2) 0.249(2) 0.2043(7) 0.042(4) Uani 1 1 d . . . . .
H3 H 0.6369 0.1801 0.2276 0.050 Uiso 1 1 calc R U . . .
C11 C -0.132(2) 0.339(2) 0.0649(6) 0.046(5) Uani 1 1 d . . . . .
H11 H -0.1102 0.4176 0.0475 0.055 Uiso 1 1 calc R U . . .
C18 C 0.2549(19) 0.352(2) 0.0295(6) 0.042(5) Uani 1 1 d . . . . .
C8 C -0.202(2) 0.110(2) 0.1143(7) 0.042(4) Uani 1 1 d . . . . .
H8 H -0.2251 0.0282 0.1300 0.051 Uiso 1 1 calc R U . . .
C4 C 0.450(2) 0.255(2) 0.1815(6) 0.043(5) Uani 1 1 d . . . . .
C22 C 0.264(2) 0.1223(18) 0.0552(6) 0.034(4) Uani 1 1 d . . . . .
H22 H 0.2529 0.0585 0.0798 0.041 Uiso 1 1 calc R U . . .
C7 C -0.049(2) 0.173(2) 0.1252(6) 0.038(4) Uani 1 1 d . . . . .
Cl1 Cl 0.5578(6) 0.8176(6) 0.15842(18) 0.0508(13) Uani 1 1 d . . . . .
O3 O 0.487(2) 0.928(2) 0.1301(7) 0.079(5) Uani 1 1 d . . . . .
O4 O 0.654(2) 0.871(2) 0.1985(7) 0.102(7) Uani 1 1 d . . . . .
O2 O 0.643(3) 0.739(2) 0.1291(8) 0.116(9) Uani 1 1 d . . . . .
O1 O 0.443(2) 0.730(2) 0.1740(7) 0.086(6) 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 N3 1.817(12) . ?
Co1 N6 1.851(15) . ?
Co1 N5 1.853(13) . ?
Co1 N10 1.861(13) . ?
Co1 N1 1.872(13) . ?
Co1 N8 1.877(14) . ?
N6 C12 1.34(2) . ?
N6 C15 1.38(2) . ?
N3 C5 1.30(2) . ?
N3 N4 1.332(19) . ?
N1 C1 1.333(19) . ?
N1 C4 1.35(2) . ?
N7 C14 1.31(3) . ?
N7 C13 1.32(3) . ?
N5 C7 1.33(2) . ?
N5 C11 1.35(2) . ?
N10 C18 1.30(2) . ?
N10 C22 1.35(2) . ?
N8 C16 1.22(2) . ?
N8 N9 1.309(18) . ?
N2 C2 1.27(3) . ?
N2 C3 1.30(3) . ?
N4 C7 1.31(2) . ?
N9 C18 1.33(3) . ?
C21 C22 1.32(2) . ?
C21 C20 1.42(3) . ?
C21 H21 0.9300 . ?
C20 C19 1.27(3) . ?
C20 H20 0.9300 . ?
C19 C18 1.37(2) . ?
C19 H19 0.9300 . ?
C15 C14 1.29(3) . ?
C15 C16 1.43(2) . ?
C16 C17 1.45(3) . ?
C12 C13 1.36(3) . ?
C12 H12 0.9300 . ?
C9 C10 1.31(3) . ?
C9 C8 1.34(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.36(2) . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C1 C2 1.35(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C6 C5 1.43(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 C4 1.38(3) . ?
C13 H13 0.9300 . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C8 C7 1.41(2) . ?
C8 H8 0.9300 . ?
C22 H22 0.9300 . ?
Cl1 O4 1.366(18) . ?
Cl1 O2 1.385(19) . ?
Cl1 O3 1.394(17) . ?
Cl1 O1 1.399(16) . ?

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
N3 Co1 N6 96.7(6) . . ?
N3 Co1 N5 83.1(6) . . ?
N6 Co1 N5 90.8(6) . . ?
N3 Co1 N10 99.6(6) . . ?
N6 Co1 N10 163.5(7) . . ?
N5 Co1 N10 88.9(6) . . ?
N3 Co1 N1 81.6(6) . . ?
N6 Co1 N1 93.3(6) . . ?
N5 Co1 N1 164.4(6) . . ?
N10 Co1 N1 91.3(6) . . ?
N3 Co1 N8 178.4(6) . . ?
N6 Co1 N8 81.9(7) . . ?
N5 Co1 N8 97.7(6) . . ?
N10 Co1 N8 81.8(6) . . ?
N1 Co1 N8 97.7(6) . . ?
C12 N6 C15 116.0(18) . . ?
C12 N6 Co1 129.2(17) . . ?
C15 N6 Co1 114.8(11) . . ?
C5 N3 N4 123.9(14) . . ?
C5 N3 Co1 118.9(13) . . ?
N4 N3 Co1 117.0(11) . . ?
C1 N1 C4 116.7(14) . . ?
C1 N1 Co1 129.7(11) . . ?
C4 N1 Co1 113.5(12) . . ?
C14 N7 C13 115.4(19) . . ?
C7 N5 C11 120.5(15) . . ?
C7 N5 Co1 110.1(11) . . ?
C11 N5 Co1 129.3(12) . . ?
C18 N10 C22 121.1(15) . . ?
C18 N10 Co1 111.0(13) . . ?
C22 N10 Co1 127.8(11) . . ?
C16 N8 N9 126.3(16) . . ?
C16 N8 Co1 117.4(11) . . ?
N9 N8 Co1 116.2(13) . . ?
C2 N2 C3 116.9(17) . . ?
C7 N4 N3 109.6(14) . . ?
N8 N9 C18 109.8(15) . . ?
C22 C21 C20 116(2) . . ?
C22 C21 H21 121.9 . . ?
C20 C21 H21 121.9 . . ?
C19 C20 C21 121.1(18) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C19 C18 121(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C14 C15 N6 121.2(16) . . ?
C14 C15 C16 128.8(19) . . ?
N6 C15 C16 110.0(16) . . ?
N8 C16 C15 115.9(17) . . ?
N8 C16 C17 121.8(16) . . ?
C15 C16 C17 122.3(18) . . ?
N6 C12 C13 120(2) . . ?
N6 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C10 C9 C8 122.4(18) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 119.6(18) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C15 C14 N7 124(2) . . ?
C15 C14 H14 117.8 . . ?
N7 C14 H14 117.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C1 C2 120.1(16) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
N2 C2 C1 124.4(18) . . ?
N2 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C5 C4 111.7(15) . . ?
N3 C5 C6 122.2(18) . . ?
C4 C5 C6 126.1(18) . . ?
N7 C13 C12 123.1(18) . . ?
N7 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
N2 C3 C4 122.4(19) . . ?
N2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
N5 C11 C10 120.4(19) . . ?
N5 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N10 C18 N9 120.9(16) . . ?
N10 C18 C19 119(2) . . ?
N9 C18 C19 120.0(18) . . ?
C9 C8 C7 118.1(19) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
N1 C4 C3 119.4(18) . . ?
N1 C4 C5 113.9(15) . . ?
C3 C4 C5 126.7(18) . . ?
C21 C22 N10 121.6(17) . . ?
C21 C22 H22 119.2 . . ?
N10 C22 H22 119.2 . . ?
N4 C7 N5 120.2(15) . . ?
N4 C7 C8 121.1(18) . . ?
N5 C7 C8 118.7(18) . . ?
O4 Cl1 O2 112.0(16) . . ?
O4 Cl1 O3 108.8(14) . . ?
O2 Cl1 O3 107.3(13) . . ?
O4 Cl1 O1 109.2(13) . . ?
O2 Cl1 O1 107.8(12) . . ?
O3 Cl1 O1 111.7(12) . . ?

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
N3 Co1 N6 C12 0.1(15) . . . . ?
N5 Co1 N6 C12 83.2(14) . . . . ?
N10 Co1 N6 C12 172.0(18) . . . . ?
N1 Co1 N6 C12 -81.8(14) . . . . ?
N8 Co1 N6 C12 -179.1(14) . . . . ?
N3 Co1 N6 C15 179.4(11) . . . . ?
N5 Co1 N6 C15 -97.5(11) . . . . ?
N10 Co1 N6 C15 -9(3) . . . . ?
N1 Co1 N6 C15 97.6(11) . . . . ?
N8 Co1 N6 C15 0.2(11) . . . . ?
N6 Co1 N3 C5 -86.8(13) . . . . ?
N5 Co1 N3 C5 -176.8(13) . . . . ?
N10 Co1 N3 C5 95.6(13) . . . . ?
N1 Co1 N3 C5 5.6(12) . . . . ?
N6 Co1 N3 N4 88.5(11) . . . . ?
N5 Co1 N3 N4 -1.6(10) . . . . ?
N10 Co1 N3 N4 -89.2(11) . . . . ?
N1 Co1 N3 N4 -179.2(11) . . . . ?
N3 Co1 N1 C1 177.0(14) . . . . ?
N6 Co1 N1 C1 -86.8(14) . . . . ?
N5 Co1 N1 C1 168.1(17) . . . . ?
N10 Co1 N1 C1 77.4(14) . . . . ?
N8 Co1 N1 C1 -4.5(14) . . . . ?
N3 Co1 N1 C4 -2.0(12) . . . . ?
N6 Co1 N1 C4 94.2(12) . . . . ?
N5 Co1 N1 C4 -11(3) . . . . ?
N10 Co1 N1 C4 -101.6(12) . . . . ?
N8 Co1 N1 C4 176.5(12) . . . . ?
N3 Co1 N5 C7 1.2(10) . . . . ?
N6 Co1 N5 C7 -95.4(11) . . . . ?
N10 Co1 N5 C7 101.0(11) . . . . ?
N1 Co1 N5 C7 10(3) . . . . ?
N8 Co1 N5 C7 -177.4(10) . . . . ?
N3 Co1 N5 C11 -175.7(15) . . . . ?
N6 Co1 N5 C11 87.7(15) . . . . ?
N10 Co1 N5 C11 -75.9(15) . . . . ?
N1 Co1 N5 C11 -166.9(18) . . . . ?
N8 Co1 N5 C11 5.7(15) . . . . ?
N3 Co1 N10 C18 -176.2(11) . . . . ?
N6 Co1 N10 C18 12(3) . . . . ?
N5 Co1 N10 C18 101.0(12) . . . . ?
N1 Co1 N10 C18 -94.5(12) . . . . ?
N8 Co1 N10 C18 3.1(11) . . . . ?
N3 Co1 N10 C22 6.0(15) . . . . ?
N6 Co1 N10 C22 -165.9(17) . . . . ?
N5 Co1 N10 C22 -76.8(15) . . . . ?
N1 Co1 N10 C22 87.6(15) . . . . ?
N8 Co1 N10 C22 -174.8(15) . . . . ?
N6 Co1 N8 C16 0.7(12) . . . . ?
N5 Co1 N8 C16 90.4(13) . . . . ?
N10 Co1 N8 C16 178.1(13) . . . . ?
N1 Co1 N8 C16 -91.6(13) . . . . ?
N6 Co1 N8 N9 178.0(12) . . . . ?
N5 Co1 N8 N9 -92.3(12) . . . . ?
N10 Co1 N8 N9 -4.5(12) . . . . ?
N1 Co1 N8 N9 85.7(12) . . . . ?
C5 N3 N4 C7 176.4(15) . . . . ?
Co1 N3 N4 C7 1.5(16) . . . . ?
C16 N8 N9 C18 -178.2(16) . . . . ?
Co1 N8 N9 C18 4.7(18) . . . . ?
C22 C21 C20 C19 0(3) . . . . ?
C21 C20 C19 C18 -2(3) . . . . ?
C12 N6 C15 C14 -4(2) . . . . ?
Co1 N6 C15 C14 176.5(15) . . . . ?
C12 N6 C15 C16 178.5(14) . . . . ?
Co1 N6 C15 C16 -0.9(17) . . . . ?
N9 N8 C16 C15 -178.4(15) . . . . ?
Co1 N8 C16 C15 -1.4(19) . . . . ?
N9 N8 C16 C17 4(3) . . . . ?
Co1 N8 C16 C17 -178.9(13) . . . . ?
C14 C15 C16 N8 -175.7(19) . . . . ?
N6 C15 C16 N8 1(2) . . . . ?
C14 C15 C16 C17 2(3) . . . . ?
N6 C15 C16 C17 179.0(15) . . . . ?
C15 N6 C12 C13 0(2) . . . . ?
Co1 N6 C12 C13 179.6(13) . . . . ?
C8 C9 C10 C11 -7(3) . . . . ?
N6 C15 C14 N7 7(3) . . . . ?
C16 C15 C14 N7 -176.4(18) . . . . ?
C13 N7 C14 C15 -5(3) . . . . ?
C4 N1 C1 C2 1(2) . . . . ?
Co1 N1 C1 C2 -177.7(13) . . . . ?
C3 N2 C2 C1 1(3) . . . . ?
N1 C1 C2 N2 -2(3) . . . . ?
N4 N3 C5 C4 177.4(14) . . . . ?
Co1 N3 C5 C4 -8(2) . . . . ?
N4 N3 C5 C6 -1(3) . . . . ?
Co1 N3 C5 C6 174.0(14) . . . . ?
C14 N7 C13 C12 1(3) . . . . ?
N6 C12 C13 N7 1(3) . . . . ?
C2 N2 C3 C4 0(3) . . . . ?
C7 N5 C11 C10 0(2) . . . . ?
Co1 N5 C11 C10 176.7(13) . . . . ?
C9 C10 C11 N5 3(3) . . . . ?
C22 N10 C18 N9 176.6(16) . . . . ?
Co1 N10 C18 N9 -1(2) . . . . ?
C22 N10 C18 C19 -3(3) . . . . ?
Co1 N10 C18 C19 179.5(14) . . . . ?
N8 N9 C18 N10 -2(2) . . . . ?
N8 N9 C18 C19 177.0(16) . . . . ?
C20 C19 C18 N10 3(3) . . . . ?
C20 C19 C18 N9 -176(2) . . . . ?
C10 C9 C8 C7 7(3) . . . . ?
C1 N1 C4 C3 -1(2) . . . . ?
Co1 N1 C4 C3 178.6(13) . . . . ?
C1 N1 C4 C5 179.4(14) . . . . ?
Co1 N1 C4 C5 -1.4(19) . . . . ?
N2 C3 C4 N1 0(3) . . . . ?
N2 C3 C4 C5 -179.9(18) . . . . ?
N3 C5 C4 N1 6(2) . . . . ?
C6 C5 C4 N1 -176.2(18) . . . . ?
N3 C5 C4 C3 -174.4(17) . . . . ?
C6 C5 C4 C3 4(3) . . . . ?
C20 C21 C22 N10 0(3) . . . . ?
C18 N10 C22 C21 1(3) . . . . ?
Co1 N10 C22 C21 178.9(13) . . . . ?
N3 N4 C7 N5 0(2) . . . . ?
N3 N4 C7 C8 176.2(14) . . . . ?
C11 N5 C7 N4 176.5(15) . . . . ?
Co1 N5 C7 N4 -0.7(18) . . . . ?
C11 N5 C7 C8 0(2) . . . . ?
Co1 N5 C7 C8 -177.5(12) . . . . ?
C9 C8 C7 N4 -179.6(17) . . . . ?
C9 C8 C7 N5 -3(2) . . . . ?

_refine_diff_density_max         1.045
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.192

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1571717'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 Cl2 Co N12 O13'
_chemical_formula_weight         830.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.826(4)
_cell_length_b                   13.366(4)
_cell_length_c                   18.433(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.714(7)
_cell_angle_gamma                90
_cell_volume                     3563.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9087
_cell_measurement_theta_min      0.23
_cell_measurement_theta_max      30.32

_exptl_crystal_description       block
_exptl_crystal_colour            dark-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             1692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.710
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21353
_diffrn_reflns_av_unetI/netI     0.1133
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         27.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7822
_reflns_number_gt                3107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1100P)²+7.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7822
_refine_ls_number_parameters     505
_refine_ls_number_restraints     347
_refine_ls_R_factor_all          0.2189
_refine_ls_R_factor_gt           0.1001
_refine_ls_wR_factor_ref         0.3089
_refine_ls_wR_factor_gt          0.2484
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.00749(7) 1.64606(8) 0.20116(5) 0.0632(4) Uani 1 1 d . U . . .
N5 N 1.1396(4) 1.6442(5) 0.1852(3) 0.0683(17) Uani 1 1 d . U . . .
N11 N 1.0567(4) 1.6690(5) 0.3171(3) 0.0620(16) Uani 1 1 d . U . . .
N7 N 0.9467(4) 1.5575(6) 0.1079(3) 0.0729(18) Uani 1 1 d . U . . .
C20 C 1.0595(5) 1.5838(6) 0.3575(4) 0.0653(19) Uani 1 1 d . U . . .
N9 N 0.9996(4) 1.5072(5) 0.2460(4) 0.0705(17) Uani 1 1 d . U . . .
N3 N 1.0144(5) 1.7762(5) 0.1475(4) 0.0752(19) Uani 1 1 d . U . . .
C23 C 1.1207(6) 1.7572(7) 0.4264(4) 0.077(2) Uani 1 1 d . U . . .
N10 N 1.0287(4) 1.4972(5) 0.3219(4) 0.0736(18) Uani 1 1 d . U . . .
C8 C 1.1601(6) 1.7213(7) 0.1449(4) 0.074(2) Uani 1 1 d . U . . .
N4 N 1.0911(5) 1.7918(5) 0.1208(4) 0.0783(19) Uani 1 1 d . U . . .
C16 C 0.9456(6) 1.4598(8) 0.1247(5) 0.084(3) Uani 1 1 d . U . . .
C24 C 1.0868(5) 1.7542(6) 0.3519(4) 0.073(2) Uani 1 1 d . U . . .
H24 H 1.0844 1.8128 0.3244 0.087 Uiso 1 1 calc R U . . .
C21 C 1.0909(6) 1.5870(8) 0.4355(4) 0.084(3) Uani 1 1 d . U . . .
H21 H 1.0897 1.5296 0.4639 0.101 Uiso 1 1 calc R U . . .
C22 C 1.1224(6) 1.6728(8) 0.4683(5) 0.090(3) Uani 1 1 d . U . . .
H22 H 1.1455 1.6751 0.5194 0.108 Uiso 1 1 calc R U . . .
N12 N 1.1594(6) 1.8504(8) 0.4623(5) 0.106(3) Uani 1 1 d . U . . .
C11 C 1.2909(7) 1.5836(8) 0.1945(5) 0.084(3) Uani 1 1 d . U . . .
O4 O 1.1960(6) 1.8487(6) 0.5286(4) 0.143(3) Uani 1 1 d . U . . .
C5 C 0.9474(8) 1.8401(7) 0.1446(5) 0.092(3) Uani 1 1 d . U . . .
C13 C 0.9141(6) 1.5844(8) 0.0374(5) 0.089(3) Uani 1 1 d . U . . .
H13 H 0.9154 1.6510 0.0230 0.107 Uiso 1 1 calc R U . . .
C14 C 0.8775(7) 1.5096(11) -0.0148(6) 0.113(4) Uani 1 1 d . U . . .
H14 H 0.8520 1.5301 -0.0632 0.136 Uiso 1 1 calc R U . . .
N1 N 0.8816(5) 1.7052(7) 0.2008(4) 0.091(2) Uani 1 1 d . U . . .
C12 C 1.2051(6) 1.5755(6) 0.2099(4) 0.076(2) Uani 1 1 d . U . . .
H12 H 1.1920 1.5216 0.2379 0.091 Uiso 1 1 calc R U . . .
C17 C 0.9780(6) 1.4310(7) 0.2039(5) 0.078(2) Uani 1 1 d . U . . .
O3 O 1.1554(7) 1.9248(6) 0.4233(5) 0.140(3) Uani 1 1 d . U . . .
N8 N 0.8765(7) 1.4178(10) -0.0015(6) 0.131(4) Uani 1 1 d . U . . .
C9 C 1.2473(8) 1.7306(8) 0.1280(5) 0.097(3) Uani 1 1 d . U . . .
H9 H 1.2602 1.7839 0.0994 0.116 Uiso 1 1 calc R U . . .
C15 C 0.9098(9) 1.3898(10) 0.0680(7) 0.127(4) Uani 1 1 d . U . . .
H15 H 0.9097 1.3222 0.0800 0.152 Uiso 1 1 calc R U . . .
C4 C 0.8692(7) 1.7968(8) 0.1699(5) 0.094(3) Uani 1 1 d . U . . .
C7 C 1.0977(8) 1.8586(8) 0.0585(6) 0.125(4) Uani 1 1 d . U . . .
H7C H 1.0373 1.8684 0.0275 0.187 Uiso 1 1 calc R U . . .
H7A H 1.1375 1.8290 0.0298 0.187 Uiso 1 1 calc R U . . .
H7B H 1.1227 1.9219 0.0777 0.187 Uiso 1 1 calc R U . . .
C1 C 0.8110(8) 1.6584(10) 0.2229(6) 0.126(4) Uani 1 1 d . U . . .
H1 H 0.8212 1.5963 0.2461 0.151 Uiso 1 1 calc R U . . .
C19 C 0.9864(10) 1.4231(10) 0.3659(7) 0.153(5) Uani 1 1 d . U . . .
H19A H 0.9692 1.4565 0.4069 0.229 Uiso 1 1 calc R U . . .
H19C H 1.0304 1.3714 0.3843 0.229 Uiso 1 1 calc R U . . .
H19B H 0.9325 1.3939 0.3345 0.229 Uiso 1 1 calc R U . . .
C10 C 1.3134(7) 1.6598(8) 0.1544(6) 0.094(3) Uani 1 1 d . U . . .
H10 H 1.3723 1.6644 0.1447 0.113 Uiso 1 1 calc R U . . .
N2 N 0.7139(10) 1.7959(13) 0.1859(8) 0.175(5) Uani 1 1 d . U . . .
C2 C 0.7230(10) 1.7019(15) 0.2114(8) 0.159(5) Uani 1 1 d . U . . .
H2 H 0.6728 1.6669 0.2212 0.191 Uiso 1 1 calc R U . . .
C6 C 0.9420(9) 1.9477(8) 0.1195(7) 0.140(5) Uani 1 1 d . U . . .
H6A H 1.0033 1.9730 0.1223 0.209 Uiso 1 1 calc R U . . .
H6C H 0.9122 1.9868 0.1512 0.209 Uiso 1 1 calc R U . . .
H6B H 0.9071 1.9520 0.0691 0.209 Uiso 1 1 calc R U . . .
C3 C 0.7840(11) 1.8411(11) 0.1628(8) 0.146(5) Uani 1 1 d . U . . .
H3 H 0.7744 1.9043 0.1413 0.175 Uiso 1 1 calc R U . . .
Cl2 Cl 0.8025(2) 1.6448(2) 0.42633(16) 0.1179(10) Uani 1 1 d D U . . .
O2 O 1.3334(7) 1.4326(8) 0.2529(5) 0.146(4) Uani 1 1 d . U . . .
N6 N 1.3602(8) 1.5067(9) 0.2242(5) 0.115(3) Uani 1 1 d . U . . .
O1 O 1.4394(6) 1.5208(9) 0.2174(6) 0.175(4) Uani 1 1 d . U . . .
C18 C 0.9936(11) 1.3250(9) 0.2284(7) 0.159(6) Uani 1 1 d . U . . .
H18A H 0.9352 1.2913 0.2219 0.239 Uiso 1 1 calc R U . . .
H18B H 1.0246 1.3231 0.2799 0.239 Uiso 1 1 calc R U . . .
H18C H 1.0310 1.2923 0.1992 0.239 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1485(2) 0.1830(3) 0.10053(17) 0.1247(11) Uani 1 1 d D U . . .
O7 O 0.1470(12) 0.1860(14) 0.0210(4) 0.149(7) Uani 0.666(14) 1 d D U P A 1
O5 O 0.2164(9) 0.1070(11) 0.1308(6) 0.152(6) Uani 0.666(14) 1 d D U P A 1
O8 O 0.0585(6) 0.1510(10) 0.1118(8) 0.138(5) Uani 0.666(14) 1 d D U P A 1
O6 O 0.1669(12) 0.2806(8) 0.1332(8) 0.164(6) Uani 0.666(14) 1 d D U P A 1
O8A O 0.0538(11) 0.217(3) 0.099(2) 0.27(3) Uiso 0.334(14) 1 d D . P A 2
O7A O 0.173(2) 0.204(3) 0.0293(10) 0.17(2) Uiso 0.334(14) 1 d D . P A 2
O6A O 0.2107(14) 0.2389(18) 0.1601(10) 0.117(9) Uiso 0.334(14) 1 d D . P A 2
O5A O 0.157(3) 0.0760(9) 0.1194(19) 0.25(2) Uiso 0.334(14) 1 d D . P A 2
O12 O 0.8636(10) 1.7003(12) 0.3852(8) 0.201(8) Uani 0.666(14) 1 d D U P A 1
O11 O 0.8035(14) 1.5427(7) 0.4019(10) 0.229(10) Uani 0.666(14) 1 d D U P A 1
O10 O 0.7150(7) 1.6920(12) 0.4095(9) 0.188(8) Uani 0.666(14) 1 d D U P A 1
O9 O 0.8459(11) 1.6581(12) 0.5043(5) 0.197(9) Uani 0.666(14) 1 d D U P A 1
O12A O 0.872(2) 1.587(2) 0.3992(18) 0.202(17) Uiso 0.334(14) 1 d D . P A 2
O11A O 0.839(3) 1.737(2) 0.464(2) 0.48(6) Uiso 0.334(14) 1 d D . P A 2
O10A O 0.7228(16) 1.664(3) 0.3645(14) 0.27(3) Uiso 0.334(14) 1 d D . P A 2
O9A O 0.7651(16) 1.5798(17) 0.4782(13) 0.147(11) Uiso 0.334(14) 1 d D . P A 2
O13 O 0.8865(19) 1.931(2) 0.4064(15) 0.415(13) Uiso 1 1 d D . . . .
C25 C 0.810(2) 1.949(2) 0.3437(17) 0.330(14) Uiso 1 1 d 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 N3 2.014(7) . ?
Co1 N1 2.026(7) . ?
Co1 N5 2.044(7) . ?
Co1 N9 2.046(7) . ?
Co1 N7 2.117(6) . ?
Co1 N11 2.123(6) . ?
N5 C12 1.342(9) . ?
N5 C8 1.343(10) . ?
N11 C24 1.335(9) . ?
N11 C20 1.356(9) . ?
N7 C13 1.332(10) . ?
N7 C16 1.344(11) . ?
C20 N10 1.360(10) . ?
C20 C21 1.412(10) . ?
N9 C17 1.277(9) . ?
N9 N10 1.377(9) . ?
N3 C5 1.303(11) . ?
N3 N4 1.351(9) . ?
C23 C24 1.355(10) . ?
C23 C22 1.364(12) . ?
C23 N12 1.467(11) . ?
N10 C19 1.501(12) . ?
C8 N4 1.389(10) . ?
C8 C9 1.401(12) . ?
N4 C7 1.475(11) . ?
C16 C15 1.415(13) . ?
C16 C17 1.485(12) . ?
C24 H24 0.9300 . ?
C21 C22 1.331(12) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N12 O3 1.221(10) . ?
N12 O4 1.223(10) . ?
C11 C10 1.344(13) . ?
C11 C12 1.367(12) . ?
C11 N6 1.471(13) . ?
C5 C4 1.462(14) . ?
C5 C6 1.508(13) . ?
C13 C14 1.412(13) . ?
C13 H13 0.9300 . ?
C14 N8 1.251(14) . ?
C14 H14 0.9300 . ?
N1 C4 1.346(12) . ?
N1 C1 1.357(13) . ?
C12 H12 0.9300 . ?
C17 C18 1.490(14) . ?
N8 C15 1.322(15) . ?
C9 C10 1.372(13) . ?
C9 H9 0.9300 . ?
C15 H15 0.9300 . ?
C4 C3 1.374(16) . ?
C7 H7C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C1 C2 1.402(16) . ?
C1 H1 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
C10 H10 0.9300 . ?
N2 C2 1.337(18) . ?
N2 C3 1.350(18) . ?
C2 H2 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6C 0.9600 . ?
C6 H6B 0.9600 . ?
C3 H3 0.9300 . ?
Cl2 O10 1.415(7) . ?
Cl2 O11 1.438(8) . ?
Cl2 O9 1.450(7) . ?
Cl2 O12A 1.461(9) . ?
Cl2 O11A 1.462(9) . ?
Cl2 O10A 1.474(9) . ?
Cl2 O9A 1.487(9) . ?
Cl2 O12 1.499(8) . ?
O2 N6 1.229(12) . ?
N6 O1 1.223(13) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
Cl1 O6 1.437(7) . ?
Cl1 O5 1.452(7) . ?
Cl1 O8 1.459(7) . ?
Cl1 O7 1.462(7) . ?
Cl1 O7A 1.465(9) . ?
Cl1 O5A 1.471(9) . ?
Cl1 O6A 1.472(9) . ?
Cl1 O8A 1.473(9) . ?
O13 C25 1.449(10) . ?

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
N3 Co1 N1 78.9(4) . . ?
N3 Co1 N5 77.6(3) . . ?
N1 Co1 N5 156.3(3) . . ?
N3 Co1 N9 174.5(3) . . ?
N1 Co1 N9 102.8(3) . . ?
N5 Co1 N9 100.9(3) . . ?
N3 Co1 N7 98.2(3) . . ?
N1 Co1 N7 89.3(3) . . ?
N5 Co1 N7 97.3(2) . . ?
N9 Co1 N7 76.6(3) . . ?
N3 Co1 N11 109.0(2) . . ?
N1 Co1 N11 93.4(2) . . ?
N5 Co1 N11 91.1(2) . . ?
N9 Co1 N11 76.2(2) . . ?
N7 Co1 N11 152.7(3) . . ?
C12 N5 C8 118.6(8) . . ?
C12 N5 Co1 127.1(6) . . ?
C8 N5 Co1 114.3(5) . . ?
C24 N11 C20 119.1(6) . . ?
C24 N11 Co1 127.7(5) . . ?
C20 N11 Co1 113.2(5) . . ?
C13 N7 C16 117.8(7) . . ?
C13 N7 Co1 129.7(6) . . ?
C16 N7 Co1 112.4(5) . . ?
N11 C20 N10 119.0(7) . . ?
N11 C20 C21 119.8(8) . . ?
N10 C20 C21 121.2(8) . . ?
C17 N9 N10 121.3(7) . . ?
C17 N9 Co1 120.5(6) . . ?
N10 N9 Co1 117.8(5) . . ?
C5 N3 N4 125.4(8) . . ?
C5 N3 Co1 117.8(7) . . ?
N4 N3 Co1 116.7(5) . . ?
C24 C23 C22 120.3(8) . . ?
C24 C23 N12 120.2(8) . . ?
C22 C23 N12 119.4(8) . . ?
C20 N10 N9 113.8(6) . . ?
C20 N10 C19 115.9(8) . . ?
N9 N10 C19 122.6(7) . . ?
N5 C8 N4 117.2(8) . . ?
N5 C8 C9 121.5(8) . . ?
N4 C8 C9 121.3(9) . . ?
N3 N4 C8 113.5(7) . . ?
N3 N4 C7 125.6(8) . . ?
C8 N4 C7 119.3(9) . . ?
N7 C16 C15 119.7(10) . . ?
N7 C16 C17 117.4(7) . . ?
C15 C16 C17 122.9(10) . . ?
N11 C24 C23 121.5(8) . . ?
N11 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C22 C21 C20 119.5(8) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 119.7(8) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
O3 N12 O4 123.9(9) . . ?
O3 N12 C23 117.6(8) . . ?
O4 N12 C23 118.5(10) . . ?
C10 C11 C12 122.0(9) . . ?
C10 C11 N6 119.7(11) . . ?
C12 C11 N6 118.2(11) . . ?
N3 C5 C4 112.2(9) . . ?
N3 C5 C6 128.8(11) . . ?
C4 C5 C6 118.9(10) . . ?
N7 C13 C14 118.4(10) . . ?
N7 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
N8 C14 C13 125.5(11) . . ?
N8 C14 H14 117.3 . . ?
C13 C14 H14 117.3 . . ?
C4 N1 C1 120.2(9) . . ?
C4 N1 Co1 113.4(7) . . ?
C1 N1 Co1 126.2(8) . . ?
N5 C12 C11 120.8(9) . . ?
N5 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
N9 C17 C16 112.0(8) . . ?
N9 C17 C18 125.0(9) . . ?
C16 C17 C18 122.6(9) . . ?
C14 N8 C15 116.8(11) . . ?
C10 C9 C8 118.9(10) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N8 C15 C16 121.8(12) . . ?
N8 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
N1 C4 C3 118.1(13) . . ?
N1 C4 C5 116.8(8) . . ?
C3 C4 C5 125.1(12) . . ?
N4 C7 H7C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C1 C2 121.2(13) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
N10 C19 H19A 109.5 . . ?
N10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
N10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
C11 C10 C9 118.2(10) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C2 N2 C3 120.5(14) . . ?
N2 C2 C1 117.4(15) . . ?
N2 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
N2 C3 C4 122.1(14) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O10 Cl2 O11 115.2(10) . . ?
O10 Cl2 O9 110.4(9) . . ?
O11 Cl2 O9 113.2(9) . . ?
O12A Cl2 O11A 112.6(13) . . ?
O12A Cl2 O10A 109.7(13) . . ?
O11A Cl2 O10A 111.5(13) . . ?
O12A Cl2 O9A 107.8(12) . . ?
O11A Cl2 O9A 110.4(13) . . ?
O10A Cl2 O9A 104.6(12) . . ?
O10 Cl2 O12 107.2(9) . . ?
O11 Cl2 O12 105.2(9) . . ?
O9 Cl2 O12 104.7(8) . . ?
O1 N6 O2 125.2(12) . . ?
O1 N6 C11 117.6(13) . . ?
O2 N6 C11 117.2(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 Cl1 O5 115.0(8) . . ?
O6 Cl1 O8 107.5(8) . . ?
O5 Cl1 O8 108.6(7) . . ?
O6 Cl1 O7 110.8(9) . . ?
O5 Cl1 O7 105.1(7) . . ?
O8 Cl1 O7 109.8(8) . . ?
O7A Cl1 O5A 111.7(13) . . ?
O7A Cl1 O6A 109.5(12) . . ?
O5A Cl1 O6A 108.0(12) . . ?
O7A Cl1 O8A 110.4(13) . . ?
O5A Cl1 O8A 110.0(13) . . ?
O6A Cl1 O8A 107.1(12) . . ?

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.101

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1571716'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Cl0 Co N8 O2'
_chemical_formula_weight         537.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

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

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

_cell_length_a                   12.408(2)
_cell_length_b                   19.368(3)
_cell_length_c                   9.8080(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2357.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5143
_cell_measurement_theta_min      0.33
_cell_measurement_theta_max      30.12

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.771
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6140
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2054
_reflns_number_gt                2004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.976

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+4.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2054
_refine_ls_number_parameters     170
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.03585(17) 0.0272(4) Uani 1 2 d S T P . .
O1 O 0.5026(3) 0.4138(3) 0.1639(6) 0.0388(13) Uani 1 1 d . . . . .
N3 N 0.3424(4) 0.4696(3) 0.0501(6) 0.0290(11) Uani 1 1 d . . . . .
N4 N 0.3156(4) 0.4185(3) 0.1430(6) 0.0323(12) Uani 1 1 d . . . . .
N1 N 0.4190(4) 0.5579(3) -0.1225(6) 0.0310(11) Uani 1 1 d . . . . .
N2 N 0.2897(6) 0.6283(3) -0.3044(8) 0.0567(19) Uani 1 1 d . . . . .
C7 C 0.4078(5) 0.3921(3) 0.1937(7) 0.0290(13) Uani 1 1 d . . . . .
C5 C 0.2676(6) 0.5001(3) -0.0213(9) 0.0361(17) Uani 1 1 d . . . . .
C8 C 0.3946(5) 0.3358(3) 0.2929(7) 0.0319(14) Uani 1 1 d . . . . .
C4 C 0.3101(5) 0.5483(3) -0.1203(7) 0.0310(14) Uani 1 1 d . . . . .
C11 C 0.3765(8) 0.2305(4) 0.4902(8) 0.053(2) Uani 1 1 d . . . . .
H11 H 0.3705 0.1955 0.5548 0.064 Uiso 1 1 calc R U . . .
C9 C 0.2942(7) 0.3142(4) 0.3428(11) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.2316 0.3342 0.3087 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2464(8) 0.5857(3) -0.2135(10) 0.0457(17) Uani 1 1 d . . . . .
H3 H 0.1719 0.5805 -0.2112 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4603(7) 0.5987(4) -0.2144(8) 0.0396(15) Uani 1 1 d . . . . .
H1 H 0.5348 0.6028 -0.2194 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4851(6) 0.3009(5) 0.3427(9) 0.0437(18) Uani 1 1 d . . . . .
H13 H 0.5531 0.3119 0.3094 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4745(7) 0.2505(5) 0.4402(9) 0.049(2) Uani 1 1 d . . . . .
H12 H 0.5363 0.2292 0.4735 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3973(8) 0.6365(4) -0.3053(9) 0.057(2) Uani 1 1 d . . . . .
H2 H 0.4294 0.6671 -0.3661 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1502(6) 0.4831(5) -0.0042(9) 0.047(2) Uani 1 1 d . . . . .
H5B H 0.1399 0.4343 -0.0149 0.070 Uiso 1 1 calc R U . . .
H5A H 0.1089 0.5073 -0.0718 0.070 Uiso 1 1 calc R U . . .
H5C H 0.1269 0.4969 0.0851 0.070 Uiso 1 1 calc R U . . .
C10 C 0.2873(8) 0.2643(5) 0.4408(12) 0.073(3) Uani 1 1 d . . . . .
H10 H 0.2198 0.2528 0.4754 0.087 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 N3 2.047(5) 2_665 ?
Co1 N3 2.047(5) . ?
Co1 O1 2.089(6) . ?
Co1 O1 2.089(6) 2_665 ?
Co1 N1 2.163(5) 2_665 ?
Co1 N1 2.163(5) . ?
O1 C7 1.282(7) . ?
N3 C5 1.304(10) . ?
N3 N4 1.387(8) . ?
N4 C7 1.347(8) . ?
N1 C1 1.304(9) . ?
N1 C4 1.364(9) . ?
N2 C3 1.328(12) . ?
N2 C2 1.344(13) . ?
C7 C8 1.472(9) . ?
C5 C4 1.446(11) . ?
C5 C6 1.502(11) . ?
C8 C9 1.401(10) . ?
C8 C13 1.398(10) . ?
C4 C3 1.410(10) . ?
C11 C12 1.367(12) . ?
C11 C10 1.374(13) . ?
C11 H11 0.9300 . ?
C9 C10 1.367(13) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C1 C2 1.393(11) . ?
C1 H1 0.9300 . ?
C13 C12 1.372(12) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C6 H5B 0.9600 . ?
C6 H5A 0.9600 . ?
C6 H5C 0.9600 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Co1 N3 172.2(3) 2_665 . ?
N3 Co1 O1 100.03(19) 2_665 . ?
N3 Co1 O1 75.17(18) . . ?
N3 Co1 O1 75.17(18) 2_665 2_665 ?
N3 Co1 O1 100.03(19) . 2_665 ?
O1 Co1 O1 106.1(4) . 2_665 ?
N3 Co1 N1 75.8(2) 2_665 2_665 ?
N3 Co1 N1 110.1(2) . 2_665 ?
O1 Co1 N1 90.6(2) . 2_665 ?
O1 Co1 N1 148.52(18) 2_665 2_665 ?
N3 Co1 N1 110.1(2) 2_665 . ?
N3 Co1 N1 75.8(2) . . ?
O1 Co1 N1 148.52(18) . . ?
O1 Co1 N1 90.6(2) 2_665 . ?
N1 Co1 N1 88.2(3) 2_665 . ?
C7 O1 Co1 112.6(4) . . ?
C5 N3 N4 120.4(6) . . ?
C5 N3 Co1 120.9(5) . . ?
N4 N3 Co1 118.6(4) . . ?
C7 N4 N3 108.0(5) . . ?
C1 N1 C4 118.9(6) . . ?
C1 N1 Co1 128.9(5) . . ?
C4 N1 Co1 112.2(4) . . ?
C3 N2 C2 118.7(7) . . ?
O1 C7 N4 124.8(6) . . ?
O1 C7 C8 119.7(6) . . ?
N4 C7 C8 115.5(5) . . ?
N3 C5 C4 113.1(7) . . ?
N3 C5 C6 122.1(7) . . ?
C4 C5 C6 124.7(7) . . ?
C9 C8 C13 116.6(7) . . ?
C9 C8 C7 123.4(6) . . ?
C13 C8 C7 120.0(6) . . ?
N1 C4 C3 118.3(7) . . ?
N1 C4 C5 117.4(6) . . ?
C3 C4 C5 124.3(7) . . ?
C12 C11 C10 117.0(7) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C10 C9 C8 120.8(8) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N2 C3 C4 121.9(8) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C1 C2 122.7(8) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C12 C13 C8 120.7(7) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C11 C12 C13 122.5(8) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
N2 C2 C1 119.4(8) . . ?
N2 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C5 C6 H5B 109.5 . . ?
C5 C6 H5A 109.5 . . ?
H5B C6 H5A 109.5 . . ?
C5 C6 H5C 109.5 . . ?
H5B C6 H5C 109.5 . . ?
H5A C6 H5C 109.5 . . ?
C11 C10 C9 122.3(8) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N3 N4 C7 175.0(6) . . . . ?
Co1 N3 N4 C7 -8.6(7) . . . . ?
Co1 O1 C7 N4 3.8(9) . . . . ?
Co1 O1 C7 C8 -174.4(4) . . . . ?
N3 N4 C7 O1 2.9(9) . . . . ?
N3 N4 C7 C8 -178.9(5) . . . . ?
N4 N3 C5 C4 -175.6(5) . . . . ?
Co1 N3 C5 C4 8.1(8) . . . . ?
N4 N3 C5 C6 1.7(10) . . . . ?
Co1 N3 C5 C6 -174.6(5) . . . . ?
O1 C7 C8 C9 172.6(8) . . . . ?
N4 C7 C8 C9 -5.8(10) . . . . ?
O1 C7 C8 C13 -7.2(9) . . . . ?
N4 C7 C8 C13 174.5(7) . . . . ?
C1 N1 C4 C3 -3.1(9) . . . . ?
Co1 N1 C4 C3 176.8(5) . . . . ?
C1 N1 C4 C5 177.1(6) . . . . ?
Co1 N1 C4 C5 -3.0(7) . . . . ?
N3 C5 C4 N1 -2.8(8) . . . . ?
C6 C5 C4 N1 180.0(6) . . . . ?
N3 C5 C4 C3 177.4(6) . . . . ?
C6 C5 C4 C3 0.2(10) . . . . ?
C13 C8 C9 C10 3.6(13) . . . . ?
C7 C8 C9 C10 -176.1(8) . . . . ?
C2 N2 C3 C4 -1.2(11) . . . . ?
N1 C4 C3 N2 1.7(10) . . . . ?
C5 C4 C3 N2 -178.5(7) . . . . ?
C4 N1 C1 C2 4.1(11) . . . . ?
Co1 N1 C1 C2 -175.7(6) . . . . ?
C9 C8 C13 C12 -3.0(12) . . . . ?
C7 C8 C13 C12 176.8(7) . . . . ?
C10 C11 C12 C13 -1.5(13) . . . . ?
C8 C13 C12 C11 2.0(14) . . . . ?
C3 N2 C2 C1 2.1(13) . . . . ?
N1 C1 C2 N2 -3.6(13) . . . . ?
C12 C11 C10 C9 2.2(15) . . . . ?
C8 C9 C10 C11 -3.3(16) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

