# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1532816'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2017-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H18 Cu2 N12 O8'
_chemical_formula_sum            'C24 H18 Cu2 N12 O8'
_chemical_formula_weight         729.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5524(15)
_cell_length_b                   10.2312(17)
_cell_length_c                   15.549(3)
_cell_angle_alpha                97.356(2)
_cell_angle_beta                 103.694(3)
_cell_angle_gamma                101.972(2)
_cell_volume                     1419.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.873
_cell_measurement_theta_min      2.666
_shelx_estimated_absorpt_T_max   0.776
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0605 before and 0.0422 after correction. The Ratio of minimum to maximum transmission is 0.8049. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7908
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3830
_reflns_number_total             5593
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (Bruker, 2016)'
_computing_data_collection       'SAINT V8.18C (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.18C (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+0.2162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 H1-O1
 0.82 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O8) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Riding coordinates:
 O2(H2A,H2B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.99432(6) 1.04143(5) 0.40412(4) 0.01984(17) Uani 1 1 d . U . . .
Cu2 Cu 0.67976(6) 0.84275(5) 0.35767(4) 0.02221(17) Uani 1 1 d . U . . .
O1 O 0.8814(3) 0.8851(3) 0.4347(2) 0.0206(5) Uani 1 1 d D U . . .
H1 H 0.920(5) 0.824(4) 0.420(3) 0.031 Uiso 1 1 d DR . . . .
O2 O 0.7568(4) 0.9531(4) 0.2509(2) 0.0360(7) Uani 1 1 d . U . . .
H2A H 0.7346 1.0375 0.2514 0.054 Uiso 1 1 d R . . . .
H2B H 0.8567 0.9675 0.2555 0.054 Uiso 1 1 d R . . . .
O3 O 0.6455(3) 1.0091(3) 0.4186(2) 0.0286(7) Uani 1 1 d . U . . .
O4 O 0.8658(3) 1.1593(3) 0.4427(2) 0.0222(6) Uani 1 1 d . U . . .
O5 O 0.6753(4) 0.6597(3) 0.3002(2) 0.0305(7) Uani 1 1 d . U . . .
O6 O 0.8748(4) 0.6021(4) 0.3787(2) 0.0341(8) Uani 1 1 d . U . . .
O7 O 1.1280(4) 0.9393(3) 0.3599(2) 0.0286(7) Uani 1 1 d . U . . .
O8 O 0.9943(5) 0.8992(6) 0.2165(3) 0.0673(15) Uani 1 1 d . U . . .
C1 C 0.7592(5) 1.3586(4) 0.5301(3) 0.0227(9) Uani 1 1 d . U . . .
H1A H 0.8584 1.3833 0.5300 0.027 Uiso 1 1 calc R . . . .
N2 N 0.7738(5) 1.5841(4) 0.6114(3) 0.0291(9) Uani 1 1 d . U . . .
N3 N 0.7561(7) 1.6474(5) 0.6883(4) 0.0654(19) Uani 1 1 d . U . . .
N4 N 0.8987(4) 1.7916(4) 0.6282(3) 0.0243(8) Uani 1 1 d . U . . .
N5 N 0.7103(6) 0.2067(5) 0.2313(4) 0.0606(16) Uani 1 1 d . U . . .
N6 N 0.3441(6) 0.2257(5) 0.1024(4) 0.0492(12) Uani 1 1 d . U . . .
N13 N 0.3068(8) 0.1205(7) 0.0320(5) 0.091(2) Uani 1 1 d . U . . .
N8 N 0.1142(6) 0.2104(7) 0.0324(4) 0.0656(15) Uani 1 1 d . U . . .
N9 N 1.4654(4) 0.8080(4) 0.2758(3) 0.0268(8) Uani 1 1 d . U . . .
N10 N 1.2651(5) 0.6349(5) 0.0465(3) 0.0429(11) Uani 1 1 d . U . . .
N11 N 1.3515(6) 0.5498(5) 0.0284(3) 0.0474(12) Uani 1 1 d . U . . .
N12 N 1.1602(7) 0.5305(7) -0.0924(4) 0.0731(19) Uani 1 1 d . U . . .
C7 C 0.7339(5) 1.1247(4) 0.4458(3) 0.0195(8) Uani 1 1 d . U . . .
C2 C 0.6718(5) 1.2320(4) 0.4886(3) 0.0210(8) Uani 1 1 d . U . . .
C3 C 0.6956(5) 1.4494(5) 0.5724(3) 0.0246(9) Uani 1 1 d . U . . .
C4 C 0.8355(8) 1.7728(6) 0.6963(5) 0.0575(19) Uani 1 1 d . U . . .
H4 H 0.8469 1.8418 0.7444 0.069 Uiso 1 1 calc R . . . .
C5 C 0.8579(5) 1.6719(4) 0.5768(3) 0.0238(9) Uani 1 1 d . U . . .
H5 H 0.8839 1.6508 0.5236 0.029 Uiso 1 1 calc R . . . .
C6 C 0.5476(5) 1.4071(5) 0.5735(3) 0.0272(10) Uani 1 1 d . U . . .
H6 H 0.5075 1.4672 0.6043 0.033 Uiso 1 1 calc R . . . .
N7 N 0.4609(4) 1.2848(4) 0.5325(3) 0.0298(9) Uani 1 1 d . U . . .
C8 C 0.5231(5) 1.2015(5) 0.4896(3) 0.0243(9) Uani 1 1 d . U . . .
H8 H 0.4632 1.1171 0.4583 0.029 Uiso 1 1 calc R . . . .
C9 C 0.7543(5) 0.5759(5) 0.3210(3) 0.0241(9) Uani 1 1 d . U . . .
C10 C 0.6860(6) 0.4328(5) 0.2687(3) 0.0275(9) Uani 1 1 d . U . . .
C11 C 0.7619(7) 0.3346(5) 0.2778(4) 0.0436(14) Uani 1 1 d . U . . .
H11 H 0.8555 0.3574 0.3188 0.052 Uiso 1 1 calc R . . . .
C12 C 0.5728(8) 0.1751(6) 0.1743(5) 0.0605(19) Uani 1 1 d . U . . .
H12 H 0.5339 0.0870 0.1415 0.073 Uiso 1 1 calc R . . . .
C13 C 0.4870(7) 0.2687(6) 0.1627(4) 0.0423(13) Uani 1 1 d . U . . .
C14 C 0.1693(9) 0.1154(9) -0.0065(6) 0.091(3) Uani 1 1 d . U . . .
H14 H 0.1131 0.0510 -0.0572 0.109 Uiso 1 1 calc R . . . .
C15 C 0.2274(7) 0.2801(7) 0.0994(4) 0.0482(13) Uani 1 1 d . U . . .
H15 H 0.2267 0.3562 0.1389 0.058 Uiso 1 1 calc R . . . .
C16 C 0.5454(6) 0.3991(5) 0.2102(4) 0.0326(11) Uani 1 1 d . U . . .
H16 H 0.4907 0.4642 0.2029 0.039 Uiso 1 1 calc R . . . .
C17 C 1.1025(6) 0.8929(5) 0.2775(4) 0.0327(11) Uani 1 1 d . U . . .
C18 C 1.2181(6) 0.8351(5) 0.2471(3) 0.0305(10) Uani 1 1 d . U . . .
C19 C 1.3595(5) 0.8557(5) 0.3023(3) 0.0248(9) Uani 1 1 d . U . . .
H19 H 1.3823 0.9049 0.3605 0.030 Uiso 1 1 calc R . . . .
C20 C 1.4346(6) 0.7413(5) 0.1929(3) 0.0283(10) Uani 1 1 d . U . . .
H20 H 1.5096 0.7115 0.1736 0.034 Uiso 1 1 calc R . . . .
C21 C 1.2945(6) 0.7135(6) 0.1331(4) 0.0333(11) Uani 1 1 d . U . . .
C22 C 1.2824(9) 0.4912(8) -0.0545(4) 0.0625(19) Uani 1 1 d . U . . .
H22 H 1.3158 0.4258 -0.0858 0.075 Uiso 1 1 calc R . . . .
C23 C 1.1539(8) 0.6205(9) -0.0280(4) 0.070(2) Uani 1 1 d . U . . .
H23 H 1.0812 0.6693 -0.0327 0.084 Uiso 1 1 calc R . . . .
C24 C 1.1850(6) 0.7634(6) 0.1607(4) 0.0376(13) Uani 1 1 d . U . . .
H24 H 1.0908 0.7488 0.1215 0.045 Uiso 1 1 calc R . . . .


_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
Cu1 Cu1 3.1863(12) 2_776 ?
Cu1 Cu2 3.1217(9) . ?
Cu1 O1 1.915(3) . ?
Cu1 O1 2.449(3) 2_776 ?
Cu1 H1 2.25(4) . ?
Cu1 H2B 2.3112 . ?
Cu1 O4 2.025(3) . ?
Cu1 O7 1.995(3) . ?
Cu1 N4 1.988(4) 2_786 ?
Cu2 O1 1.939(3) . ?
Cu2 H1 2.32(4) . ?
Cu2 O2 2.299(4) . ?
Cu2 O3 1.966(3) . ?
Cu2 O5 1.956(3) . ?
Cu2 N9 2.071(4) 1_455 ?
O1 Cu1 2.449(3) 2_776 ?
O1 H1 0.821(19) . ?
O2 H2A 0.9313 . ?
O2 H2B 0.9187 . ?
O3 C7 1.256(5) . ?
O4 C7 1.251(5) . ?
O5 C9 1.278(5) . ?
O6 C9 1.235(6) . ?
O7 C17 1.254(6) . ?
O8 C17 1.246(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.369(6) . ?
C1 C3 1.389(6) . ?
N2 N3 1.350(6) . ?
N2 C3 1.403(6) . ?
N2 C5 1.331(6) . ?
N3 C4 1.322(7) . ?
N4 Cu1 1.988(4) 2_786 ?
N4 C4 1.352(6) . ?
N4 C5 1.302(6) . ?
N5 C11 1.342(7) . ?
N5 C12 1.346(8) . ?
N6 N13 1.356(7) . ?
N6 C13 1.406(7) . ?
N6 C15 1.339(8) . ?
N13 C14 1.296(10) . ?
N8 C14 1.341(10) . ?
N8 C15 1.311(8) . ?
N9 Cu2 2.071(4) 1_655 ?
N9 C19 1.334(6) . ?
N9 C20 1.314(6) . ?
N10 N11 1.365(6) . ?
N10 C21 1.410(7) . ?
N10 C23 1.342(8) . ?
N11 C22 1.301(8) . ?
N12 C22 1.341(9) . ?
N12 C23 1.293(8) . ?
C7 C2 1.507(6) . ?
C2 C8 1.394(6) . ?
C3 C6 1.395(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 N7 1.331(6) . ?
N7 C8 1.333(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.510(7) . ?
C10 C11 1.359(7) . ?
C10 C16 1.378(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.386(8) . ?
C13 C16 1.371(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.497(6) . ?
C18 C19 1.375(7) . ?
C18 C24 1.377(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.386(7) . ?
C21 C24 1.384(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 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
Cu1 Cu1 H1 57.7(12) 2_776 . ?
Cu1 Cu1 H2B 139.3 2_776 . ?
Cu2 Cu1 Cu1 80.75(2) . 2_776 ?
Cu2 Cu1 H1 48.0(11) . . ?
Cu2 Cu1 H2B 60.2 . . ?
O1 Cu1 Cu1 50.12(10) . 2_776 ?
O1 Cu1 Cu1 36.89(7) 2_776 2_776 ?
O1 Cu1 Cu2 114.98(7) 2_776 . ?
O1 Cu1 Cu2 36.18(9) . . ?
O1 Cu1 O1 87.01(12) . 2_776 ?
O1 Cu1 H1 20.7(8) . . ?
O1 Cu1 H1 92.1(13) 2_776 . ?
O1 Cu1 H2B 174.7 2_776 . ?
O1 Cu1 H2B 89.3 . . ?
O1 Cu1 O4 91.72(13) . . ?
O1 Cu1 O7 93.58(13) . . ?
O1 Cu1 N4 176.65(14) . 2_786 ?
H1 Cu1 H2B 85.8 . . ?
O4 Cu1 Cu1 82.46(9) . 2_776 ?
O4 Cu1 Cu2 76.06(9) . . ?
O4 Cu1 O1 78.80(12) . 2_776 ?
O4 Cu1 H1 112.4(8) . . ?
O4 Cu1 H2B 97.6 . . ?
O7 Cu1 Cu1 102.14(10) . 2_776 ?
O7 Cu1 Cu2 107.52(10) . . ?
O7 Cu1 O1 102.99(13) . 2_776 ?
O7 Cu1 H1 72.9(8) . . ?
O7 Cu1 H2B 81.0 . . ?
O7 Cu1 O4 174.48(13) . . ?
N4 Cu1 Cu1 130.43(12) 2_786 2_776 ?
N4 Cu1 Cu2 141.24(12) 2_786 . ?
N4 Cu1 O1 93.62(14) 2_786 2_776 ?
N4 Cu1 H1 162.3(8) 2_786 . ?
N4 Cu1 H2B 89.9 2_786 . ?
N4 Cu1 O4 85.18(14) 2_786 . ?
N4 Cu1 O7 89.49(15) 2_786 . ?
Cu1 Cu2 H1 46.1(11) . . ?
O1 Cu2 Cu1 35.66(9) . . ?
O1 Cu2 H1 19.7(9) . . ?
O1 Cu2 O2 91.68(13) . . ?
O1 Cu2 O3 90.94(13) . . ?
O1 Cu2 O5 96.88(13) . . ?
O1 Cu2 N9 177.09(14) . 1_455 ?
O2 Cu2 Cu1 59.19(10) . . ?
O2 Cu2 H1 91.0(12) . . ?
O3 Cu2 Cu1 78.58(9) . . ?
O3 Cu2 H1 110.6(9) . . ?
O3 Cu2 O2 91.83(14) . . ?
O3 Cu2 N9 86.62(15) . 1_455 ?
O5 Cu2 Cu1 112.58(10) . . ?
O5 Cu2 H1 77.4(9) . . ?
O5 Cu2 O2 96.33(14) . . ?
O5 Cu2 O3 168.51(14) . . ?
O5 Cu2 N9 85.77(15) . 1_455 ?
N9 Cu2 Cu1 141.95(11) 1_455 . ?
N9 Cu2 H1 162.7(9) 1_455 . ?
N9 Cu2 O2 86.82(15) 1_455 . ?
Cu1 O1 Cu1 92.99(12) . 2_776 ?
Cu1 O1 Cu2 108.17(15) . . ?
Cu1 O1 H1 103(4) 2_776 . ?
Cu1 O1 H1 104(4) . . ?
Cu2 O1 Cu1 136.99(15) . 2_776 ?
Cu2 O1 H1 108(4) . . ?
Cu2 O2 H2A 112.6 . . ?
Cu2 O2 H2B 114.9 . . ?
H2A O2 H2B 106.6 . . ?
C7 O3 Cu2 128.2(3) . . ?
C7 O4 Cu1 128.8(3) . . ?
C9 O5 Cu2 133.3(3) . . ?
C17 O7 Cu1 120.6(3) . . ?
C2 C1 H1A 120.9 . . ?
C2 C1 C3 118.3(4) . . ?
C3 C1 H1A 120.9 . . ?
N3 N2 C3 121.5(4) . . ?
C5 N2 N3 110.1(4) . . ?
C5 N2 C3 128.0(4) . . ?
C4 N3 N2 102.2(4) . . ?
C4 N4 Cu1 131.9(3) . 2_786 ?
C5 N4 Cu1 124.0(3) . 2_786 ?
C5 N4 C4 103.6(4) . . ?
C11 N5 C12 116.8(5) . . ?
N13 N6 C13 122.5(5) . . ?
C15 N6 N13 108.7(5) . . ?
C15 N6 C13 128.8(5) . . ?
C14 N13 N6 103.2(6) . . ?
C15 N8 C14 103.3(6) . . ?
C19 N9 Cu2 122.9(3) . 1_655 ?
C20 N9 Cu2 118.3(3) . 1_655 ?
C20 N9 C19 118.7(4) . . ?
N11 N10 C21 121.3(5) . . ?
C23 N10 N11 108.1(5) . . ?
C23 N10 C21 130.6(5) . . ?
C22 N11 N10 101.9(5) . . ?
C23 N12 C22 102.2(6) . . ?
O3 C7 C2 115.0(4) . . ?
O4 C7 O3 127.8(4) . . ?
O4 C7 C2 117.2(4) . . ?
C1 C2 C7 121.7(4) . . ?
C1 C2 C8 118.4(4) . . ?
C8 C2 C7 119.9(4) . . ?
C1 C3 N2 122.1(4) . . ?
C1 C3 C6 119.1(4) . . ?
C6 C3 N2 118.7(4) . . ?
N3 C4 N4 113.9(5) . . ?
N3 C4 H4 123.0 . . ?
N4 C4 H4 123.0 . . ?
N2 C5 H5 124.9 . . ?
N4 C5 N2 110.2(4) . . ?
N4 C5 H5 124.9 . . ?
C3 C6 H6 118.4 . . ?
N7 C6 C3 123.2(4) . . ?
N7 C6 H6 118.4 . . ?
C6 N7 C8 116.4(4) . . ?
C2 C8 H8 117.8 . . ?
N7 C8 C2 124.5(5) . . ?
N7 C8 H8 117.8 . . ?
O5 C9 C10 113.9(4) . . ?
O6 C9 O5 126.2(4) . . ?
O6 C9 C10 119.9(4) . . ?
C11 C10 C9 120.8(5) . . ?
C11 C10 C16 118.5(5) . . ?
C16 C10 C9 120.6(4) . . ?
N5 C11 C10 124.0(5) . . ?
N5 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
N5 C12 H12 118.7 . . ?
N5 C12 C13 122.6(5) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 N6 118.5(5) . . ?
C16 C13 N6 122.9(5) . . ?
C16 C13 C12 118.6(5) . . ?
N13 C14 N8 114.8(7) . . ?
N13 C14 H14 122.6 . . ?
N8 C14 H14 122.6 . . ?
N6 C15 H15 125.0 . . ?
N8 C15 N6 110.0(6) . . ?
N8 C15 H15 125.0 . . ?
C10 C16 H16 120.3 . . ?
C13 C16 C10 119.3(5) . . ?
C13 C16 H16 120.3 . . ?
O7 C17 C18 117.9(5) . . ?
O8 C17 O7 126.2(5) . . ?
O8 C17 C18 115.7(5) . . ?
C19 C18 C17 121.8(5) . . ?
C19 C18 C24 118.5(4) . . ?
C24 C18 C17 119.6(5) . . ?
N9 C19 C18 122.8(5) . . ?
N9 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
N9 C20 H20 118.8 . . ?
N9 C20 C21 122.5(4) . . ?
C21 C20 H20 118.8 . . ?
C20 C21 N10 120.2(4) . . ?
C24 C21 N10 121.2(5) . . ?
C24 C21 C20 118.6(5) . . ?
N11 C22 N12 116.2(6) . . ?
N11 C22 H22 121.9 . . ?
N12 C22 H22 121.9 . . ?
N10 C23 H23 124.2 . . ?
N12 C23 N10 111.6(6) . . ?
N12 C23 H23 124.2 . . ?
C18 C24 C21 118.8(5) . . ?
C18 C24 H24 120.6 . . ?
C21 C24 H24 120.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A N5 0.93 1.85 2.764(6) 167.1 1_565

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
Cu1 O4 C7 O3 -6.3(8) . . . . ?
Cu1 O4 C7 C2 172.4(3) . . . . ?
Cu1 O7 C17 O8 -2.8(8) . . . . ?
Cu1 O7 C17 C18 171.3(3) . . . . ?
Cu1 N4 C4 N3 171.1(5) 2_786 . . . ?
Cu1 N4 C5 N2 -172.7(3) 2_786 . . . ?
Cu2 O3 C7 O4 -2.3(8) . . . . ?
Cu2 O3 C7 C2 178.9(3) . . . . ?
Cu2 O5 C9 O6 -13.5(8) . . . . ?
Cu2 O5 C9 C10 165.3(3) . . . . ?
Cu2 N9 C19 C18 178.5(4) 1_655 . . . ?
Cu2 N9 C20 C21 -179.8(4) 1_655 . . . ?
O3 C7 C2 C1 172.8(4) . . . . ?
O3 C7 C2 C8 -4.5(7) . . . . ?
O4 C7 C2 C1 -6.1(7) . . . . ?
O4 C7 C2 C8 176.6(4) . . . . ?
O5 C9 C10 C11 174.5(5) . . . . ?
O5 C9 C10 C16 -4.9(7) . . . . ?
O6 C9 C10 C11 -6.6(8) . . . . ?
O6 C9 C10 C16 173.9(5) . . . . ?
O7 C17 C18 C19 -13.0(8) . . . . ?
O7 C17 C18 C24 169.4(5) . . . . ?
O8 C17 C18 C19 161.7(5) . . . . ?
O8 C17 C18 C24 -15.9(8) . . . . ?
C1 C2 C8 N7 -3.6(8) . . . . ?
C1 C3 C6 N7 -2.9(8) . . . . ?
N2 N3 C4 N4 1.3(9) . . . . ?
N2 C3 C6 N7 174.8(5) . . . . ?
N3 N2 C3 C1 -143.3(6) . . . . ?
N3 N2 C3 C6 39.1(8) . . . . ?
N3 N2 C5 N4 0.6(6) . . . . ?
N5 C12 C13 N6 -179.3(7) . . . . ?
N5 C12 C13 C16 1.0(11) . . . . ?
N6 N13 C14 N8 0.9(12) . . . . ?
N6 C13 C16 C10 179.3(5) . . . . ?
N13 N6 C13 C12 -25.8(10) . . . . ?
N13 N6 C13 C16 153.9(7) . . . . ?
N13 N6 C15 N8 2.9(8) . . . . ?
N9 C20 C21 N10 -176.4(5) . . . . ?
N9 C20 C21 C24 3.0(8) . . . . ?
N10 N11 C22 N12 0.5(9) . . . . ?
N10 C21 C24 C18 177.5(5) . . . . ?
N11 N10 C21 C20 21.0(8) . . . . ?
N11 N10 C21 C24 -158.3(5) . . . . ?
N11 N10 C23 N12 1.3(9) . . . . ?
C7 C2 C8 N7 173.8(4) . . . . ?
C2 C1 C3 N2 -175.6(4) . . . . ?
C2 C1 C3 C6 2.0(7) . . . . ?
C3 C1 C2 C7 -176.4(4) . . . . ?
C3 C1 C2 C8 1.0(7) . . . . ?
C3 N2 N3 C4 -173.9(6) . . . . ?
C3 N2 C5 N4 172.9(5) . . . . ?
C3 C6 N7 C8 0.5(8) . . . . ?
C4 N4 C5 N2 0.2(6) . . . . ?
C5 N2 N3 C4 -1.1(7) . . . . ?
C5 N2 C3 C1 45.3(8) . . . . ?
C5 N2 C3 C6 -132.3(5) . . . . ?
C5 N4 C4 N3 -0.9(8) . . . . ?
C6 N7 C8 C2 2.8(8) . . . . ?
C9 C10 C11 N5 -177.6(6) . . . . ?
C9 C10 C16 C13 179.1(5) . . . . ?
C11 N5 C12 C13 0.4(11) . . . . ?
C11 C10 C16 C13 -0.4(8) . . . . ?
C12 N5 C11 C10 -1.8(11) . . . . ?
C12 C13 C16 C10 -1.0(9) . . . . ?
C13 N6 N13 C14 -179.2(7) . . . . ?
C13 N6 C15 N8 179.6(6) . . . . ?
C14 N8 C15 N6 -2.2(9) . . . . ?
C15 N6 N13 C14 -2.2(9) . . . . ?
C15 N6 C13 C12 157.9(7) . . . . ?
C15 N6 C13 C16 -22.4(10) . . . . ?
C15 N8 C14 N13 0.8(11) . . . . ?
C16 C10 C11 N5 1.8(10) . . . . ?
C17 C18 C19 N9 -178.3(5) . . . . ?
C17 C18 C24 C21 178.5(5) . . . . ?
C19 N9 C20 C21 -2.8(8) . . . . ?
C19 C18 C24 C21 0.8(8) . . . . ?
C20 N9 C19 C18 1.6(7) . . . . ?
C20 C21 C24 C18 -1.9(8) . . . . ?
C21 N10 N11 C22 175.8(6) . . . . ?
C21 N10 C23 N12 -175.1(7) . . . . ?
C22 N12 C23 N10 -0.9(10) . . . . ?
C23 N10 N11 C22 -1.0(7) . . . . ?
C23 N10 C21 C20 -163.0(7) . . . . ?
C23 N10 C21 C24 17.7(10) . . . . ?
C23 N12 C22 N11 0.3(10) . . . . ?
C24 C18 C19 N9 -0.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1532818'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-06-22 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         'C16 H14 Mn N8 O6'
_chemical_formula_sum            'C16 H14 Mn N8 O6'
_chemical_formula_weight         469.29

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'
Mn Mn 0.3368 0.7283 '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                   11.845(7)
_cell_length_b                   7.042(4)
_cell_length_c                   11.876(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.461(7)
_cell_angle_gamma                90
_cell_volume                     878.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2495
_cell_measurement_theta_min      3.435
_cell_measurement_theta_max      28.172

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             478
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.811
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   sadabs
_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  ω
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4457
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.938
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1714
_reflns_number_gt                1485
_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 APEX2'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  Diamond
_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)+(0.0800P)²+0.3000P] 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         1714
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Mn1 Mn 0.5000 1.0000 0.0000 0.0187(2) Uani 1 2 d S . P . .
O1 O 0.53322(14) 0.7126(2) 0.07511(15) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.61586(17) 0.4821(2) 0.21786(16) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.53971(16) 1.1010(2) 0.18731(14) 0.0308(4) Uani 1 1 d . . . . .
H3A H 0.5480 1.2168 0.1902 0.046 Uiso 1 1 d R U . . .
H3B H 0.4965 1.0906 0.2235 0.046 Uiso 1 1 d R U . . .
N1 N 0.83082(19) 0.6347(3) -0.02131(18) 0.0312(5) Uani 1 1 d . . . . .
N2 N 1.08631(16) 0.6066(3) 0.30674(16) 0.0215(4) Uani 1 1 d . . . . .
N3 N 1.10683(18) 0.6562(3) 0.42633(18) 0.0310(5) Uani 1 1 d . . . . .
N4 N 1.28986(17) 0.5689(3) 0.42796(18) 0.0253(4) Uani 1 1 d . . . . .
C1 C 0.61888(19) 0.5954(3) 0.13785(19) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.7373(2) 0.5956(3) 0.1196(2) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.7294(2) 0.6157(3) 0.0001(2) 0.0267(5) Uani 1 1 d . . . . .
H3 H 0.6490 0.6162 -0.0695 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9456(2) 0.6363(4) 0.0806(2) 0.0273(5) Uani 1 1 d . . . . .
H4 H 1.0172 0.6556 0.0690 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9615(2) 0.6102(3) 0.2027(2) 0.0224(5) Uani 1 1 d . . . . .
C6 C 0.8564(2) 0.5865(3) 0.2233(2) 0.0219(5) Uani 1 1 d . . . . .
H6 H 0.8658 0.5652 0.3044 0.026 Uiso 1 1 calc R U . . .
C7 C 1.1972(2) 0.5548(4) 0.3109(2) 0.0250(5) Uani 1 1 d . . . . .
H7 H 1.2072 0.5147 0.2414 0.030 Uiso 1 1 calc R U . . .
C8 C 1.2295(2) 0.6311(4) 0.4935(2) 0.0312(6) Uani 1 1 d . . . . .
H8 H 1.2721 0.6545 0.5803 0.037 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
Mn1 O3 2.1703(19) 3_675 ?
Mn1 O3 2.1703(19) . ?
Mn1 O1 2.1728(19) . ?
Mn1 O1 2.1729(19) 3_675 ?
Mn1 N4 2.280(2) 4_475 ?
Mn1 N4 2.280(2) 2_755 ?
O1 C1 1.253(3) . ?
O2 C1 1.254(3) . ?
O3 H3A 0.8200 . ?
O3 H3B 0.8095 . ?
N1 C4 1.340(3) . ?
N1 C3 1.345(3) . ?
N2 C7 1.342(3) . ?
N2 N3 1.371(3) . ?
N2 C5 1.424(3) . ?
N3 C8 1.307(3) . ?
N4 C7 1.319(3) . ?
N4 C8 1.350(3) . ?
N4 Mn1 2.280(2) 2_745 ?
C1 C2 1.515(3) . ?
C2 C6 1.382(3) . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 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
O3 Mn1 O3 180.0 3_675 . ?
O3 Mn1 O1 91.62(7) 3_675 . ?
O3 Mn1 O1 88.38(7) . . ?
O3 Mn1 O1 88.38(7) 3_675 3_675 ?
O3 Mn1 O1 91.62(7) . 3_675 ?
O1 Mn1 O1 180.0 . 3_675 ?
O3 Mn1 N4 82.10(7) 3_675 4_475 ?
O3 Mn1 N4 97.90(7) . 4_475 ?
O1 Mn1 N4 85.15(7) . 4_475 ?
O1 Mn1 N4 94.85(7) 3_675 4_475 ?
O3 Mn1 N4 97.90(7) 3_675 2_755 ?
O3 Mn1 N4 82.10(7) . 2_755 ?
O1 Mn1 N4 94.85(7) . 2_755 ?
O1 Mn1 N4 85.15(7) 3_675 2_755 ?
N4 Mn1 N4 180.0 4_475 2_755 ?
C1 O1 Mn1 143.29(14) . . ?
Mn1 O3 H3A 109.5 . . ?
Mn1 O3 H3B 128.6 . . ?
H3A O3 H3B 99.3 . . ?
C4 N1 C3 116.9(2) . . ?
C7 N2 N3 109.15(17) . . ?
C7 N2 C5 130.08(18) . . ?
N3 N2 C5 120.74(17) . . ?
C8 N3 N2 102.36(18) . . ?
C7 N4 C8 103.14(19) . . ?
C7 N4 Mn1 127.83(15) . 2_745 ?
C8 N4 Mn1 129.02(16) . 2_745 ?
O1 C1 O2 124.9(2) . . ?
O1 C1 C2 117.62(19) . . ?
O2 C1 C2 117.45(19) . . ?
C6 C2 C3 118.5(2) . . ?
C6 C2 C1 120.28(19) . . ?
C3 C2 C1 121.12(19) . . ?
N1 C3 C2 124.0(2) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C4 C5 122.3(2) . . ?
N1 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 N2 120.19(19) . . ?
C4 C5 N2 119.7(2) . . ?
C2 C6 C5 117.9(2) . . ?
C2 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N4 C7 N2 110.06(19) . . ?
N4 C7 H7 125.0 . . ?
N2 C7 H7 125.0 . . ?
N3 C8 N4 115.3(2) . . ?
N3 C8 H8 122.4 . . ?
N4 C8 H8 122.4 . . ?

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
C7 N2 N3 C8 0.3(3) . . . . ?
C5 N2 N3 C8 178.7(2) . . . . ?
Mn1 O1 C1 O2 141.2(2) . . . . ?
Mn1 O1 C1 C2 -36.3(3) . . . . ?
O1 C1 C2 C6 135.0(2) . . . . ?
O2 C1 C2 C6 -42.7(3) . . . . ?
O1 C1 C2 C3 -41.3(3) . . . . ?
O2 C1 C2 C3 141.1(2) . . . . ?
C4 N1 C3 C2 -0.9(4) . . . . ?
C6 C2 C3 N1 -2.8(4) . . . . ?
C1 C2 C3 N1 173.6(2) . . . . ?
C3 N1 C4 C5 3.2(4) . . . . ?
N1 C4 C5 C6 -1.8(4) . . . . ?
N1 C4 C5 N2 177.8(2) . . . . ?
C7 N2 C5 C6 151.5(2) . . . . ?
N3 N2 C5 C6 -26.5(3) . . . . ?
C7 N2 C5 C4 -28.1(3) . . . . ?
N3 N2 C5 C4 154.0(2) . . . . ?
C3 C2 C6 C5 4.0(3) . . . . ?
C1 C2 C6 C5 -172.34(19) . . . . ?
C4 C5 C6 C2 -1.9(3) . . . . ?
N2 C5 C6 C2 178.52(19) . . . . ?
C8 N4 C7 N2 0.1(3) . . . . ?
Mn1 N4 C7 N2 179.34(15) 2_745 . . . ?
N3 N2 C7 N4 -0.3(3) . . . . ?
C5 N2 C7 N4 -178.4(2) . . . . ?
N2 N3 C8 N4 -0.3(3) . . . . ?
C7 N4 C8 N3 0.1(3) . . . . ?
Mn1 N4 C8 N3 -179.09(18) 2_745 . . . ?

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.130

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1532821'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2017-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 Cu N4 O2.5, C H4 O, 2.5(H2 O)'
_chemical_formula_sum            'C9 H14 Cu N4 O6'
_chemical_formula_weight         337.78
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'-x, -x+y, -z+2/3'
'x-y, -y, -z+1/3'

_cell_length_a                   16.572(6)
_cell_length_b                   16.572(6)
_cell_length_c                   10.620(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2526(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    996
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.531
_cell_measurement_theta_min      2.386
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1276 before and 0.0759 after correction. The Ratio of minimum to maximum transmission is 0.7638. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1038
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1601
_diffrn_reflns_av_unetI/netI     0.1710
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15692
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         1.419
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2373
_reflns_number_total             4130
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (Bruker, 2016)'
_computing_data_collection       'SAINT V8.18C (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.18C (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
The structure contained large void, and the solvent and 
the positive or negative ions located in the void couldn't 
be identified because it was highly disordered had so small 
residual peak. Therefore, SQUEEZE in PLATON program was 
performed to remove the highly disordered solvent and ions. 
The numbers of masked ions and solvent molecules were 
confirmed by TG analysis. After calculation, the ions and 
solvent molecules were added in the _chemical_formula_moiety,
 _chemical_formula_sum and other relative items. 

;
_refine_ls_abs_structure_Flack   0.25(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.75(3)
 0.25(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N3A-N2 \\sim N2-N3
 with sigma of 0.02
 C8A-N4 \\sim N4-C8
 with sigma of 0.02
 C8-N3 \\sim C8A-N3A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N3A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N3)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 N2, N4, C7, N3, C8, N3A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(N3A)=Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(N3)=Sof(C8)=Sof(H8)=FVAR(1)
7.a Riding coordinates:
 C8(H8), C8A(H8A)
7.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.55544(6) 0.47365(6) 0.60712(7) 0.0299(2) Uani 1 1 d . . . . .
O1 O 0.4745(3) 0.3603(3) 0.4622(4) 0.0357(13) Uani 1 1 d . . . . .
C1 C 0.4755(5) 0.3818(5) 0.3494(6) 0.0262(17) Uani 1 1 d . . . . .
C2 C 0.4851(5) 0.3195(5) 0.2543(6) 0.0262(16) Uani 1 1 d . . . . .
C4 C 0.4924(5) 0.3386(5) 0.1244(5) 0.0274(16) Uani 1 1 d . . . . .
H4 H 0.4879 0.3889 0.0942 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5062(5) 0.2828(5) 0.0432(6) 0.0265(17) Uani 1 1 d . . . . .
C6 C 0.5103(5) 0.2078(5) 0.0883(6) 0.0316(19) Uani 1 1 d . . . . .
H6 H 0.5143 0.1673 0.0314 0.038 Uiso 1 1 calc R . . . .
N1 N 0.5088(5) 0.1908(4) 0.2116(5) 0.0338(16) Uani 1 1 d . . . . .
C3 C 0.4951(5) 0.2451(5) 0.2907(6) 0.0289(17) Uani 1 1 d . . . . .
H3 H 0.4921 0.2321 0.3763 0.035 Uiso 1 1 calc R . . . .
N2 N 0.5162(5) 0.3052(4) -0.0893(5) 0.0346(15) Uani 1 1 d D U . . .
N4 N 0.5386(4) 0.3745(5) -0.2690(5) 0.0354(17) Uani 1 1 d D U . A -1
C7 C 0.5277(6) 0.3801(6) -0.1459(6) 0.038(2) Uani 1 1 d . U . . .
H7 H 0.5282 0.4303 -0.1058 0.046 Uiso 1 1 calc R . . A .
O2 O 0.4709(4) 0.4482(3) 0.3042(4) 0.0368(14) Uani 1 1 d . . . B -1
O3 O 0.5734(4) 0.5734(4) 0.5000 0.0311(18) Uani 1 2 d S T P . .
N3 N 0.505(2) 0.2371(12) -0.1778(10) 0.040(5) Uani 0.62(5) 1 d D U . A 1
C8 C 0.517(2) 0.2819(13) -0.2805(14) 0.044(5) Uani 0.62(5) 1 d D U . A 1
H8 H 0.5110 0.2544 -0.3587 0.053 Uiso 0.62(5) 1 d R . . A 1
N3A N 0.549(3) 0.261(2) -0.172(2) 0.045(6) Uani 0.38(5) 1 d D U . A 2
C8A C 0.558(3) 0.304(2) -0.276(2) 0.035(7) Uani 0.38(5) 1 d D U . A 2
H8A H 0.5769 0.2884 -0.3498 0.042 Uiso 0.38(5) 1 d R . . 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
Cu1 O1 2.276(5) . ?
Cu1 N1 2.076(6) 3_665 ?
Cu1 N4 2.013(6) 1_556 ?
Cu1 O2 1.992(4) 4_556 ?
Cu1 O3 1.903(4) . ?
O1 C1 1.248(8) . ?
C1 C2 1.509(9) . ?
C1 O2 1.237(8) . ?
C2 C4 1.406(8) . ?
C2 C3 1.378(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(8) . ?
C5 C6 1.366(9) . ?
C5 N2 1.444(8) . ?
C6 H6 0.9300 . ?
C6 N1 1.337(8) . ?
N1 Cu1 2.076(6) 2_654 ?
N1 C3 1.332(8) . ?
C3 H3 0.9300 . ?
N2 C7 1.304(8) . ?
N2 N3 1.410(11) . ?
N2 N3A 1.409(17) . ?
N4 C7 1.330(8) . ?
N4 C8 1.394(15) . ?
N4 C8A 1.358(19) . ?
C7 H7 0.9300 . ?
O3 Cu1 1.903(4) 4_556 ?
N3 C8 1.280(13) . ?
C8 H8 0.9300 . ?
N3A C8A 1.278(19) . ?
C8A H8A 0.9299 . ?

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 Cu1 O1 92.1(2) 3_665 . ?
N4 Cu1 O1 89.1(2) 1_556 . ?
N4 Cu1 N1 92.3(2) 1_556 3_665 ?
O2 Cu1 O1 98.6(2) 4_556 . ?
O2 Cu1 N1 168.8(2) 4_556 3_665 ?
O2 Cu1 N4 85.1(2) 4_556 1_556 ?
O3 Cu1 O1 94.84(18) . . ?
O3 Cu1 N1 88.8(2) . 3_665 ?
O3 Cu1 N4 175.8(2) . 1_556 ?
O3 Cu1 O2 93.02(17) . 4_556 ?
C1 O1 Cu1 119.7(4) . . ?
O1 C1 C2 116.0(6) . . ?
O2 C1 O1 129.0(7) . . ?
O2 C1 C2 115.0(6) . . ?
C4 C2 C1 121.9(6) . . ?
C3 C2 C1 121.6(6) . . ?
C3 C2 C4 116.2(6) . . ?
C2 C4 H4 120.3 . . ?
C5 C4 C2 119.5(6) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 N2 118.6(6) . . ?
C6 C5 N2 121.6(6) . . ?
C5 C6 H6 119.0 . . ?
N1 C6 C5 122.0(6) . . ?
N1 C6 H6 119.0 . . ?
C6 N1 Cu1 119.9(5) . 2_654 ?
C3 N1 Cu1 122.2(4) . 2_654 ?
C3 N1 C6 117.9(6) . . ?
C2 C3 H3 117.8 . . ?
N1 C3 C2 124.4(6) . . ?
N1 C3 H3 117.8 . . ?
C7 N2 C5 129.6(6) . . ?
C7 N2 N3 110.8(7) . . ?
C7 N2 N3A 107.1(12) . . ?
N3 N2 C5 119.4(7) . . ?
N3A N2 C5 119.9(11) . . ?
C7 N4 C8 101.2(8) . . ?
C7 N4 C8A 102.2(12) . . ?
N2 C7 N4 110.3(6) . . ?
N2 C7 H7 124.9 . . ?
N4 C7 H7 124.9 . . ?
Cu1 O3 Cu1 118.4(4) . 4_556 ?
C8 N3 N2 100.4(12) . . ?
N4 C8 H8 121.7 . . ?
N3 C8 N4 116.5(13) . . ?
N3 C8 H8 121.8 . . ?
C8A N3A N2 102.8(19) . . ?
N3A C8A H8A 122.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 138.0(5) . . . . ?
Cu1 O1 C1 O2 -40.9(10) . . . . ?
Cu1 N1 C3 C2 178.5(6) 2_654 . . . ?
O1 C1 C2 C4 -176.4(7) . . . . ?
O1 C1 C2 C3 -2.0(11) . . . . ?
C1 C2 C4 C5 176.3(7) . . . . ?
C1 C2 C3 N1 -176.3(7) . . . . ?
C2 C4 C5 C6 1.7(12) . . . . ?
C2 C4 C5 N2 -178.3(7) . . . . ?
C4 C2 C3 N1 -1.6(11) . . . . ?
C4 C5 C6 N1 -5.5(12) . . . . ?
C4 C5 N2 C7 11.2(13) . . . . ?
C4 C5 N2 N3 -163.0(15) . . . . ?
C4 C5 N2 N3A 167(2) . . . . ?
C5 C6 N1 Cu1 -174.9(6) . . . 2_654 ?
C5 C6 N1 C3 5.6(12) . . . . ?
C5 N2 C7 N4 176.8(7) . . . . ?
C5 N2 N3 C8 178.4(11) . . . . ?
C5 N2 N3A C8A -173.5(15) . . . . ?
C6 C5 N2 C7 -168.8(8) . . . . ?
C6 C5 N2 N3 17.0(17) . . . . ?
C6 C5 N2 N3A -13(2) . . . . ?
C6 N1 C3 C2 -1.9(11) . . . . ?
C3 C2 C4 C5 1.6(11) . . . . ?
N2 C5 C6 N1 174.5(7) . . . . ?
N2 N3 C8 N4 3.2(17) . . . . ?
C7 N2 N3 C8 3.3(14) . . . . ?
C7 N2 N3A C8A -13(2) . . . . ?
C7 N4 C8 N3 -8.1(18) . . . . ?
O2 C1 C2 C4 2.7(11) . . . . ?
O2 C1 C2 C3 177.1(7) . . . . ?
N3 N2 C7 N4 -8.7(15) . . . . ?
C8 N4 C7 N2 9.6(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.75(3)
2 0.25(3)

####################################################################### 
# 
# 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 1532817'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-06-22 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         'C16 H14 Co N8 O6'
_chemical_formula_sum            'C16 H14 Co N8 O6'
_chemical_formula_weight         473.28

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'
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                   11.700(2)
_cell_length_b                   6.9671(12)
_cell_length_c                   11.849(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.789(3)
_cell_angle_gamma                90
_cell_volume                     854.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2876
_cell_measurement_theta_min      2.443
_cell_measurement_theta_max      28.373

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.066
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_process_details   sadabs
_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  ω
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4266
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.968
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1667
_reflns_number_gt                1488
_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 APEX2'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  Diamond
_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)+(0.0800P)²+0.3800P] 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         1667
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 1.0000 0.0000 0.01451(19) Uani 1 2 d S . P . .
O1 O 0.61385(18) 0.4826(2) 0.21645(17) 0.0220(4) Uani 1 1 d . . . . .
O2 O 0.53076(15) 0.7186(2) 0.07529(16) 0.0234(4) Uani 1 1 d . . . . .
O3 O 0.53421(17) 1.0993(2) 0.17865(15) 0.0250(4) Uani 1 1 d . . . . .
H3A H 0.4833 1.0486 0.1990 0.037 Uiso 1 1 d R U . . .
H3B H 0.5340 1.2072 0.2028 0.037 Uiso 1 1 d R U . . .
N1 N 0.83192(19) 0.6364(3) -0.02121(18) 0.0267(5) Uani 1 1 d . . . . .
N2 N 1.09246(18) 0.6074(3) 0.30887(17) 0.0180(4) Uani 1 1 d . . . . .
N3 N 1.11334(19) 0.6579(3) 0.42858(18) 0.0256(5) Uani 1 1 d . . . . .
N4 N 1.29897(18) 0.5679(3) 0.43049(18) 0.0189(4) Uani 1 1 d . . . . .
C1 C 0.6175(2) 0.5994(3) 0.13727(19) 0.0159(5) Uani 1 1 d . . . . .
C2 C 0.7374(2) 0.5983(3) 0.1194(2) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.7293(2) 0.6174(3) -0.0006(2) 0.0227(5) Uani 1 1 d . . . . .
H3 H 0.6477 0.6171 -0.0710 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8587(2) 0.5890(3) 0.2245(2) 0.0182(5) Uani 1 1 d . . . . .
H4 H 0.8683 0.5684 0.3060 0.022 Uiso 1 1 calc R U . . .
C5 C 0.9655(2) 0.6114(3) 0.2040(2) 0.0174(5) Uani 1 1 d . . . . .
C6 C 0.9485(2) 0.6391(3) 0.0812(2) 0.0224(5) Uani 1 1 d . . . . .
H6 H 1.0209 0.6603 0.0697 0.027 Uiso 1 1 calc R U . . .
C7 C 1.2039(2) 0.5537(4) 0.3127(2) 0.0198(5) Uani 1 1 d . . . . .
H7 H 1.2131 0.5125 0.2427 0.024 Uiso 1 1 calc R U . . .
C8 C 1.2378(2) 0.6321(4) 0.4965(2) 0.0251(5) Uani 1 1 d . . . . .
H8 H 1.2813 0.6559 0.5838 0.030 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 O3 2.0809(15) . ?
Co1 O3 2.0809(15) 3_675 ?
Co1 O2 2.1143(16) . ?
Co1 O2 2.1143(16) 3_675 ?
Co1 N4 2.1511(19) 4_475 ?
Co1 N4 2.1511(19) 2_755 ?
O1 C1 1.258(3) . ?
O2 C1 1.250(3) . ?
O3 H3A 0.8200 . ?
O3 H3B 0.8046 . ?
N1 C6 1.338(3) . ?
N1 C3 1.338(3) . ?
N2 C7 1.336(3) . ?
N2 N3 1.368(3) . ?
N2 C5 1.425(3) . ?
N3 C8 1.307(3) . ?
N4 C7 1.322(3) . ?
N4 C8 1.359(3) . ?
N4 Co1 2.1511(19) 2_745 ?
C1 C2 1.513(3) . ?
C2 C4 1.386(3) . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 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
O3 Co1 O3 180.0 . 3_675 ?
O3 Co1 O2 88.00(7) . . ?
O3 Co1 O2 92.00(7) 3_675 . ?
O3 Co1 O2 92.00(7) . 3_675 ?
O3 Co1 O2 88.00(7) 3_675 3_675 ?
O2 Co1 O2 180.0 . 3_675 ?
O3 Co1 N4 96.89(7) . 4_475 ?
O3 Co1 N4 83.11(7) 3_675 4_475 ?
O2 Co1 N4 84.17(7) . 4_475 ?
O2 Co1 N4 95.83(7) 3_675 4_475 ?
O3 Co1 N4 83.11(7) . 2_755 ?
O3 Co1 N4 96.89(7) 3_675 2_755 ?
O2 Co1 N4 95.83(7) . 2_755 ?
O2 Co1 N4 84.17(7) 3_675 2_755 ?
N4 Co1 N4 180.0 4_475 2_755 ?
C1 O2 Co1 142.71(15) . . ?
Co1 O3 H3A 109.5 . . ?
Co1 O3 H3B 129.9 . . ?
H3A O3 H3B 100.1 . . ?
C6 N1 C3 117.26(19) . . ?
C7 N2 N3 109.70(18) . . ?
C7 N2 C5 129.71(18) . . ?
N3 N2 C5 120.56(17) . . ?
C8 N3 N2 102.25(18) . . ?
C7 N4 C8 102.86(19) . . ?
C7 N4 Co1 128.28(16) . 2_745 ?
C8 N4 Co1 128.85(16) . 2_745 ?
O2 C1 O1 124.6(2) . . ?
O2 C1 C2 118.21(19) . . ?
O1 C1 C2 117.17(18) . . ?
C4 C2 C3 118.4(2) . . ?
C4 C2 C1 120.23(18) . . ?
C3 C2 C1 121.24(19) . . ?
N1 C3 C2 124.0(2) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
C2 C4 C5 117.81(19) . . ?
C2 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 N2 119.9(2) . . ?
C4 C5 N2 120.19(18) . . ?
N1 C6 C5 122.4(2) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N4 C7 N2 110.00(19) . . ?
N4 C7 H7 125.0 . . ?
N2 C7 H7 125.0 . . ?
N3 C8 N4 115.2(2) . . ?
N3 C8 H8 122.4 . . ?
N4 C8 H8 122.4 . . ?

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
C7 N2 N3 C8 0.5(3) . . . . ?
C5 N2 N3 C8 178.7(2) . . . . ?
Co1 O2 C1 O1 144.3(2) . . . . ?
Co1 O2 C1 C2 -33.8(3) . . . . ?
O2 C1 C2 C4 134.3(2) . . . . ?
O1 C1 C2 C4 -44.0(3) . . . . ?
O2 C1 C2 C3 -42.0(3) . . . . ?
O1 C1 C2 C3 139.7(2) . . . . ?
C6 N1 C3 C2 -0.8(4) . . . . ?
C4 C2 C3 N1 -3.2(4) . . . . ?
C1 C2 C3 N1 173.2(2) . . . . ?
C3 C2 C4 C5 3.9(3) . . . . ?
C1 C2 C4 C5 -172.48(18) . . . . ?
C2 C4 C5 C6 -0.9(3) . . . . ?
C2 C4 C5 N2 178.60(19) . . . . ?
C7 N2 C5 C6 -28.9(3) . . . . ?
N3 N2 C5 C6 153.3(2) . . . . ?
C7 N2 C5 C4 151.5(2) . . . . ?
N3 N2 C5 C4 -26.2(3) . . . . ?
C3 N1 C6 C5 4.1(4) . . . . ?
C4 C5 C6 N1 -3.2(3) . . . . ?
N2 C5 C6 N1 177.2(2) . . . . ?
C8 N4 C7 N2 0.3(3) . . . . ?
Co1 N4 C7 N2 179.15(15) 2_745 . . . ?
N3 N2 C7 N4 -0.5(3) . . . . ?
C5 N2 C7 N4 -178.4(2) . . . . ?
N2 N3 C8 N4 -0.4(3) . . . . ?
C7 N4 C8 N3 0.1(3) . . . . ?
Co1 N4 C8 N3 -178.81(16) 2_745 . . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1532820'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2017-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 Co2 N16 O9, 2(C4 H9 N O), 2(H2 O)'
_chemical_formula_sum            'C40 H44 Co2 N18 O13'
_chemical_formula_weight         1102.79
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_H-M_alt        'P 62'
_space_group_name_Hall           'P 62'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z'
'y, -x+y, z+2/3'
'x-y, x, z+1/3'

_cell_length_a                   16.140(2)
_cell_length_b                   16.140(2)
_cell_length_c                   16.758(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3780.6(12)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    6051
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.866
_cell_measurement_theta_min      2.524
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0777 before and 0.0613 after correction. The Ratio of minimum to maximum transmission is 0.8314. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23235
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         1.457
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4742
_reflns_number_total             5880
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (Bruker, 2016)'
_computing_data_collection       'SAINT V8.18C (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.18C (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
The structure contained large void, and the solvent and 
the positive or negative ions located in the void couldn't 
be identified because it was highly disordered had so small 
residual peak. Therefore, SQUEEZE in PLATON program was 
performed to remove the highly disordered solvent and ions. 
The numbers of masked ions and solvent molecules were 
confirmed by TG analysis. After calculation, the ions and 
solvent molecules were added in the _chemical_formula_moiety,
 _chemical_formula_sum and other relative items. 

;
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5880
_refine_ls_number_restraints     260
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0795P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.90(2)
 0.10(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
5.a Riding coordinates:
 O5(H5)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.62806(4) 0.04844(4) 0.14931(3) 0.03900(17) Uani 1 1 d . U . . .
O1 O 0.6720(2) -0.0273(2) 0.2218(2) 0.0521(8) Uani 1 1 d . U . . .
O2 O 0.5385(2) -0.1195(3) 0.2899(2) 0.0657(11) Uani 1 1 d . U . . .
O3 O 0.6349(3) 0.5611(3) 0.4152(2) 0.0636(10) Uani 1 1 d . U . A -1
O4 O 0.5410(2) 0.4017(3) 0.4172(2) 0.0557(8) Uani 1 1 d . U . . .
O5 O 0.5000 0.0000 0.2182(2) 0.0367(8) Uani 1 2 d S TU P . .
H5 H 0.4955 -0.0492 0.2433 0.055 Uiso 1 1 d R . . . .
N1 N 0.6628(3) -0.2498(3) 0.4093(2) 0.0449(8) Uani 1 1 d . U . B -1
N2 N 0.8998(3) -0.1381(4) 0.3186(3) 0.0673(12) Uani 1 1 d . U . . .
N3 N 0.9498(4) -0.1121(5) 0.2539(3) 0.0878(16) Uani 1 1 d . U . . .
N4 N 1.0322(4) -0.1233(7) 0.3448(5) 0.131(3) Uani 1 1 d . U . . .
N5 N 0.7087(3) 0.1665(3) 0.2257(3) 0.0518(8) Uani 1 1 d . U . . .
N6 N 0.8309(4) 0.2731(5) 0.2980(5) 0.108(2) Uani 1 1 d . U . . .
N7 N 0.7607(3) 0.2961(4) 0.2927(4) 0.0803(16) Uani 1 1 d . U . . .
N8 N 0.8734(4) 0.5386(5) 0.3730(7) 0.145(3) Uani 1 1 d . U . . .
C1 C 0.6234(3) -0.0915(3) 0.2706(3) 0.0421(9) Uani 1 1 d . U . . .
C2 C 0.6713(3) -0.1390(3) 0.3099(3) 0.0414(8) Uani 1 1 d . U . . .
C3 C 0.7647(3) -0.1133(3) 0.2932(3) 0.0473(10) Uani 1 1 d . U . . .
H3 H 0.7996 -0.0675 0.2547 0.057 Uiso 1 1 calc R . . . .
C4 C 0.6232(3) -0.2076(3) 0.3696(3) 0.0456(10) Uani 1 1 d . U . . .
H4 H 0.5605 -0.2242 0.3817 0.055 Uiso 1 1 calc R . . B .
C5 C 0.8052(3) -0.1584(4) 0.3359(3) 0.0567(13) Uani 1 1 d . U . . .
C6 C 0.7526(3) -0.2258(4) 0.3919(3) 0.0542(12) Uani 1 1 d . U . . .
H6 H 0.7805 -0.2560 0.4189 0.065 Uiso 1 1 calc R . . B .
C7 C 0.9561(5) -0.1434(7) 0.3790(5) 0.095(2) Uani 1 1 d . U . . .
H7 H 0.9404 -0.1585 0.4325 0.115 Uiso 1 1 calc R . . . .
C8 C 1.0338(5) -0.1081(6) 0.2660(6) 0.0925(19) Uani 1 1 d . U . . .
H8 H 1.0812 -0.0974 0.2291 0.111 Uiso 1 1 calc R . . . .
C9 C 0.7972(5) 0.1963(6) 0.2514(5) 0.085(2) Uani 1 1 d . U . . .
H9 H 0.8319 0.1664 0.2381 0.102 Uiso 1 1 calc R . . . .
C10 C 0.6908(4) 0.2328(4) 0.2472(3) 0.0587(12) Uani 1 1 d . U . . .
H10 H 0.6366 0.2356 0.2328 0.070 Uiso 1 1 calc R . . . .
C11 C 0.7700(4) 0.3782(5) 0.3303(5) 0.091(2) Uani 1 1 d . U . . .
C12 C 0.8596(5) 0.4555(6) 0.3423(7) 0.133(4) Uani 1 1 d . U . . .
H12 H 0.9127 0.4503 0.3287 0.159 Uiso 1 1 calc R . . . .
C13 C 0.6901(4) 0.3833(5) 0.3509(4) 0.0655(14) Uani 1 1 d . U . . .
H13 H 0.6289 0.3313 0.3435 0.079 Uiso 1 1 calc R . . . .
C14 C 0.7036(4) 0.4676(5) 0.3827(4) 0.0740(17) Uani 1 1 d . U . . .
C15 C 0.7949(5) 0.5430(6) 0.3911(7) 0.119(3) Uani 1 1 d . U . . .
H15 H 0.8027 0.6005 0.4105 0.143 Uiso 1 1 calc R . . . .
C16 C 0.6195(4) 0.4794(4) 0.4070(3) 0.0569(11) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.083(3) . ?
Co1 O4 2.071(3) 2_654 ?
Co1 O5 2.144(2) . ?
Co1 N1 2.134(4) 5_664 ?
Co1 N5 2.118(4) . ?
O1 C1 1.243(5) . ?
O2 C1 1.253(5) . ?
O3 Co1 2.052(4) 6 ?
O3 C16 1.220(6) . ?
O4 Co1 2.071(3) 3_665 ?
O4 C16 1.272(6) . ?
O5 Co1 2.144(2) 4_655 ?
O5 H5 0.8699 . ?
N1 C4 1.324(6) . ?
N1 C6 1.332(6) . ?
N2 N3 1.289(7) . ?
N2 C5 1.423(6) . ?
N2 C7 1.392(8) . ?
N3 C8 1.340(9) . ?
N4 C7 1.242(9) . ?
N4 C8 1.341(12) . ?
N5 C9 1.331(7) . ?
N5 C10 1.291(7) . ?
N6 N7 1.360(7) . ?
N6 C9 1.330(9) . ?
N7 C10 1.322(7) . ?
N7 C11 1.405(8) . ?
N8 C12 1.348(10) . ?
N8 C15 1.340(9) . ?
C1 C2 1.488(6) . ?
C2 C3 1.378(6) . ?
C2 C4 1.404(6) . ?
C3 H3 0.9300 . ?
C3 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.373(9) . ?
C11 C13 1.377(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.374(8) . ?
C14 C15 1.370(9) . ?
C14 C16 1.517(8) . ?
C15 H15 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
O1 Co1 O5 91.22(11) . . ?
O1 Co1 N1 88.45(13) . 5_664 ?
O1 Co1 N5 86.54(16) . . ?
O4 Co1 O1 172.69(15) 2_654 . ?
O4 Co1 O5 91.17(11) 2_654 . ?
O4 Co1 N1 89.65(14) 2_654 5_664 ?
O4 Co1 N5 86.44(17) 2_654 . ?
N1 Co1 O5 175.89(13) 5_664 . ?
N5 Co1 O5 92.84(13) . . ?
N5 Co1 N1 91.23(16) . 5_664 ?
C1 O1 Co1 127.9(3) . . ?
C16 O3 Co1 136.3(3) . 6 ?
C16 O4 Co1 131.0(3) . 3_665 ?
Co1 O5 Co1 114.91(18) . 4_655 ?
Co1 O5 H5 107.6 4_655 . ?
Co1 O5 H5 102.7 . . ?
C4 N1 C6 118.4(4) . . ?
N3 N2 C5 132.1(5) . . ?
N3 N2 C7 108.1(5) . . ?
C7 N2 C5 119.7(5) . . ?
N2 N3 C8 110.0(6) . . ?
C7 N4 C8 115.4(7) . . ?
C9 N5 Co1 125.9(4) . . ?
C10 N5 Co1 128.5(4) . . ?
C10 N5 C9 104.8(5) . . ?
C9 N6 N7 102.0(5) . . ?
N6 N7 C11 121.2(5) . . ?
C10 N7 N6 109.4(5) . . ?
C10 N7 C11 129.3(5) . . ?
C15 N8 C12 116.7(6) . . ?
O1 C1 O2 126.3(4) . . ?
O1 C1 C2 116.5(4) . . ?
O2 C1 C2 117.1(4) . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 C4 118.2(4) . . ?
C4 C2 C1 119.8(4) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C5 117.8(4) . . ?
C5 C3 H3 121.1 . . ?
N1 C4 C2 123.0(4) . . ?
N1 C4 H4 118.5 . . ?
C2 C4 H4 118.5 . . ?
C3 C5 N2 120.3(4) . . ?
C6 C5 N2 119.4(4) . . ?
C6 C5 C3 120.2(4) . . ?
N1 C6 C5 122.3(4) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N2 C7 H7 128.1 . . ?
N4 C7 N2 103.7(7) . . ?
N4 C7 H7 128.1 . . ?
N3 C8 N4 102.3(6) . . ?
N3 C8 H8 128.9 . . ?
N4 C8 H8 128.9 . . ?
N5 C9 H9 123.5 . . ?
N6 C9 N5 113.1(5) . . ?
N6 C9 H9 123.5 . . ?
N5 C10 N7 110.1(5) . . ?
N5 C10 H10 125.0 . . ?
N7 C10 H10 125.0 . . ?
C12 C11 N7 119.3(6) . . ?
C12 C11 C13 120.1(6) . . ?
C13 C11 N7 120.5(5) . . ?
N8 C12 C11 122.3(7) . . ?
N8 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C11 C13 H13 121.1 . . ?
C14 C13 C11 117.9(5) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 C16 121.3(5) . . ?
C15 C14 C13 119.2(6) . . ?
C15 C14 C16 119.5(6) . . ?
N8 C15 C14 123.7(7) . . ?
N8 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
O3 C16 O4 128.0(5) . . ?
O3 C16 C14 116.9(5) . . ?
O4 C16 C14 115.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 O2 -5.0(8) . . . . ?
Co1 O1 C1 C2 175.3(3) . . . . ?
Co1 O3 C16 O4 28.3(11) 6 . . . ?
Co1 O3 C16 C14 -151.0(5) 6 . . . ?
Co1 O4 C16 O3 -21.8(10) 3_665 . . . ?
Co1 O4 C16 C14 157.5(4) 3_665 . . . ?
Co1 N5 C9 N6 179.2(6) . . . . ?
Co1 N5 C10 N7 -177.3(4) . . . . ?
O1 C1 C2 C3 0.0(7) . . . . ?
O1 C1 C2 C4 175.7(5) . . . . ?
O2 C1 C2 C3 -179.7(5) . . . . ?
O2 C1 C2 C4 -4.0(7) . . . . ?
N2 N3 C8 N4 -6.6(10) . . . . ?
N2 C5 C6 N1 -178.2(5) . . . . ?
N3 N2 C5 C3 -29.0(10) . . . . ?
N3 N2 C5 C6 147.8(7) . . . . ?
N3 N2 C7 N4 -1.9(10) . . . . ?
N6 N7 C10 N5 3.4(9) . . . . ?
N6 N7 C11 C12 28.2(14) . . . . ?
N6 N7 C11 C13 -155.4(8) . . . . ?
N7 N6 C9 N5 -6.5(10) . . . . ?
N7 C11 C12 N8 175.5(10) . . . . ?
N7 C11 C13 C14 -175.9(7) . . . . ?
C1 C2 C3 C5 176.8(5) . . . . ?
C1 C2 C4 N1 -177.1(5) . . . . ?
C2 C3 C5 N2 177.0(5) . . . . ?
C2 C3 C5 C6 0.3(8) . . . . ?
C3 C2 C4 N1 -1.2(8) . . . . ?
C3 C5 C6 N1 -1.4(9) . . . . ?
C4 N1 C6 C5 1.2(8) . . . . ?
C4 C2 C3 C5 1.0(7) . . . . ?
C5 N2 N3 C8 -175.8(6) . . . . ?
C5 N2 C7 N4 179.2(7) . . . . ?
C6 N1 C4 C2 0.1(7) . . . . ?
C7 N2 N3 C8 5.6(9) . . . . ?
C7 N2 C5 C3 149.5(7) . . . . ?
C7 N2 C5 C6 -33.7(9) . . . . ?
C7 N4 C8 N3 5.7(13) . . . . ?
C8 N4 C7 N2 -2.5(13) . . . . ?
C9 N5 C10 N7 -7.1(7) . . . . ?
C9 N6 N7 C10 1.9(10) . . . . ?
C9 N6 N7 C11 -176.3(7) . . . . ?
C10 N5 C9 N6 8.7(9) . . . . ?
C10 N7 C11 C12 -149.6(10) . . . . ?
C10 N7 C11 C13 26.9(13) . . . . ?
C11 N7 C10 N5 -178.6(7) . . . . ?
C11 C13 C14 C15 1.3(12) . . . . ?
C11 C13 C14 C16 180.0(7) . . . . ?
C12 N8 C15 C14 2(2) . . . . ?
C12 C11 C13 C14 0.5(13) . . . . ?
C13 C11 C12 N8 -1.0(17) . . . . ?
C13 C14 C15 N8 -2.9(17) . . . . ?
C13 C14 C16 O3 -161.7(6) . . . . ?
C13 C14 C16 O4 18.9(10) . . . . ?
C15 N8 C12 C11 -0.5(19) . . . . ?
C15 C14 C16 O3 17.0(11) . . . . ?
C15 C14 C16 O4 -162.4(8) . . . . ?
C16 C14 C15 N8 178.4(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90(2)
2 0.10(2)

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1532819'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2017-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C9.5 H9.5 Co1 N5 O4.5, Cl0.5, C3 H7 N1 O1, 2(H2 O)'
_chemical_formula_sum            'C12.50 H20.50 Cl0.50 Co N6 O7.50'
_chemical_formula_weight         451.50
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'-x, -x+y, -z+1/3'
'x-y, -y, -z+2/3'

_cell_length_a                   17.377(10)
_cell_length_b                   17.377(10)
_cell_length_c                   10.730(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2806(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    3758
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.285
_cell_measurement_theta_min      2.331
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0991 before and 0.0860 after correction. The Ratio of minimum to maximum transmission is 0.8259. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1398
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15040
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.353
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3300
_reflns_number_total             3845
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (Bruker, 2016)'
_computing_data_collection       'SAINT V8.18C (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.18C (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.281
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1569
_refine_special_details          
;
 Refined as a 2-component inversion twin.
The structure contained large void, and the solvent and 
the positive or negative ions located in the void couldn't 
be identified because it was highly disordered had so small 
residual peak. Therefore, SQUEEZE in PLATON program was 
performed to remove the highly disordered solvent and ions. 
The numbers of masked ions and solvent molecules were 
confirmed by TG analysis. After calculation, the ions and 
solvent molecules were added in the _chemical_formula_moiety,
 _chemical_formula_sum and other relative items. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.93(4)
 0.07(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Restrained distances
 C1-N2
 1.3 with sigma of 0.02
 N2-C3
 1.3 with sigma of 0.02
 N2-C2
 1.3 with sigma of 0.02
 C1-O3
 1.2 with sigma of 0.02
4. Rigid bond restraints
 N1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1, N1, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O3, N2, C1, C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N4, C11A, N5, C10A, N7, C11, N7A, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N7A) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(Cl1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
6. Others
 Sof(C11)=Sof(H11)=Sof(N7A)=Sof(C10)=Sof(H10)=1-FVAR(1)
 Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(N7)=FVAR(1)
 Fixed Sof: H3A(0.5) H3B(0.5) N2(0.5) C1(0.5) H1(0.5) C2(0.5) H2A(0.5)
 H2B(0.5) H2C(0.5) C3(0.5) H3C(0.5) H3D(0.5) H3E(0.5)
7.a Riding coordinates:
 O3(H3A,H3B), C2(H2A,H2B,H2C), C3(H3C,H3D,H3E)
7.b Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C8(H8), C6(H6), C4(H4), C10A(H10A), C1(H1), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co -0.57557(6) -0.08604(5) -0.05213(7) 0.0229(3) Uani 1 1 d . . . . .
O4 O -0.8808(3) -0.3937(3) 0.1398(4) 0.0308(11) Uani 1 1 d . . . . .
O3 O -0.6525(5) -0.0750(5) 0.0999(6) 0.0617(17) Uani 1 1 d D U . . .
H3A H -0.6098 -0.0303 0.1365 0.093 Uiso 0.5 1 d R . . A 2
H3B H -0.6975 -0.0683 0.0914 0.093 Uiso 0.5 1 d R . . A 2
O5 O -0.9769(3) -0.4624(4) -0.0174(5) 0.0458(15) Uani 1 1 d . . . . .
O1 O -0.5996(5) 0.0000 -0.1667 0.0353(14) Uani 1 2 d S TU P . .
N3 N -0.6992(4) -0.2010(4) -0.1106(5) 0.0340(14) Uani 1 1 d . . . . .
N4 N -0.7956(4) -0.3158(4) -0.4090(5) 0.0408(15) Uani 1 1 d . U . . .
N1 N -0.6758(8) 0.0000 -0.1667 0.074(3) Uani 1 2 d S TU P . .
C11A C -0.7506(13) -0.3197(15) -0.5927(15) 0.066(7) Uani 0.63(3) 1 d . U . B 1
H11A H -0.7168 -0.3020 -0.6675 0.079 Uiso 0.63(3) 1 calc R . . B 1
N5 N -0.8361(4) -0.3830(4) -0.5899(5) 0.0350(13) Uani 1 1 d . U . . .
C7 C -0.8388(5) -0.3363(4) -0.0669(5) 0.0266(13) Uani 1 1 d . . . . .
C8 C -0.7620(5) -0.2602(5) -0.0282(6) 0.0288(15) Uani 1 1 d . . . . .
H8 H -0.7524 -0.2484 0.0586 0.035 Uiso 1 1 calc R . . . .
C6 C -0.8531(5) -0.3563(4) -0.1940(6) 0.0318(15) Uani 1 1 d . . . . .
H6 H -0.9042 -0.4086 -0.2228 0.038 Uiso 1 1 calc R . . . .
C4 C -0.7156(5) -0.2201(5) -0.2338(6) 0.0330(16) Uani 1 1 d . . . . .
H4 H -0.6747 -0.1795 -0.2928 0.040 Uiso 1 1 calc R . . . .
C10A C -0.8600(16) -0.3766(16) -0.4784(19) 0.039(6) Uani 0.63(3) 1 d . U . B 1
H10A H -0.9190 -0.4127 -0.4487 0.047 Uiso 0.63(3) 1 calc R . . B 1
C5 C -0.7896(5) -0.2964(5) -0.2768(6) 0.0314(16) Uani 1 1 d . . . . .
C9 C -0.9048(5) -0.4031(5) 0.0276(6) 0.0275(15) Uani 1 1 d . . . . .
N7 N -0.7162(10) -0.2829(15) -0.4820(12) 0.077(9) Uani 0.63(3) 1 d . U . B 1
N2 N -0.7360(15) -0.0299(16) 0.208(2) 0.097(5) Uani 0.5 1 d D U . C -1
C1 C -0.6672(16) -0.0191(16) 0.141(2) 0.077(5) Uani 0.5 1 d D U . C -1
H1 H -0.6239 0.0407 0.1222 0.093 Uiso 0.5 1 calc R . . C -1
Cl1 Cl -1.0000 -0.3225(16) -0.3333 0.330(10) Uani 1 2 d S TU P . .
C2 C -0.742(3) 0.034(2) 0.267(3) 0.133(9) Uani 0.5 1 d D U . C -1
H2A H -0.6866 0.0889 0.2611 0.199 Uiso 0.5 1 d R . . C -1
H2B H -0.7593 0.0217 0.3529 0.199 Uiso 0.5 1 d R . . C -1
H2C H -0.7870 0.0398 0.2220 0.199 Uiso 0.5 1 d R . . C -1
C3 C -0.793(2) -0.112(2) 0.241(3) 0.118(7) Uani 0.5 1 d D U . C -1
H3C H -0.8191 -0.1406 0.1634 0.177 Uiso 0.5 1 d R . . C -1
H3D H -0.8367 -0.1106 0.2930 0.177 Uiso 0.5 1 d R . . C -1
H3E H -0.7696 -0.1458 0.2826 0.177 Uiso 0.5 1 d R . . C -1
O2 O -0.6918(10) 0.0508(11) -0.2120(15) 0.153(5) Uani 1 1 d . U . . .
C11 C -0.7833(19) -0.2979(19) -0.600(2) 0.041(5) Uani 0.37(3) 1 d . U . B 2
H11 H -0.7653 -0.2715 -0.6805 0.049 Uiso 0.37(3) 1 calc R . . B 2
N7A N -0.7532(19) -0.2454(14) -0.4936(18) 0.050(6) Uani 0.37(3) 1 d . U . B 2
C10 C -0.853(3) -0.396(3) -0.463(4) 0.027(5) Uani 0.37(3) 1 d . U . B 2
H10 H -0.8945 -0.4496 -0.4217 0.033 Uiso 0.37(3) 1 calc R . . B 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 O4 2.110(5) 3_444 ?
Co1 O3 2.178(6) . ?
Co1 O5 2.072(5) 4_565 ?
Co1 O1 2.132(5) . ?
Co1 N3 2.170(6) . ?
Co1 N5 2.159(6) 3_445 ?
O4 Co1 2.110(5) 2_455 ?
O4 C9 1.257(8) . ?
O3 H3A 0.8555 . ?
O3 H3B 0.8495 . ?
O3 C1 1.203(18) . ?
O5 Co1 2.072(5) 4_455 ?
O5 C9 1.254(9) . ?
O1 Co1 2.132(5) 6_554 ?
O1 N1 1.324(15) . ?
N3 C8 1.381(9) . ?
N3 C4 1.357(8) . ?
N4 C10A 1.32(2) . ?
N4 C5 1.449(8) . ?
N4 N7 1.434(16) . ?
N4 N7A 1.40(2) . ?
N4 C10 1.37(5) . ?
N1 O2 1.157(13) . ?
N1 O2 1.157(13) 6_554 ?
C11A H11A 0.9500 . ?
C11A N5 1.337(18) . ?
C11A N7 1.340(18) . ?
N5 Co1 2.159(6) 2_454 ?
N5 C10A 1.29(2) . ?
N5 C11 1.30(3) . ?
N5 C10 1.39(4) . ?
C7 C8 1.392(9) . ?
C7 C6 1.399(9) . ?
C7 C9 1.537(9) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.394(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(9) . ?
C10A H10A 0.9500 . ?
N2 C1 1.33(2) . ?
N2 C2 1.33(2) . ?
N2 C3 1.32(2) . ?
C1 H1 0.9500 . ?
C2 H2A 0.9597 . ?
C2 H2B 0.9592 . ?
C2 H2C 0.9597 . ?
C3 H3C 0.9600 . ?
C3 H3D 0.9609 . ?
C3 H3E 0.9598 . ?
O2 O2 1.81(3) 6_554 ?
C11 H11 0.9500 . ?
C11 N7A 1.39(3) . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 O3 170.7(2) 3_444 . ?
O4 Co1 O1 94.93(19) 3_444 . ?
O4 Co1 N3 87.1(2) 3_444 . ?
O4 Co1 N5 88.7(2) 3_444 3_445 ?
O5 Co1 O4 97.2(2) 4_565 3_444 ?
O5 Co1 O3 89.6(3) 4_565 . ?
O5 Co1 O1 89.70(18) 4_565 . ?
O5 Co1 N3 175.4(2) 4_565 . ?
O5 Co1 N5 86.1(2) 4_565 3_445 ?
O1 Co1 O3 91.5(3) . . ?
O1 Co1 N3 91.6(2) . . ?
O1 Co1 N5 174.78(17) . 3_445 ?
N3 Co1 O3 85.9(3) . . ?
N5 Co1 O3 85.4(3) 3_445 . ?
N5 Co1 N3 92.3(2) 3_445 . ?
C9 O4 Co1 130.0(4) . 2_455 ?
Co1 O3 H3A 97.5 . . ?
Co1 O3 H3B 125.3 . . ?
H3A O3 H3B 111.4 . . ?
C1 O3 Co1 137.0(13) . . ?
C9 O5 Co1 134.8(4) . 4_455 ?
Co1 O1 Co1 113.7(4) 6_554 . ?
N1 O1 Co1 123.13(18) . 6_554 ?
N1 O1 Co1 123.13(18) . . ?
C8 N3 Co1 123.4(4) . . ?
C4 N3 Co1 119.7(4) . . ?
C4 N3 C8 116.8(6) . . ?
C10A N4 C5 132.2(11) . . ?
C10A N4 N7 105.8(12) . . ?
N7 N4 C5 119.9(7) . . ?
N7A N4 C5 119.0(10) . . ?
C10 N4 C5 125.3(18) . . ?
C10 N4 N7A 114.6(18) . . ?
O2 N1 O1 128.5(9) 6_554 . ?
O2 N1 O1 128.5(9) . . ?
O2 N1 O2 103.1(18) . 6_554 ?
N5 C11A H11A 122.6 . . ?
N5 C11A N7 114.9(13) . . ?
N7 C11A H11A 122.6 . . ?
C11A N5 Co1 130.8(9) . 2_454 ?
C10A N5 Co1 125.3(11) . 2_454 ?
C10A N5 C11A 102.9(13) . . ?
C11 N5 Co1 134.8(11) . 2_454 ?
C11 N5 C10 104(2) . . ?
C10 N5 Co1 119.8(19) . 2_454 ?
C8 C7 C6 119.6(6) . . ?
C8 C7 C9 121.3(6) . . ?
C6 C7 C9 118.9(6) . . ?
N3 C8 C7 122.8(6) . . ?
N3 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C7 C6 H6 121.3 . . ?
C5 C6 C7 117.4(6) . . ?
C5 C6 H6 121.3 . . ?
N3 C4 H4 118.7 . . ?
N3 C4 C5 122.6(6) . . ?
C5 C4 H4 118.7 . . ?
N4 C10A H10A 122.8 . . ?
N5 C10A N4 114.4(18) . . ?
N5 C10A H10A 122.8 . . ?
C6 C5 N4 120.8(6) . . ?
C4 C5 N4 118.3(5) . . ?
C4 C5 C6 120.8(6) . . ?
O4 C9 C7 117.3(6) . . ?
O5 C9 O4 127.3(6) . . ?
O5 C9 C7 115.3(5) . . ?
C11A N7 N4 100.6(11) . . ?
C1 N2 C2 126(3) . . ?
C3 N2 C1 115(2) . . ?
C3 N2 C2 117(3) . . ?
O3 C1 N2 129(2) . . ?
O3 C1 H1 115.7 . . ?
N2 C1 H1 115.7 . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 114.0 . . ?
N2 C2 H2C 104.7 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3C 103.1 . . ?
N2 C3 H3D 106.9 . . ?
N2 C3 H3E 118.1 . . ?
H3C C3 H3D 109.4 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N1 O2 O2 38.5(9) . 6_554 ?
N5 C11 H11 120.2 . . ?
N5 C11 N7A 119.7(19) . . ?
N7A C11 H11 120.2 . . ?
C11 N7A N4 95.7(17) . . ?
N4 C10 N5 105(3) . . ?
N4 C10 H10 127.6 . . ?
N5 C10 H10 127.6 . . ?

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
Co1 O4 C9 O5 30.0(11) 2_455 . . . ?
Co1 O4 C9 C7 -148.8(5) 2_455 . . . ?
Co1 O3 C1 N2 156(2) . . . . ?
Co1 O5 C9 O4 -5.5(13) 4_455 . . . ?
Co1 O5 C9 C7 173.3(6) 4_455 . . . ?
Co1 O1 N1 O2 -11.1(11) . . . 6_554 ?
Co1 O1 N1 O2 168.9(11) 6_554 . . 6_554 ?
Co1 O1 N1 O2 -11.1(11) 6_554 . . . ?
Co1 O1 N1 O2 168.9(11) . . . . ?
Co1 N3 C8 C7 -176.4(6) . . . . ?
Co1 N3 C4 C5 174.5(6) . . . . ?
Co1 N5 C10A N4 167.7(11) 2_454 . . . ?
Co1 N5 C11 N7A 170.4(17) 2_454 . . . ?
Co1 N5 C10 N4 -177.3(13) 2_454 . . . ?
O1 N1 O2 O2 180.001(2) . . . 6_554 ?
N3 C4 C5 N4 -172.8(7) . . . . ?
N3 C4 C5 C6 2.3(13) . . . . ?
C11A N5 C10A N4 -2(2) . . . . ?
N5 C11A N7 N4 -13(2) . . . . ?
N5 C11 N7A N4 2(3) . . . . ?
C7 C6 C5 N4 174.7(7) . . . . ?
C7 C6 C5 C4 -0.2(12) . . . . ?
C8 N3 C4 C5 -2.2(12) . . . . ?
C8 C7 C6 C5 -1.7(11) . . . . ?
C8 C7 C9 O4 -10.4(11) . . . . ?
C8 C7 C9 O5 170.7(7) . . . . ?
C6 C7 C8 N3 1.8(12) . . . . ?
C6 C7 C9 O4 164.7(7) . . . . ?
C6 C7 C9 O5 -14.2(10) . . . . ?
C4 N3 C8 C7 0.2(11) . . . . ?
C10A N4 C5 C6 13(2) . . . . ?
C10A N4 C5 C4 -172.2(17) . . . . ?
C10A N4 N7 C11A 11(2) . . . . ?
C5 N4 C10A N5 -169.1(11) . . . . ?
C5 N4 N7 C11A 176.3(14) . . . . ?
C5 N4 N7A C11 -176.6(15) . . . . ?
C5 N4 C10 N5 178.8(12) . . . . ?
C9 C7 C8 N3 176.8(7) . . . . ?
C9 C7 C6 C5 -176.9(7) . . . . ?
N7 N4 C10A N5 -6(2) . . . . ?
N7 N4 C5 C6 -148.6(15) . . . . ?
N7 N4 C5 C4 26.5(18) . . . . ?
N7 C11A N5 Co1 -158.9(15) . . . 2_454 ?
N7 C11A N5 C10A 10(2) . . . . ?
C2 N2 C1 O3 169(3) . . . . ?
C3 N2 C1 O3 5(5) . . . . ?
C11 N5 C10 N4 -8(3) . . . . ?
N7A N4 C5 C6 157.0(19) . . . . ?
N7A N4 C5 C4 -28(2) . . . . ?
N7A N4 C10 N5 11(3) . . . . ?
C10 N4 C5 C6 -10(2) . . . . ?
C10 N4 C5 C4 165(2) . . . . ?
C10 N4 N7A C11 -8(3) . . . . ?
C10 N5 C11 N7A 4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.93(4)
2 0.07(4)

