# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_mm264a
_database_code_depnum_ccdc_archive 'CCDC 994355'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 Cl Co N10 O11.50'
_chemical_formula_weight         685.89

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/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                   11.727(3)
_cell_length_b                   24.744(6)
_cell_length_c                   9.764(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.883(5)
_cell_angle_gamma                90
_cell_volume                     2799.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1838
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.61

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             1412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.787
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14262
_diffrn_reflns_av_unetI/netI     0.1078
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         23.381
_diffrn_reflns_theta_full        23.381
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4029
_reflns_number_gt                2414
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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)+(0.0663P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4029
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.56196(7) 0.86803(3) 0.30342(8) 0.0220(3) Uani 1 1 d . . . . .
Cl1 Cl 0.04229(18) 0.75832(8) -0.0897(2) 0.0600(6) Uani 1 1 d . . . . .
O1 O 0.6373(3) 0.72113(15) 0.4625(4) 0.0302(10) Uani 1 1 d . . . . .
O2 O 0.4895(3) 0.71403(15) 0.2013(4) 0.0292(10) Uani 1 1 d . . . . .
O3 O 0.6577(4) 1.01157(17) 0.1735(5) 0.0531(14) Uani 1 1 d . . . . .
O4 O 0.4635(4) 1.02229(16) 0.3177(5) 0.0425(12) Uani 1 1 d . . . . .
O5 O 0.1832(4) 0.80088(19) 0.1977(5) 0.0548(14) Uani 1 1 d . . . . .
H5B H 0.1428 0.7898 0.1096 0.082 Uiso 1 1 d R U . . .
H5C H 0.1404 0.7888 0.2739 0.082 Uiso 1 1 d R U . . .
O6 O 0.1852(4) 0.9144(2) 0.1738(5) 0.0585(15) Uani 1 1 d . . . . .
H6A H 0.1534 0.9211 0.0793 0.088 Uiso 1 1 d R U . . .
H6B H 0.1702 0.8760 0.1995 0.088 Uiso 1 1 d R U . . .
O7 O 0.0979(4) 0.95366(18) -0.0956(5) 0.0580(14) Uani 1 1 d . . . . .
H7A H 0.1624 0.9617 -0.1197 0.087 Uiso 1 1 d R U . . .
H7B H 0.0783 0.9248 -0.1401 0.087 Uiso 1 1 d R U . . .
O8 O 0.0819(4) 0.8618(2) -0.2605(5) 0.0647(15) Uani 1 1 d . . . . .
H8B H 0.0281 0.8370 -0.2311 0.097 Uiso 1 1 d R U . . .
H8C H 0.0551 0.8734 -0.3587 0.097 Uiso 1 1 d R U . . .
O9 O -0.0523(5) 0.8534(2) -0.5119(6) 0.091(2) Uani 1 1 d . . . . .
H9B H -0.0613 0.8848 -0.5694 0.136 Uiso 1 1 d R U . . .
H9C H -0.0584 0.8198 -0.5703 0.136 Uiso 1 1 d R U . . .
O10 O 0.0643(5) 0.9944(2) 0.2953(5) 0.0706(16) Uani 1 1 d . . . . .
H10B H 0.1193 0.9681 0.2761 0.106 Uiso 1 1 d R U . . .
H10C H -0.0004 0.9973 0.2153 0.106 Uiso 1 1 d R U . . .
O11 O -0.1089(5) 0.9562(2) 0.4344(6) 0.0865(19) Uani 1 1 d . . . . .
H11A H -0.0510 0.9686 0.3830 0.130 Uiso 1 1 d R U . . .
H11B H -0.0970 0.9727 0.5296 0.130 Uiso 1 1 d R U . . .
O12 O 0.5976(7) 0.8936(3) -0.1049(8) 0.036(2) Uani 0.5 1 d . . P . .
H12A H 0.6746 0.9073 -0.0869 0.054 Uiso 0.5 1 d R U P . .
H12B H 0.5488 0.9165 -0.1760 0.054 Uiso 0.5 1 d R U P . .
N1 N 0.5588(4) 0.79179(17) 0.3205(4) 0.0206(11) Uani 1 1 d . . . . .
N2 N 0.6564(4) 0.86383(17) 0.4833(4) 0.0204(11) Uani 1 1 d . . . . .
N3 N 0.7423(4) 0.79896(18) 0.6482(5) 0.0290(13) Uani 1 1 d . . . . .
N4 N 0.4630(4) 0.85362(17) 0.1282(5) 0.0210(12) Uani 1 1 d . . . . .
N5 N 0.3754(4) 0.78057(18) -0.0055(5) 0.0251(12) Uani 1 1 d . . . . .
N6 N 0.5648(4) 0.94385(18) 0.2807(5) 0.0256(12) Uani 1 1 d . . . . .
N7 N 0.6991(4) 0.87086(19) 0.2152(4) 0.0258(12) Uani 1 1 d . . . . .
N8 N 0.8125(5) 0.9331(2) 0.1106(5) 0.0377(14) Uani 1 1 d . . . . .
N9 N 0.4300(4) 0.88413(17) 0.3924(4) 0.0208(12) Uani 1 1 d . . . . .
N10 N 0.3230(4) 0.9586(2) 0.4589(5) 0.0327(13) Uani 1 1 d . . . . .
C1 C 0.6229(5) 0.7689(2) 0.4349(6) 0.0209(14) Uani 1 1 d . . . . .
C2 C 0.6799(5) 0.8127(2) 0.5295(6) 0.0197(14) Uani 1 1 d . . . . .
C3 C 0.7016(5) 0.9039(2) 0.5677(6) 0.0302(16) Uani 1 1 d . . . . .
H3A H 0.6893 0.9405 0.5394 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7655(6) 0.8924(3) 0.6941(7) 0.0377(17) Uani 1 1 d . . . . .
H4A H 0.7947 0.9207 0.7554 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7865(6) 0.8392(3) 0.7310(7) 0.0387(18) Uani 1 1 d . . . . .
H5A H 0.8333 0.8309 0.8168 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4981(5) 0.7629(2) 0.2128(6) 0.0198(13) Uani 1 1 d . . . . .
C7 C 0.4403(5) 0.8005(2) 0.1046(6) 0.0223(14) Uani 1 1 d . . . . .
C8 C 0.4156(6) 0.8887(2) 0.0308(6) 0.0390(18) Uani 1 1 d . . . . .
H8A H 0.4299 0.9263 0.0428 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3467(6) 0.8701(3) -0.0859(6) 0.0436(19) Uani 1 1 d . . . . .
H9A H 0.3124 0.8947 -0.1549 0.052 Uiso 1 1 calc R U . . .
C10 C 0.3276(5) 0.8158(2) -0.1022(6) 0.0321(16) Uani 1 1 d . . . . .
H10A H 0.2799 0.8028 -0.1830 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6450(6) 0.9652(2) 0.2087(7) 0.0350(17) Uani 1 1 d . . . . .
C12 C 0.7257(6) 0.9208(2) 0.1737(6) 0.0272(15) Uani 1 1 d . . . . .
C13 C 0.7717(6) 0.8304(2) 0.1922(6) 0.0305(16) Uani 1 1 d . . . . .
H13A H 0.7576 0.7947 0.2214 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8645(5) 0.8402(3) 0.1276(6) 0.0315(16) Uani 1 1 d . . . . .
H14A H 0.9155 0.8119 0.1112 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8820(6) 0.8921(3) 0.0870(6) 0.0374(17) Uani 1 1 d . . . . .
H15A H 0.9457 0.8995 0.0405 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4800(5) 0.9742(2) 0.3273(6) 0.0279(15) Uani 1 1 d . . . . .
C17 C 0.4040(5) 0.9377(2) 0.3986(6) 0.0243(15) Uani 1 1 d . . . . .
C18 C 0.3618(5) 0.8499(2) 0.4503(6) 0.0265(15) Uani 1 1 d . . . . .
H18A H 0.3750 0.8121 0.4464 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2732(5) 0.8687(3) 0.5148(6) 0.0309(15) Uani 1 1 d . . . . .
H19A H 0.2247 0.8446 0.5551 0.037 Uiso 1 1 calc R U . . .
C20 C 0.2581(6) 0.9235(3) 0.5186(6) 0.0352(17) Uani 1 1 d . . . . .
H20A H 0.1991 0.9373 0.5654 0.042 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 N6 1.890(4) . ?
Co1 N1 1.895(4) . ?
Co1 N2 1.929(5) . ?
Co1 N9 1.930(5) . ?
Co1 N7 1.940(5) . ?
Co1 N4 1.947(5) . ?
O1 C1 1.219(6) . ?
O2 C6 1.216(6) . ?
O3 C11 1.215(7) . ?
O4 C16 1.206(6) . ?
N1 C1 1.369(7) . ?
N1 C6 1.376(7) . ?
N2 C3 1.345(7) . ?
N2 C2 1.357(6) . ?
N3 C2 1.316(7) . ?
N3 C5 1.335(7) . ?
N4 C8 1.342(7) . ?
N4 C7 1.354(6) . ?
N5 C7 1.313(7) . ?
N5 C10 1.342(7) . ?
N6 C11 1.364(8) . ?
N6 C16 1.379(7) . ?
N7 C12 1.352(7) . ?
N7 C13 1.355(7) . ?
N8 C12 1.304(7) . ?
N8 C15 1.342(8) . ?
N9 C18 1.347(7) . ?
N9 C17 1.363(7) . ?
N10 C17 1.301(7) . ?
N10 C20 1.345(8) . ?
C1 C2 1.510(7) . ?
C3 C4 1.371(8) . ?
C4 C5 1.378(8) . ?
C6 C7 1.490(8) . ?
C8 C9 1.372(8) . ?
C9 C10 1.366(8) . ?
C11 C12 1.522(9) . ?
C13 C14 1.361(8) . ?
C14 C15 1.371(8) . ?
C16 C17 1.512(8) . ?
C18 C19 1.375(8) . ?
C19 C20 1.368(8) . ?

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
N6 Co1 N1 178.33(19) . . ?
N6 Co1 N2 98.18(19) . . ?
N1 Co1 N2 83.26(19) . . ?
N6 Co1 N9 83.0(2) . . ?
N1 Co1 N9 97.91(19) . . ?
N2 Co1 N9 89.36(18) . . ?
N6 Co1 N7 83.2(2) . . ?
N1 Co1 N7 96.0(2) . . ?
N2 Co1 N7 90.42(19) . . ?
N9 Co1 N7 165.99(19) . . ?
N6 Co1 N4 95.60(19) . . ?
N1 Co1 N4 82.98(19) . . ?
N2 Co1 N4 166.18(18) . . ?
N9 Co1 N4 91.29(19) . . ?
N7 Co1 N4 92.25(19) . . ?
C1 N1 C6 124.2(5) . . ?
C1 N1 Co1 117.9(4) . . ?
C6 N1 Co1 117.8(4) . . ?
C3 N2 C2 116.3(5) . . ?
C3 N2 Co1 129.4(4) . . ?
C2 N2 Co1 114.3(4) . . ?
C2 N3 C5 116.9(5) . . ?
C8 N4 C7 117.3(5) . . ?
C8 N4 Co1 129.0(4) . . ?
C7 N4 Co1 113.7(4) . . ?
C7 N5 C10 117.3(5) . . ?
C11 N6 C16 123.3(5) . . ?
C11 N6 Co1 118.0(4) . . ?
C16 N6 Co1 118.4(4) . . ?
C12 N7 C13 116.5(5) . . ?
C12 N7 Co1 114.3(4) . . ?
C13 N7 Co1 129.2(4) . . ?
C12 N8 C15 116.4(6) . . ?
C18 N9 C17 116.1(5) . . ?
C18 N9 Co1 129.0(4) . . ?
C17 N9 Co1 114.9(4) . . ?
C17 N10 C20 116.1(5) . . ?
O1 C1 N1 128.4(5) . . ?
O1 C1 C2 121.8(5) . . ?
N1 C1 C2 109.8(5) . . ?
N3 C2 N2 126.1(5) . . ?
N3 C2 C1 119.2(5) . . ?
N2 C2 C1 114.6(5) . . ?
N2 C3 C4 120.5(6) . . ?
C3 C4 C5 118.9(6) . . ?
N3 C5 C4 121.2(6) . . ?
O2 C6 N1 127.8(5) . . ?
O2 C6 C7 122.2(5) . . ?
N1 C6 C7 110.0(5) . . ?
N5 C7 N4 125.2(5) . . ?
N5 C7 C6 119.2(5) . . ?
N4 C7 C6 115.5(5) . . ?
N4 C8 C9 119.8(6) . . ?
C10 C9 C8 119.5(6) . . ?
N5 C10 C9 120.9(6) . . ?
O3 C11 N6 129.5(6) . . ?
O3 C11 C12 120.7(6) . . ?
N6 C11 C12 109.8(5) . . ?
N8 C12 N7 125.9(6) . . ?
N8 C12 C11 119.7(5) . . ?
N7 C12 C11 114.3(6) . . ?
N7 C13 C14 120.9(6) . . ?
C13 C14 C15 117.8(6) . . ?
N8 C15 C14 122.4(6) . . ?
O4 C16 N6 128.8(6) . . ?
O4 C16 C17 121.8(6) . . ?
N6 C16 C17 109.4(5) . . ?
N10 C17 N9 126.2(5) . . ?
N10 C17 C16 119.6(5) . . ?
N9 C17 C16 114.2(5) . . ?
N9 C18 C19 121.3(5) . . ?
C20 C19 C18 117.2(6) . . ?
N10 C20 C19 123.0(6) . . ?

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
N2 Co1 N1 C1 -3.6(4) . . . . ?
N9 Co1 N1 C1 -92.0(4) . . . . ?
N7 Co1 N1 C1 86.1(4) . . . . ?
N4 Co1 N1 C1 177.6(4) . . . . ?
N2 Co1 N1 C6 -179.5(4) . . . . ?
N9 Co1 N1 C6 92.1(4) . . . . ?
N7 Co1 N1 C6 -89.8(4) . . . . ?
N4 Co1 N1 C6 1.7(4) . . . . ?
N2 Co1 N6 C11 95.2(4) . . . . ?
N9 Co1 N6 C11 -176.5(4) . . . . ?
N7 Co1 N6 C11 5.7(4) . . . . ?
N4 Co1 N6 C11 -85.9(4) . . . . ?
N2 Co1 N6 C16 -90.2(4) . . . . ?
N9 Co1 N6 C16 -1.9(4) . . . . ?
N7 Co1 N6 C16 -179.6(4) . . . . ?
N4 Co1 N6 C16 88.8(4) . . . . ?
C6 N1 C1 O1 -0.5(9) . . . . ?
Co1 N1 C1 O1 -176.1(5) . . . . ?
C6 N1 C1 C2 178.5(5) . . . . ?
Co1 N1 C1 C2 2.9(6) . . . . ?
C5 N3 C2 N2 0.0(9) . . . . ?
C5 N3 C2 C1 -177.0(5) . . . . ?
C3 N2 C2 N3 0.0(8) . . . . ?
Co1 N2 C2 N3 179.9(5) . . . . ?
C3 N2 C2 C1 177.2(5) . . . . ?
Co1 N2 C2 C1 -2.9(6) . . . . ?
O1 C1 C2 N3 -3.4(8) . . . . ?
N1 C1 C2 N3 177.5(5) . . . . ?
O1 C1 C2 N2 179.2(5) . . . . ?
N1 C1 C2 N2 0.1(6) . . . . ?
C2 N2 C3 C4 -1.4(8) . . . . ?
Co1 N2 C3 C4 178.8(5) . . . . ?
N2 C3 C4 C5 2.6(10) . . . . ?
C2 N3 C5 C4 1.3(9) . . . . ?
C3 C4 C5 N3 -2.6(10) . . . . ?
C1 N1 C6 O2 1.2(9) . . . . ?
Co1 N1 C6 O2 176.8(5) . . . . ?
C1 N1 C6 C7 -178.9(5) . . . . ?
Co1 N1 C6 C7 -3.3(6) . . . . ?
C10 N5 C7 N4 -0.2(8) . . . . ?
C10 N5 C7 C6 -178.1(5) . . . . ?
C8 N4 C7 N5 -0.3(8) . . . . ?
Co1 N4 C7 N5 179.6(4) . . . . ?
C8 N4 C7 C6 177.8(5) . . . . ?
Co1 N4 C7 C6 -2.3(6) . . . . ?
O2 C6 C7 N5 1.7(8) . . . . ?
N1 C6 C7 N5 -178.3(5) . . . . ?
O2 C6 C7 N4 -176.5(5) . . . . ?
N1 C6 C7 N4 3.6(7) . . . . ?
C7 N4 C8 C9 0.6(9) . . . . ?
Co1 N4 C8 C9 -179.3(5) . . . . ?
N4 C8 C9 C10 -0.5(10) . . . . ?
C7 N5 C10 C9 0.3(9) . . . . ?
C8 C9 C10 N5 0.0(10) . . . . ?
C16 N6 C11 O3 0.1(10) . . . . ?
Co1 N6 C11 O3 174.4(6) . . . . ?
C16 N6 C11 C12 179.8(5) . . . . ?
Co1 N6 C11 C12 -5.8(6) . . . . ?
C15 N8 C12 N7 -0.9(9) . . . . ?
C15 N8 C12 C11 178.0(5) . . . . ?
C13 N7 C12 N8 1.9(9) . . . . ?
Co1 N7 C12 N8 -179.1(5) . . . . ?
C13 N7 C12 C11 -177.0(5) . . . . ?
Co1 N7 C12 C11 2.0(6) . . . . ?
O3 C11 C12 N8 3.1(9) . . . . ?
N6 C11 C12 N8 -176.7(5) . . . . ?
O3 C11 C12 N7 -177.9(6) . . . . ?
N6 C11 C12 N7 2.3(7) . . . . ?
C12 N7 C13 C14 -1.4(8) . . . . ?
Co1 N7 C13 C14 179.8(4) . . . . ?
N7 C13 C14 C15 0.0(9) . . . . ?
C12 N8 C15 C14 -0.6(9) . . . . ?
C13 C14 C15 N8 1.0(9) . . . . ?
C11 N6 C16 O4 -2.2(10) . . . . ?
Co1 N6 C16 O4 -176.6(5) . . . . ?
C11 N6 C16 C17 178.2(5) . . . . ?
Co1 N6 C16 C17 3.8(6) . . . . ?
C20 N10 C17 N9 -1.1(9) . . . . ?
C20 N10 C17 C16 179.2(5) . . . . ?
C18 N9 C17 N10 2.6(8) . . . . ?
Co1 N9 C17 N10 -176.5(5) . . . . ?
C18 N9 C17 C16 -177.7(5) . . . . ?
Co1 N9 C17 C16 3.2(6) . . . . ?
O4 C16 C17 N10 -4.4(9) . . . . ?
N6 C16 C17 N10 175.3(5) . . . . ?
O4 C16 C17 N9 175.9(5) . . . . ?
N6 C16 C17 N9 -4.4(7) . . . . ?
C17 N9 C18 C19 -1.7(8) . . . . ?
Co1 N9 C18 C19 177.3(4) . . . . ?
N9 C18 C19 C20 -0.5(9) . . . . ?
C17 N10 C20 C19 -1.3(9) . . . . ?
C18 C19 C20 N10 2.1(9) . . . . ?

_refine_diff_density_max         0.701
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_mm247a
_database_code_depnum_ccdc_archive 'CCDC 994356'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 Br Co N10 O11.50'
_chemical_formula_weight         730.35

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.7712(5)
_cell_length_b                   24.6598(11)
_cell_length_c                   9.8817(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.559(2)
_cell_angle_gamma                90
_cell_volume                     2828.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.10

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             1484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.097
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70326
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         28.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6960
_reflns_number_gt                5582
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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)+(0.0663P)²+5.3970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6960
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Br1 Br 0.96651(4) 0.24410(2) 0.59279(5) 0.05171(16) Uani 1 1 d . . . . .
Co1 Co 0.44023(3) 0.13140(2) 0.19775(4) 0.01154(11) Uani 1 1 d . . . . .
O1 O 0.3644(2) 0.27821(9) 0.0378(2) 0.0233(5) Uani 1 1 d . . . . .
O2 O 0.5096(2) 0.28636(8) 0.2977(2) 0.0210(5) Uani 1 1 d . . . . .
O3 O 0.5391(2) -0.02315(9) 0.1800(3) 0.0292(6) Uani 1 1 d . . . . .
O4 O 0.3470(3) -0.01306(10) 0.3233(3) 0.0401(7) Uani 1 1 d . . . . .
O5 O 0.8094(3) 0.19893(14) 0.3021(3) 0.0489(8) Uani 1 1 d . . . . .
H5B H 0.8475 0.2121 0.3889 0.073 Uiso 1 1 d R U . . .
H5C H 0.8573 0.2064 0.2290 0.073 Uiso 1 1 d R U . . .
O6 O 0.8114(3) 0.08527(15) 0.3292(4) 0.0528(8) Uani 1 1 d . . . . .
H6B H 0.8336 0.1210 0.3068 0.079 Uiso 1 1 d R U . . .
H6C H 0.8562 0.0736 0.4199 0.079 Uiso 1 1 d R U . . .
O7 O 0.9194(3) 0.13319(16) 0.7714(4) 0.0582(9) Uani 1 1 d . . . . .
H7B H 0.9308 0.1582 0.7010 0.087 Uiso 1 1 d R U . . .
H7C H 0.9896 0.1318 0.8445 0.087 Uiso 1 1 d R U . . .
O8 O 1.0591(9) 0.1419(3) 1.0152(11) 0.056(2) Uani 0.55 1 d . . P A 1
H8B H 1.0126 0.1531 1.0662 0.084 Uiso 0.55 1 d R U P A 1
H8C H 1.1164 0.1633 1.0209 0.084 Uiso 0.55 1 d R U P A 1
O8' O 1.0410(11) 0.1158(5) 1.0419(12) 0.062(3) Uani 0.45 1 d . . P B 2
H8D H 1.0336 0.1448 1.0860 0.093 Uiso 0.45 1 d R U P B 2
H8E H 1.1128 0.1093 1.0507 0.093 Uiso 0.45 1 d R U P B 2
O9 O 0.3984(3) 0.10674(14) 0.6050(3) 0.0483(8) Uani 1 1 d . . . . .
H9B H 0.4396 0.0764 0.6491 0.072 Uiso 1 1 d R U . . .
H9C H 0.4402 0.1414 0.6342 0.072 Uiso 1 1 d R U . . .
O10 O 0.0985(3) -0.04608(12) 0.4062(4) 0.0471(8) Uani 1 1 d . . . . .
H10B H 0.1422 -0.0139 0.3988 0.071 Uiso 1 1 d R U . . .
H10C H 0.1164 -0.0742 0.3393 0.071 Uiso 1 1 d R U . . .
O11 O -0.0700(10) 0.0029(4) 0.2246(14) 0.051(3) Uani 0.5 1 d . . P C 1
H11A H -0.0875 0.0406 0.2302 0.076 Uiso 0.5 1 d R U P C 1
H11B H -0.0561 -0.0138 0.3186 0.076 Uiso 0.5 1 d R U P C 1
O11' O -0.0496(11) 0.0202(4) 0.1878(13) 0.057(3) Uani 0.5 1 d . . P D 2
H11C H -0.1004 0.0288 0.2508 0.085 Uiso 0.5 1 d R U P D 2
H11D H -0.0271 0.0540 0.1423 0.085 Uiso 0.5 1 d R U P D 2
O12 O 0.0989(6) 0.0348(3) 0.0687(6) 0.0506(17) Uani 0.5 1 d . . P E 1
H12A H 0.0285 0.0244 0.0976 0.076 Uiso 0.5 1 d R U P E 1
H12B H 0.0993 0.0749 0.0509 0.076 Uiso 0.5 1 d R U P E 1
N1 N 0.4419(2) 0.20788(9) 0.1800(3) 0.0130(5) Uani 1 1 d . . . . .
N2 N 0.3417(2) 0.13533(10) 0.0208(3) 0.0141(5) Uani 1 1 d . . . . .
N3 N 0.2573(2) 0.19976(11) -0.1445(3) 0.0204(6) Uani 1 1 d . . . . .
N4 N 0.5416(2) 0.14639(10) 0.3704(3) 0.0142(5) Uani 1 1 d . . . . .
N5 N 0.6255(2) 0.22020(10) 0.5047(3) 0.0186(5) Uani 1 1 d . . . . .
N6 N 0.4389(2) 0.05492(10) 0.2203(3) 0.0162(5) Uani 1 1 d . . . . .
N7 N 0.5713(2) 0.11585(10) 0.1083(3) 0.0142(5) Uani 1 1 d . . . . .
N8 N 0.6759(2) 0.04149(11) 0.0399(3) 0.0221(6) Uani 1 1 d . . . . .
N9 N 0.3047(2) 0.12809(10) 0.2863(3) 0.0154(5) Uani 1 1 d . . . . .
N10 N 0.1919(3) 0.06442(12) 0.3846(3) 0.0251(6) Uani 1 1 d . . . . .
C1 C 0.3771(3) 0.23056(12) 0.0664(3) 0.0151(6) Uani 1 1 d . . . . .
C2 C 0.3204(3) 0.18646(12) -0.0267(3) 0.0156(6) Uani 1 1 d . . . . .
C3 C 0.2944(3) 0.09425(12) -0.0587(3) 0.0196(6) Uani 1 1 d . . . . .
H3A H 0.3065 0.0578 -0.0284 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2281(3) 0.10520(14) -0.1850(4) 0.0262(7) Uani 1 1 d . . . . .
H4A H 0.1950 0.0767 -0.2434 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2115(3) 0.15903(14) -0.2235(4) 0.0251(7) Uani 1 1 d . . . . .
H5A H 0.1657 0.1672 -0.3096 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5024(3) 0.23755(12) 0.2862(3) 0.0143(6) Uani 1 1 d . . . . .
C7 C 0.5611(3) 0.19947(12) 0.3953(3) 0.0152(6) Uani 1 1 d . . . . .
C8 C 0.5928(3) 0.11161(13) 0.4652(3) 0.0223(7) Uani 1 1 d . . . . .
H8A H 0.5816 0.0737 0.4514 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6617(3) 0.13003(14) 0.5828(4) 0.0248(7) Uani 1 1 d . . . . .
H9A H 0.6984 0.1055 0.6504 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6754(3) 0.18511(13) 0.5988(3) 0.0214(7) Uani 1 1 d . . . . .
H10A H 0.7219 0.1986 0.6795 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5219(3) 0.02522(12) 0.1723(3) 0.0175(6) Uani 1 1 d . . . . .
C12 C 0.5951(3) 0.06225(12) 0.1017(3) 0.0164(6) Uani 1 1 d . . . . .
C13 C 0.6357(3) 0.15064(13) 0.0507(3) 0.0184(6) Uani 1 1 d . . . . .
H13A H 0.6216 0.1885 0.0548 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7232(3) 0.13181(14) -0.0150(4) 0.0244(7) Uani 1 1 d . . . . .
H14A H 0.7704 0.1561 -0.0555 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7394(3) 0.07648(15) -0.0195(4) 0.0263(7) Uani 1 1 d . . . . .
H15A H 0.7975 0.0627 -0.0663 0.032 Uiso 1 1 calc R U . . .
C16 C 0.3583(3) 0.03343(13) 0.2901(3) 0.0210(7) Uani 1 1 d . . . . .
C17 C 0.2792(3) 0.07765(13) 0.3240(3) 0.0190(6) Uani 1 1 d . . . . .
C18 C 0.2349(3) 0.16850(13) 0.3108(3) 0.0183(6) Uani 1 1 d . . . . .
H18A H 0.2497 0.2045 0.2842 0.022 Uiso 1 1 calc R U . . .
C19 C 0.1410(3) 0.15790(15) 0.3748(4) 0.0262(7) Uani 1 1 d . . . . .
H19A H 0.0908 0.1861 0.3931 0.031 Uiso 1 1 calc R U . . .
C20 C 0.1233(3) 0.10523(16) 0.4106(4) 0.0284(8) Uani 1 1 d . . . . .
H20A H 0.0600 0.0973 0.4557 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 1.895(2) . ?
Co1 N6 1.899(2) . ?
Co1 N2 1.934(3) . ?
Co1 N7 1.940(3) . ?
Co1 N9 1.945(3) . ?
Co1 N4 1.948(3) . ?
O1 C1 1.212(4) . ?
O2 C6 1.211(4) . ?
O3 C11 1.210(4) . ?
O4 C16 1.206(4) . ?
N1 C1 1.368(4) . ?
N1 C6 1.377(4) . ?
N2 C3 1.345(4) . ?
N2 C2 1.354(4) . ?
N3 C2 1.314(4) . ?
N3 C5 1.330(4) . ?
N4 C8 1.338(4) . ?
N4 C7 1.345(4) . ?
N5 C7 1.316(4) . ?
N5 C10 1.333(4) . ?
N6 C11 1.367(4) . ?
N6 C16 1.369(4) . ?
N7 C13 1.333(4) . ?
N7 C12 1.355(4) . ?
N8 C12 1.316(4) . ?
N8 C15 1.339(5) . ?
N9 C18 1.338(4) . ?
N9 C17 1.346(4) . ?
N10 C17 1.314(4) . ?
N10 C20 1.341(5) . ?
C1 C2 1.507(4) . ?
C3 C4 1.384(5) . ?
C4 C5 1.386(5) . ?
C6 C7 1.508(4) . ?
C8 C9 1.379(5) . ?
C9 C10 1.374(5) . ?
C11 C12 1.504(4) . ?
C13 C14 1.385(5) . ?
C14 C15 1.379(5) . ?
C16 C17 1.508(5) . ?
C18 C19 1.386(5) . ?
C19 C20 1.371(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N6 178.62(11) . . ?
N1 Co1 N2 83.11(10) . . ?
N6 Co1 N2 98.07(11) . . ?
N1 Co1 N7 97.65(11) . . ?
N6 Co1 N7 83.09(11) . . ?
N2 Co1 N7 90.05(11) . . ?
N1 Co1 N9 96.06(11) . . ?
N6 Co1 N9 83.25(11) . . ?
N2 Co1 N9 89.72(11) . . ?
N7 Co1 N9 166.17(11) . . ?
N1 Co1 N4 82.99(10) . . ?
N6 Co1 N4 95.84(11) . . ?
N2 Co1 N4 166.08(10) . . ?
N7 Co1 N4 91.09(11) . . ?
N9 Co1 N4 92.45(11) . . ?
C1 N1 C6 123.8(2) . . ?
C1 N1 Co1 118.05(19) . . ?
C6 N1 Co1 118.05(19) . . ?
C3 N2 C2 117.7(3) . . ?
C3 N2 Co1 128.2(2) . . ?
C2 N2 Co1 114.1(2) . . ?
C2 N3 C5 116.5(3) . . ?
C8 N4 C7 116.9(3) . . ?
C8 N4 Co1 129.1(2) . . ?
C7 N4 Co1 114.0(2) . . ?
C7 N5 C10 116.6(3) . . ?
C11 N6 C16 124.2(3) . . ?
C11 N6 Co1 118.1(2) . . ?
C16 N6 Co1 117.6(2) . . ?
C13 N7 C12 118.1(3) . . ?
C13 N7 Co1 128.3(2) . . ?
C12 N7 Co1 113.6(2) . . ?
C12 N8 C15 116.8(3) . . ?
C18 N9 C17 117.8(3) . . ?
C18 N9 Co1 128.6(2) . . ?
C17 N9 Co1 113.6(2) . . ?
C17 N10 C20 116.2(3) . . ?
O1 C1 N1 128.2(3) . . ?
O1 C1 C2 122.2(3) . . ?
N1 C1 C2 109.6(2) . . ?
N3 C2 N2 125.7(3) . . ?
N3 C2 C1 119.2(3) . . ?
N2 C2 C1 115.0(3) . . ?
N2 C3 C4 119.8(3) . . ?
C3 C4 C5 117.8(3) . . ?
N3 C5 C4 122.5(3) . . ?
O2 C6 N1 128.2(3) . . ?
O2 C6 C7 122.4(3) . . ?
N1 C6 C7 109.4(2) . . ?
N5 C7 N4 125.9(3) . . ?
N5 C7 C6 118.6(3) . . ?
N4 C7 C6 115.5(3) . . ?
N4 C8 C9 120.9(3) . . ?
C10 C9 C8 117.6(3) . . ?
N5 C10 C9 122.1(3) . . ?
O3 C11 N6 128.9(3) . . ?
O3 C11 C12 121.7(3) . . ?
N6 C11 C12 109.5(2) . . ?
N8 C12 N7 124.9(3) . . ?
N8 C12 C11 119.5(3) . . ?
N7 C12 C11 115.5(3) . . ?
N7 C13 C14 120.3(3) . . ?
C15 C14 C13 117.7(3) . . ?
N8 C15 C14 122.2(3) . . ?
O4 C16 N6 128.5(3) . . ?
O4 C16 C17 121.8(3) . . ?
N6 C16 C17 109.7(3) . . ?
N10 C17 N9 125.6(3) . . ?
N10 C17 C16 118.7(3) . . ?
N9 C17 C16 115.6(3) . . ?
N9 C18 C19 120.1(3) . . ?
C20 C19 C18 117.6(3) . . ?
N10 C20 C19 122.6(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
N2 Co1 N1 C1 2.3(2) . . . . ?
N7 Co1 N1 C1 91.4(2) . . . . ?
N9 Co1 N1 C1 -86.7(2) . . . . ?
N4 Co1 N1 C1 -178.4(2) . . . . ?
N2 Co1 N1 C6 178.2(2) . . . . ?
N7 Co1 N1 C6 -92.7(2) . . . . ?
N9 Co1 N1 C6 89.2(2) . . . . ?
N4 Co1 N1 C6 -2.5(2) . . . . ?
N2 Co1 N6 C11 90.2(2) . . . . ?
N7 Co1 N6 C11 1.1(2) . . . . ?
N9 Co1 N6 C11 179.0(2) . . . . ?
N4 Co1 N6 C11 -89.2(2) . . . . ?
N2 Co1 N6 C16 -93.2(2) . . . . ?
N7 Co1 N6 C16 177.8(2) . . . . ?
N9 Co1 N6 C16 -4.4(2) . . . . ?
N4 Co1 N6 C16 87.4(2) . . . . ?
C6 N1 C1 O1 2.3(5) . . . . ?
Co1 N1 C1 O1 178.0(3) . . . . ?
C6 N1 C1 C2 -178.4(3) . . . . ?
Co1 N1 C1 C2 -2.7(3) . . . . ?
C5 N3 C2 N2 -0.5(5) . . . . ?
C5 N3 C2 C1 178.6(3) . . . . ?
C3 N2 C2 N3 0.0(5) . . . . ?
Co1 N2 C2 N3 179.2(3) . . . . ?
C3 N2 C2 C1 -179.2(3) . . . . ?
Co1 N2 C2 C1 0.0(3) . . . . ?
O1 C1 C2 N3 1.7(5) . . . . ?
N1 C1 C2 N3 -177.6(3) . . . . ?
O1 C1 C2 N2 -179.0(3) . . . . ?
N1 C1 C2 N2 1.7(4) . . . . ?
C2 N2 C3 C4 0.8(5) . . . . ?
Co1 N2 C3 C4 -178.3(3) . . . . ?
N2 C3 C4 C5 -1.0(5) . . . . ?
C2 N3 C5 C4 0.3(5) . . . . ?
C3 C4 C5 N3 0.5(6) . . . . ?
C1 N1 C6 O2 -0.5(5) . . . . ?
Co1 N1 C6 O2 -176.2(3) . . . . ?
C1 N1 C6 C7 178.5(3) . . . . ?
Co1 N1 C6 C7 2.8(3) . . . . ?
C10 N5 C7 N4 0.0(5) . . . . ?
C10 N5 C7 C6 179.7(3) . . . . ?
C8 N4 C7 N5 -0.4(5) . . . . ?
Co1 N4 C7 N5 179.5(3) . . . . ?
C8 N4 C7 C6 179.9(3) . . . . ?
Co1 N4 C7 C6 -0.3(3) . . . . ?
O2 C6 C7 N5 -2.2(5) . . . . ?
N1 C6 C7 N5 178.7(3) . . . . ?
O2 C6 C7 N4 177.5(3) . . . . ?
N1 C6 C7 N4 -1.6(4) . . . . ?
C7 N4 C8 C9 0.4(5) . . . . ?
Co1 N4 C8 C9 -179.5(3) . . . . ?
N4 C8 C9 C10 0.1(5) . . . . ?
C7 N5 C10 C9 0.5(5) . . . . ?
C8 C9 C10 N5 -0.6(5) . . . . ?
C16 N6 C11 O3 0.9(5) . . . . ?
Co1 N6 C11 O3 177.2(3) . . . . ?
C16 N6 C11 C12 -179.7(3) . . . . ?
Co1 N6 C11 C12 -3.3(3) . . . . ?
C15 N8 C12 N7 0.6(5) . . . . ?
C15 N8 C12 C11 -179.1(3) . . . . ?
C13 N7 C12 N8 -1.6(5) . . . . ?
Co1 N7 C12 N8 176.4(3) . . . . ?
C13 N7 C12 C11 178.1(3) . . . . ?
Co1 N7 C12 C11 -3.9(3) . . . . ?
O3 C11 C12 N8 3.9(5) . . . . ?
N6 C11 C12 N8 -175.6(3) . . . . ?
O3 C11 C12 N7 -175.8(3) . . . . ?
N6 C11 C12 N7 4.7(4) . . . . ?
C12 N7 C13 C14 0.8(4) . . . . ?
Co1 N7 C13 C14 -176.8(2) . . . . ?
N7 C13 C14 C15 0.7(5) . . . . ?
C12 N8 C15 C14 1.1(5) . . . . ?
C13 C14 C15 N8 -1.7(5) . . . . ?
C11 N6 C16 O4 1.5(6) . . . . ?
Co1 N6 C16 O4 -174.9(3) . . . . ?
C11 N6 C16 C17 -178.6(3) . . . . ?
Co1 N6 C16 C17 5.0(3) . . . . ?
C20 N10 C17 N9 -0.2(5) . . . . ?
C20 N10 C17 C16 -179.1(3) . . . . ?
C18 N9 C17 N10 -0.8(5) . . . . ?
Co1 N9 C17 N10 -179.5(3) . . . . ?
C18 N9 C17 C16 178.1(3) . . . . ?
Co1 N9 C17 C16 -0.5(3) . . . . ?
O4 C16 C17 N10 -3.8(5) . . . . ?
N6 C16 C17 N10 176.3(3) . . . . ?
O4 C16 C17 N9 177.1(3) . . . . ?
N6 C16 C17 N9 -2.8(4) . . . . ?
C17 N9 C18 C19 1.0(4) . . . . ?
Co1 N9 C18 C19 179.4(2) . . . . ?
N9 C18 C19 C20 -0.2(5) . . . . ?
C17 N10 C20 C19 1.0(5) . . . . ?
C18 C19 C20 N10 -0.8(5) . . . . ?

_refine_diff_density_max         1.716
_refine_diff_density_min         -1.549
_refine_diff_density_rms         0.102

