# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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 1552724'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O6 Zn'
_chemical_formula_weight         356.64

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'
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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2330(8)
_cell_length_b                   9.7370(8)
_cell_length_c                   10.4837(10)
_cell_angle_alpha                107.355(3)
_cell_angle_beta                 101.071(4)
_cell_angle_gamma                111.799(3)
_cell_volume                     699.98(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5179
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.784
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7549
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2458
_reflns_number_gt                2214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.7160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2458
_refine_ls_number_parameters     211
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_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
Zn1 Zn -0.20232(4) -0.14720(3) 0.00381(3) 0.02075(11) Uani 1 1 d . . . . .
O1 O -0.0575(2) 0.09143(19) 0.08808(19) 0.0230(4) Uani 1 1 d . . . . .
O2 O -0.3031(3) 0.1196(2) -0.0042(2) 0.0365(5) Uani 1 1 d . . . . .
O3 O -0.4011(3) -0.1634(3) 0.1030(2) 0.0351(5) Uani 1 1 d . . . . .
H3A H -0.486(5) -0.144(4) 0.070(4) 0.053 Uiso 1 1 d . U . . .
H3C H -0.358(5) -0.107(5) 0.186(4) 0.053 Uiso 1 1 d . U . . .
O4 O 0.0397(3) 0.8901(2) 0.2941(2) 0.0332(5) Uani 1 1 d . . . . .
O5 O -0.1201(2) 0.7128(2) 0.06947(18) 0.0240(4) Uani 1 1 d . . . . .
O6 O 0.1995(7) 0.0132(9) 0.6084(4) 0.162(3) Uani 1 1 d D . . . .
H6B H 0.095(8) -0.049(11) 0.613(10) 0.243 Uiso 1 1 d D U . . .
H6A H 0.177(14) 0.011(12) 0.525(5) 0.243 Uiso 1 1 d D U . . .
N1 N 0.6154(3) 0.7381(2) 0.7992(2) 0.0197(4) Uani 1 1 d . . . . .
C1 C -0.1450(3) 0.1765(3) 0.0790(3) 0.0196(5) Uani 1 1 d . . . . .
C2 C -0.0401(3) 0.3523(3) 0.1769(3) 0.0176(5) Uani 1 1 d . . . . .
C3 C 0.0968(3) 0.4027(3) 0.3050(3) 0.0199(5) Uani 1 1 d . . . . .
H3 H 0.1213 0.3265 0.3299 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1980(3) 0.5662(3) 0.3969(2) 0.0199(5) Uani 1 1 d . . . . .
C5 C 0.1575(4) 0.6773(3) 0.3566(3) 0.0227(5) Uani 1 1 d . . . . .
H5 H 0.2241 0.7867 0.4164 0.027 Uiso 1 1 calc R U . . .
C6 C 0.0197(3) 0.6282(3) 0.2292(3) 0.0187(5) Uani 1 1 d . . . . .
C7 C -0.0794(3) 0.4652(3) 0.1394(3) 0.0183(5) Uani 1 1 d . . . . .
H7 H -0.1721 0.4313 0.0542 0.022 Uiso 1 1 calc R U . . .
C8 C -0.0218(3) 0.7546(3) 0.1966(3) 0.0193(5) Uani 1 1 d . . . . .
C9 C 0.3456(4) 0.6233(3) 0.5341(3) 0.0212(5) Uani 1 1 d . . . . .
C10 C 0.4932(4) 0.7795(3) 0.5962(3) 0.0296(6) Uani 1 1 d . . . . .
H10 H 0.5046 0.8480 0.5490 0.036 Uiso 1 1 calc R U . . .
C11 C 0.6213(4) 0.8317(3) 0.7265(3) 0.0277(6) Uani 1 1 d . . . . .
H11 H 0.7171 0.9370 0.7669 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4808(3) 0.5835(3) 0.7376(3) 0.0194(5) Uani 1 1 d . . . . .
C13 C 0.3443(3) 0.5259(3) 0.6067(3) 0.0220(5) Uani 1 1 d . . . . .
H13 H 0.2506 0.4198 0.5674 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4830(4) 0.4759(3) 0.8128(3) 0.0319(7) Uani 1 1 d . . . . .
H14A H 0.3802 0.3701 0.7576 0.048 Uiso 1 1 calc R U . . .
H14B H 0.5975 0.4685 0.8252 0.048 Uiso 1 1 calc R U . . .
H14C H 0.4726 0.5199 0.9042 0.048 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
Zn1 O5 1.9641(16) 1_545 ?
Zn1 O1 1.9784(16) . ?
Zn1 N1 2.047(2) 1_444 ?
Zn1 O3 2.084(2) . ?
Zn1 O1 2.4575(18) 2 ?
O1 C1 1.295(3) . ?
O1 Zn1 2.4575(18) 2 ?
O2 C1 1.226(3) . ?
O3 H3A 0.83(4) . ?
O3 H3C 0.80(4) . ?
O4 C8 1.242(3) . ?
O5 C8 1.270(3) . ?
O5 Zn1 1.9641(16) 1_565 ?
O6 H6B 0.87(2) . ?
O6 H6A 0.85(2) . ?
N1 C11 1.344(3) . ?
N1 C12 1.348(3) . ?
N1 Zn1 2.047(2) 1_666 ?
C1 C2 1.498(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.393(3) . ?
C3 C4 1.396(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(3) . ?
C4 C9 1.485(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(3) . ?
C6 C8 1.506(3) . ?
C7 H7 0.9300 . ?
C9 C13 1.380(3) . ?
C9 C10 1.395(4) . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.393(3) . ?
C12 C14 1.490(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Zn1 O1 123.12(7) 1_545 . ?
O5 Zn1 N1 113.69(8) 1_545 1_444 ?
O1 Zn1 N1 118.98(8) . 1_444 ?
O5 Zn1 O3 96.02(8) 1_545 . ?
O1 Zn1 O3 97.77(8) . . ?
N1 Zn1 O3 96.65(9) 1_444 . ?
O5 Zn1 O1 86.08(7) 1_545 2 ?
O1 Zn1 O1 75.01(7) . 2 ?
N1 Zn1 O1 89.20(7) 1_444 2 ?
O3 Zn1 O1 172.35(8) . 2 ?
C1 O1 Zn1 118.64(15) . . ?
C1 O1 Zn1 115.15(15) . 2 ?
Zn1 O1 Zn1 104.99(7) . 2 ?
Zn1 O3 H3A 117(3) . . ?
Zn1 O3 H3C 114(3) . . ?
H3A O3 H3C 106(4) . . ?
C8 O5 Zn1 124.00(15) . 1_565 ?
H6B O6 H6A 107(3) . . ?
C11 N1 C12 118.1(2) . . ?
C11 N1 Zn1 115.89(16) . 1_666 ?
C12 N1 Zn1 125.67(16) . 1_666 ?
O2 C1 O1 123.2(2) . . ?
O2 C1 C2 121.0(2) . . ?
O1 C1 C2 115.8(2) . . ?
C3 C2 C7 120.0(2) . . ?
C3 C2 C1 119.9(2) . . ?
C7 C2 C1 120.1(2) . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C9 119.9(2) . . ?
C3 C4 C9 121.9(2) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 C8 122.2(2) . . ?
C5 C6 C8 118.3(2) . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O4 C8 O5 124.8(2) . . ?
O4 C8 C6 118.6(2) . . ?
O5 C8 C6 116.6(2) . . ?
C13 C9 C10 116.7(2) . . ?
C13 C9 C4 122.2(2) . . ?
C10 C9 C4 121.2(2) . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.2(2) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N1 C12 C13 120.8(2) . . ?
N1 C12 C14 118.2(2) . . ?
C13 C12 C14 121.0(2) . . ?
C9 C13 C12 121.3(2) . . ?
C9 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 -16.6(3) . . . . ?
Zn1 O1 C1 O2 109.0(3) 2 . . . ?
Zn1 O1 C1 C2 163.85(16) . . . . ?
Zn1 O1 C1 C2 -70.6(2) 2 . . . ?
O2 C1 C2 C3 153.3(3) . . . . ?
O1 C1 C2 C3 -27.2(3) . . . . ?
O2 C1 C2 C7 -26.9(4) . . . . ?
O1 C1 C2 C7 152.7(2) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 179.1(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C9 -179.8(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C9 C4 C5 C6 -179.7(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C4 C5 C6 C8 177.2(2) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C8 C6 C7 C2 -177.7(2) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
C1 C2 C7 C6 -179.1(2) . . . . ?
Zn1 O5 C8 O4 -2.4(4) 1_565 . . . ?
Zn1 O5 C8 C6 176.90(16) 1_565 . . . ?
C7 C6 C8 O4 163.3(2) . . . . ?
C5 C6 C8 O4 -14.2(4) . . . . ?
C7 C6 C8 O5 -16.0(4) . . . . ?
C5 C6 C8 O5 166.5(2) . . . . ?
C5 C4 C9 C13 153.4(3) . . . . ?
C3 C4 C9 C13 -26.7(4) . . . . ?
C5 C4 C9 C10 -26.7(4) . . . . ?
C3 C4 C9 C10 153.3(3) . . . . ?
C13 C9 C10 C11 -3.7(4) . . . . ?
C4 C9 C10 C11 176.3(3) . . . . ?
C12 N1 C11 C10 2.7(4) . . . . ?
Zn1 N1 C11 C10 -171.0(2) 1_666 . . . ?
C9 C10 C11 N1 1.4(5) . . . . ?
C11 N1 C12 C13 -4.3(4) . . . . ?
Zn1 N1 C12 C13 168.79(18) 1_666 . . . ?
C11 N1 C12 C14 175.2(3) . . . . ?
Zn1 N1 C12 C14 -11.7(3) 1_666 . . . ?
C10 C9 C13 C12 2.1(4) . . . . ?
C4 C9 C13 C12 -177.9(2) . . . . ?
N1 C12 C13 C9 1.9(4) . . . . ?
C14 C12 C13 C9 -177.6(3) . . . . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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 1552725'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cl2 Mn3 N2 O11'
_chemical_formula_weight         800.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   18.019(3)
_cell_length_b                   7.6710(12)
_cell_length_c                   23.088(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3191.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             1612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.398
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60718
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.868
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2805
_reflns_number_gt                2382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+5.5255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2805
_refine_ls_number_parameters     224
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.55034(2) 0.80547(6) 0.40066(2) 0.01726(14) Uani 1 1 d . . . . .
Mn2 Mn 0.5000 0.5000 0.5000 0.01697(16) Uani 1 2 d S . P . .
Cl1 Cl 0.54775(5) 0.47590(11) 0.39423(3) 0.0297(2) Uani 1 1 d . . . . .
N1 N 0.60402(14) 0.6555(4) 0.81540(10) 0.0224(6) Uani 1 1 d . . . . .
O1 O 0.56368(10) 0.7443(3) 0.50295(9) 0.0210(5) Uani 1 1 d . . . . .
O2 O 0.65940(11) 0.7936(3) 0.44611(8) 0.0304(6) Uani 1 1 d D . . . .
O3 O 0.90980(11) 0.8483(3) 0.52909(9) 0.0289(5) Uani 1 1 d . . . . .
O4 O 0.93441(11) 0.6943(3) 0.60902(9) 0.0309(6) Uani 1 1 d . . . . .
O5 O 0.54351(18) 1.0735(4) 0.42877(12) 0.0497(7) Uani 1 1 d D . . . .
H5C H 0.541(3) 0.992(4) 0.4051(15) 0.075 Uiso 1 1 d D U . . .
H5D H 0.576(2) 1.147(4) 0.4187(18) 0.075 Uiso 1 1 d D U . . .
O6 O 0.6850(7) 0.221(2) 0.3888(5) 0.076(3) Uani 0.307(9) 1 d . U P A 1
O6' O 0.7912(11) 0.622(4) 0.4002(8) 0.076(3) Uani 0.193(9) 1 d D U P A 2
C1 C 0.63359(16) 0.7633(4) 0.49557(12) 0.0199(6) Uani 1 1 d . . . . .
C2 C 0.89088(16) 0.7643(4) 0.57344(12) 0.0199(7) Uani 1 1 d . . . . .
C3 C 0.68456(16) 0.7481(4) 0.54599(12) 0.0177(6) Uani 1 1 d . . . . .
C4 C 0.76063(16) 0.7676(4) 0.53796(12) 0.0192(7) Uani 1 1 d . . . . .
H4 H 0.7791 0.7956 0.5015 0.023 Uiso 1 1 calc R U . . .
C5 C 0.80907(15) 0.7455(4) 0.58413(12) 0.0173(6) Uani 1 1 d . . . . .
C6 C 0.78107(16) 0.7097(4) 0.63893(12) 0.0185(6) Uani 1 1 d . . . . .
H6 H 0.8135 0.6939 0.6698 0.022 Uiso 1 1 calc R U . . .
C7 C 0.70450(16) 0.6973(4) 0.64805(12) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.65691(16) 0.7146(4) 0.60098(12) 0.0197(7) Uani 1 1 d . . . . .
H8 H 0.6060 0.7035 0.6064 0.024 Uiso 1 1 calc R U . . .
C9 C 0.57701(17) 0.5639(4) 0.77025(12) 0.0217(7) Uani 1 1 d . . . . .
C10 C 0.61023(16) 0.5727(4) 0.71592(12) 0.0210(7) Uani 1 1 d . . . . .
H10 H 0.5901 0.5095 0.6853 0.025 Uiso 1 1 calc R U . . .
C11 C 0.67280(16) 0.6740(4) 0.70673(12) 0.0186(7) Uani 1 1 d . . . . .
C12 C 0.70214(18) 0.7613(5) 0.75417(13) 0.0315(8) Uani 1 1 d . . . . .
H12 H 0.7454 0.8267 0.7506 0.038 Uiso 1 1 calc R U . . .
C13 C 0.66581(18) 0.7493(5) 0.80687(13) 0.0335(9) Uani 1 1 d . . . . .
H13 H 0.6855 0.8098 0.8382 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5086(2) 0.4574(6) 0.77972(15) 0.0459(11) Uani 1 1 d . . . . .
H14A H 0.4954 0.3992 0.7444 0.069 Uiso 1 1 calc R U . . .
H14B H 0.5178 0.3724 0.8094 0.069 Uiso 1 1 calc R U . . .
H14C H 0.4686 0.5322 0.7915 0.069 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 O4 2.101(2) 3_466 ?
Mn1 O5 2.159(3) . ?
Mn1 N1 2.214(2) 8_575 ?
Mn1 O2 2.230(2) . ?
Mn1 O1 2.420(2) . ?
Mn1 Cl1 2.5329(10) . ?
Mn1 H5C 1.44(3) . ?
Mn2 O3 2.109(2) 7_755 ?
Mn2 O3 2.109(2) 3_466 ?
Mn2 O1 2.199(2) 5_666 ?
Mn2 O1 2.199(2) . ?
Mn2 Cl1 2.5958(8) 5_666 ?
Mn2 Cl1 2.5959(8) . ?
N1 C13 1.340(4) . ?
N1 C9 1.348(4) . ?
N1 Mn1 2.214(2) 8_576 ?
O1 C1 1.280(4) . ?
O2 C1 1.255(4) . ?
O3 C2 1.257(4) . ?
O3 Mn2 2.109(2) 3_566 ?
O4 C2 1.256(4) . ?
O4 Mn1 2.101(2) 3_566 ?
O5 H5C 0.832(10) . ?
O5 H5D 0.841(10) . ?
C1 C3 1.487(4) . ?
C2 C5 1.502(4) . ?
C3 C8 1.388(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C6 C7 1.399(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(4) . ?
C7 C11 1.481(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(4) . ?
C9 C14 1.495(5) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C12 C13 1.385(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Mn1 O5 88.54(11) 3_466 . ?
O4 Mn1 N1 109.86(9) 3_466 8_575 ?
O5 Mn1 N1 99.42(10) . 8_575 ?
O4 Mn1 O2 157.89(8) 3_466 . ?
O5 Mn1 O2 87.00(11) . . ?
N1 Mn1 O2 92.23(8) 8_575 . ?
O4 Mn1 O1 101.70(8) 3_466 . ?
O5 Mn1 O1 84.08(10) . . ?
N1 Mn1 O1 148.29(8) 8_575 . ?
O2 Mn1 O1 56.30(7) . . ?
O4 Mn1 Cl1 88.64(7) 3_466 . ?
O5 Mn1 Cl1 165.20(8) . . ?
N1 Mn1 Cl1 95.20(7) 8_575 . ?
O2 Mn1 Cl1 90.17(7) . . ?
O1 Mn1 Cl1 82.28(6) . . ?
O4 Mn1 H5C 83.4(18) 3_466 . ?
O5 Mn1 H5C 13.8(16) . . ?
N1 Mn1 H5C 89.0(14) 8_575 . ?
O2 Mn1 H5C 96.6(18) . . ?
O1 Mn1 H5C 97.7(15) . . ?
Cl1 Mn1 H5C 171.9(17) . . ?
O3 Mn2 O3 180.00(11) 7_755 3_466 ?
O3 Mn2 O1 86.65(9) 7_755 5_666 ?
O3 Mn2 O1 93.35(9) 3_466 5_666 ?
O3 Mn2 O1 93.35(9) 7_755 . ?
O3 Mn2 O1 86.65(9) 3_466 . ?
O1 Mn2 O1 180.0 5_666 . ?
O3 Mn2 Cl1 89.72(6) 7_755 5_666 ?
O3 Mn2 Cl1 90.28(6) 3_466 5_666 ?
O1 Mn2 Cl1 85.23(6) 5_666 5_666 ?
O1 Mn2 Cl1 94.77(6) . 5_666 ?
O3 Mn2 Cl1 90.28(6) 7_755 . ?
O3 Mn2 Cl1 89.72(6) 3_466 . ?
O1 Mn2 Cl1 94.77(6) 5_666 . ?
O1 Mn2 Cl1 85.23(6) . . ?
Cl1 Mn2 Cl1 180.0 5_666 . ?
Mn1 Cl1 Mn2 83.10(3) . . ?
C13 N1 C9 117.8(3) . . ?
C13 N1 Mn1 114.9(2) . 8_576 ?
C9 N1 Mn1 126.9(2) . 8_576 ?
C1 O1 Mn2 127.3(2) . . ?
C1 O1 Mn1 86.90(16) . . ?
Mn2 O1 Mn1 94.77(7) . . ?
C1 O2 Mn1 96.28(17) . . ?
C2 O3 Mn2 138.72(19) . 3_566 ?
C2 O4 Mn1 123.42(19) . 3_566 ?
Mn1 O5 H5C 25(3) . . ?
Mn1 O5 H5D 121(3) . . ?
H5C O5 H5D 111.5(18) . . ?
O2 C1 O1 120.5(3) . . ?
O2 C1 C3 119.9(3) . . ?
O1 C1 C3 119.7(3) . . ?
O4 C2 O3 125.6(3) . . ?
O4 C2 C5 117.7(3) . . ?
O3 C2 C5 116.7(3) . . ?
C8 C3 C4 119.7(3) . . ?
C8 C3 C1 120.6(3) . . ?
C4 C3 C1 119.7(3) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C2 118.6(2) . . ?
C6 C5 C2 121.7(3) . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 C11 119.2(3) . . ?
C6 C7 C11 121.8(3) . . ?
C3 C8 C7 120.7(3) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
N1 C9 C10 121.1(3) . . ?
N1 C9 C14 118.0(3) . . ?
C10 C9 C14 120.9(3) . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 117.4(3) . . ?
C10 C11 C7 121.4(3) . . ?
C12 C11 C7 121.1(3) . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N1 C13 C12 123.9(3) . . ?
N1 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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 1552727'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N4 Ni3 O16'
_chemical_formula_weight         846.56

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

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

_cell_length_a                   8.0042(2)
_cell_length_b                   11.5133(3)
_cell_length_c                   17.4969(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.2310(10)
_cell_angle_gamma                90
_cell_volume                     1470.36(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8768
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.992
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23417
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2600
_reflns_number_gt                2228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+3.4061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     238
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.052
_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
Ni1 Ni 0.75865(6) -0.21535(3) -0.08851(2) 0.01576(14) Uani 1 1 d . . . . .
Ni2 Ni 1.0000 0.0000 0.0000 0.01605(16) Uani 1 2 d S . P . .
O1 O 0.7646(4) -0.22247(19) 0.02795(14) 0.0224(5) Uani 1 1 d . . . . .
O2 O 0.8828(3) -0.04644(19) 0.07453(14) 0.0203(5) Uani 1 1 d . . . . .
O3 O 0.7222(3) 0.13791(18) 0.29313(14) 0.0209(5) Uani 1 1 d . . . . .
O4 O 0.7516(3) 0.02741(19) 0.39909(13) 0.0176(5) Uani 1 1 d . . . . .
O5 O 1.0388(3) -0.1769(2) -0.02857(14) 0.0223(5) Uani 1 1 d . U . . .
O6 O 1.3246(6) -0.1901(4) -0.0115(3) 0.0777(12) Uani 1 1 d . . . . .
O7 O 1.1203(7) -0.2388(5) -0.1251(3) 0.111(2) Uani 1 1 d . . . . .
O8 O 0.4813(4) -0.2284(2) -0.13401(16) 0.0301(6) Uani 1 1 d D . . . .
H8A H 0.421(5) -0.191(3) -0.1785(15) 0.045 Uiso 1 1 d D U . . .
H8B H 0.425(5) -0.224(4) -0.1022(19) 0.045 Uiso 1 1 d D U . . .
N1 N 0.7732(4) -0.6124(2) 0.37739(17) 0.0204(6) Uani 1 1 d . . . . .
N2 N 1.1626(5) -0.2008(3) -0.0556(2) 0.0385(8) Uani 1 1 d . U . . .
C1 C 0.8074(5) -0.1401(3) 0.07948(19) 0.0161(7) Uani 1 1 d . . . . .
C2 C 0.7715(4) -0.1539(3) 0.15699(19) 0.0150(7) Uani 1 1 d . . . . .
C3 C 0.7586(5) -0.2630(3) 0.1877(2) 0.0168(7) Uani 1 1 d . . . . .
H3 H 0.7594 -0.3285 0.1568 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7445(4) -0.2762(3) 0.26407(19) 0.0152(7) Uani 1 1 d . . . . .
C5 C 0.7335(5) -0.1768(3) 0.30640(19) 0.0152(7) Uani 1 1 d . . . . .
H5 H 0.7210 -0.1836 0.3568 0.018 Uiso 1 1 calc R U . . .
C6 C 0.7409(4) -0.0671(3) 0.27479(19) 0.0143(6) Uani 1 1 d . . . . .
C7 C 0.7635(5) -0.0551(3) 0.20109(19) 0.0164(7) Uani 1 1 d . . . . .
H7 H 0.7733 0.0183 0.1811 0.020 Uiso 1 1 calc R U . . .
C8 C 0.7379(4) 0.0382(3) 0.32408(19) 0.0146(7) Uani 1 1 d . . . . .
C9 C 0.7506(5) -0.3936(3) 0.3014(2) 0.0179(7) Uani 1 1 d . . . . .
C10 C 0.7801(7) -0.4942(3) 0.2660(2) 0.0368(10) Uani 1 1 d . . . . .
H10 H 0.7926 -0.4910 0.2154 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7911(7) -0.5993(3) 0.3054(2) 0.0362(10) Uani 1 1 d . . . . .
H11 H 0.8125 -0.6654 0.2802 0.043 Uiso 1 1 calc R U . . .
C12 C 0.7467(6) -0.5157(3) 0.4134(2) 0.0299(9) Uani 1 1 d . . . . .
C13 C 0.7337(6) -0.4080(3) 0.3763(2) 0.0341(10) Uani 1 1 d . . . . .
H13 H 0.7130 -0.3429 0.4027 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7313(10) -0.5259(4) 0.4954(3) 0.070(2) Uani 1 1 d . . . . .
H14A H 0.7127 -0.4503 0.5137 0.104 Uiso 1 1 calc R U . . .
H14B H 0.6294 -0.5751 0.4889 0.104 Uiso 1 1 calc R U . . .
H14C H 0.8419 -0.5591 0.5363 0.104 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
Ni1 O1 2.021(2) . ?
Ni1 O8 2.033(3) . ?
Ni1 N1 2.088(3) 4_545 ?
Ni1 O5 2.096(2) . ?
Ni1 O3 2.162(2) 4 ?
Ni1 O4 2.173(2) 4 ?
Ni1 C8 2.513(3) 4 ?
Ni1 Ni2 3.1340(4) . ?
Ni2 O2 1.967(2) . ?
Ni2 O2 1.967(2) 3_755 ?
Ni2 O4 2.071(2) 4 ?
Ni2 O4 2.071(2) 2_755 ?
Ni2 O5 2.150(2) 3_755 ?
Ni2 O5 2.150(2) . ?
Ni2 Ni1 3.1340(4) 3_755 ?
O1 C1 1.256(4) . ?
O2 C1 1.256(4) . ?
O3 C8 1.253(4) . ?
O3 Ni1 2.162(2) 4_556 ?
O4 C8 1.277(4) . ?
O4 Ni2 2.071(2) 2_755 ?
O4 Ni1 2.173(2) 4_556 ?
O5 N2 1.291(4) . ?
O6 N2 1.213(5) . ?
O7 N2 1.203(5) . ?
O8 H8A 0.846(10) . ?
O8 H8B 0.847(10) . ?
N1 C11 1.333(4) . ?
N1 C12 1.339(4) . ?
N1 Ni1 2.088(3) 4_546 ?
C1 C2 1.506(4) . ?
C2 C3 1.386(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 C9 1.494(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 C8 1.494(4) . ?
C7 H7 0.9300 . ?
C8 Ni1 2.513(3) 4_556 ?
C9 C10 1.379(5) . ?
C9 C13 1.380(5) . ?
C10 C11 1.378(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.384(5) . ?
C12 C14 1.494(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O8 87.81(10) . . ?
O1 Ni1 N1 105.58(10) . 4_545 ?
O8 Ni1 N1 89.87(12) . 4_545 ?
O1 Ni1 O5 85.79(10) . . ?
O8 Ni1 O5 169.55(10) . . ?
N1 Ni1 O5 99.79(11) 4_545 . ?
O1 Ni1 O3 157.08(9) . 4 ?
O8 Ni1 O3 87.65(10) . 4 ?
N1 Ni1 O3 96.86(9) 4_545 4 ?
O5 Ni1 O3 95.06(9) . 4 ?
O1 Ni1 O4 97.47(8) . 4 ?
O8 Ni1 O4 93.16(10) . 4 ?
N1 Ni1 O4 156.85(10) 4_545 4 ?
O5 Ni1 O4 79.53(9) . 4 ?
O3 Ni1 O4 60.39(8) 4 4 ?
O1 Ni1 C8 127.95(9) . 4 ?
O8 Ni1 C8 91.89(10) . 4 ?
N1 Ni1 C8 126.47(10) 4_545 4 ?
O5 Ni1 C8 85.58(10) . 4 ?
O3 Ni1 C8 29.91(9) 4 4 ?
O4 Ni1 C8 30.55(9) 4 4 ?
O1 Ni1 Ni2 77.24(7) . . ?
O8 Ni1 Ni2 127.20(8) . . ?
N1 Ni1 Ni2 142.88(9) 4_545 . ?
O5 Ni1 Ni2 43.09(6) . . ?
O3 Ni1 Ni2 87.74(6) 4 . ?
O4 Ni1 Ni2 41.16(6) 4 . ?
C8 Ni1 Ni2 62.10(7) 4 . ?
O2 Ni2 O2 180.0 . 3_755 ?
O2 Ni2 O4 88.37(9) . 4 ?
O2 Ni2 O4 91.63(9) 3_755 4 ?
O2 Ni2 O4 91.63(9) . 2_755 ?
O2 Ni2 O4 88.37(9) 3_755 2_755 ?
O4 Ni2 O4 180.00(19) 4 2_755 ?
O2 Ni2 O5 87.12(9) . 3_755 ?
O2 Ni2 O5 92.88(9) 3_755 3_755 ?
O4 Ni2 O5 99.38(9) 4 3_755 ?
O4 Ni2 O5 80.62(9) 2_755 3_755 ?
O2 Ni2 O5 92.88(9) . . ?
O2 Ni2 O5 87.12(9) 3_755 . ?
O4 Ni2 O5 80.62(9) 4 . ?
O4 Ni2 O5 99.38(9) 2_755 . ?
O5 Ni2 O5 180.0 3_755 . ?
O2 Ni2 Ni1 104.61(6) . 3_755 ?
O2 Ni2 Ni1 75.39(6) 3_755 3_755 ?
O4 Ni2 Ni1 136.33(6) 4 3_755 ?
O4 Ni2 Ni1 43.67(6) 2_755 3_755 ?
O5 Ni2 Ni1 41.77(7) 3_755 3_755 ?
O5 Ni2 Ni1 138.23(7) . 3_755 ?
O2 Ni2 Ni1 75.39(6) . . ?
O2 Ni2 Ni1 104.62(6) 3_755 . ?
O4 Ni2 Ni1 43.67(6) 4 . ?
O4 Ni2 Ni1 136.33(6) 2_755 . ?
O5 Ni2 Ni1 138.23(7) 3_755 . ?
O5 Ni2 Ni1 41.77(7) . . ?
Ni1 Ni2 Ni1 180.0 3_755 . ?
C1 O1 Ni1 125.4(2) . . ?
C1 O2 Ni2 130.7(2) . . ?
C8 O3 Ni1 90.78(18) . 4_556 ?
C8 O4 Ni2 122.6(2) . 2_755 ?
C8 O4 Ni1 89.62(18) . 4_556 ?
Ni2 O4 Ni1 95.17(9) 2_755 4_556 ?
N2 O5 Ni1 126.6(2) . . ?
N2 O5 Ni2 119.5(2) . . ?
Ni1 O5 Ni2 95.14(10) . . ?
Ni1 O8 H8A 116(3) . . ?
Ni1 O8 H8B 122(3) . . ?
H8A O8 H8B 108.7(17) . . ?
C11 N1 C12 116.7(3) . . ?
C11 N1 Ni1 114.7(2) . 4_546 ?
C12 N1 Ni1 128.1(2) . 4_546 ?
O7 N2 O6 117.7(4) . . ?
O7 N2 O5 120.5(4) . . ?
O6 N2 O5 121.7(4) . . ?
O2 C1 O1 126.6(3) . . ?
O2 C1 C2 115.3(3) . . ?
O1 C1 C2 118.0(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 118.8(3) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 C9 120.7(3) . . ?
C3 C4 C9 121.2(3) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C8 119.8(3) . . ?
C5 C6 C8 119.6(3) . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O3 C8 O4 119.0(3) . . ?
O3 C8 C6 121.1(3) . . ?
O4 C8 C6 120.0(3) . . ?
O3 C8 Ni1 59.31(15) . 4_556 ?
O4 C8 Ni1 59.83(15) . 4_556 ?
C6 C8 Ni1 175.7(2) . 4_556 ?
C10 C9 C13 115.4(3) . . ?
C10 C9 C4 122.9(3) . . ?
C13 C9 C4 121.7(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N1 C11 C10 124.3(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
N1 C12 C13 121.3(3) . . ?
N1 C12 C14 118.5(3) . . ?
C13 C12 C14 120.1(3) . . ?
C9 C13 C12 122.4(3) . . ?
C9 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O5 N2 O7 7.9(6) . . . . ?
Ni2 O5 N2 O7 -115.4(5) . . . . ?
Ni1 O5 N2 O6 -169.4(3) . . . . ?
Ni2 O5 N2 O6 67.4(5) . . . . ?
Ni2 O2 C1 O1 -11.6(5) . . . . ?
Ni2 O2 C1 C2 166.4(2) . . . . ?
Ni1 O1 C1 O2 -12.9(5) . . . . ?
Ni1 O1 C1 C2 169.1(2) . . . . ?
O2 C1 C2 C3 -154.3(3) . . . . ?
O1 C1 C2 C3 23.9(5) . . . . ?
O2 C1 C2 C7 21.3(4) . . . . ?
O1 C1 C2 C7 -160.4(3) . . . . ?
C7 C2 C3 C4 -2.4(5) . . . . ?
C1 C2 C3 C4 173.2(3) . . . . ?
C2 C3 C4 C5 3.5(5) . . . . ?
C2 C3 C4 C9 -173.5(3) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C9 C4 C5 C6 175.4(3) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C4 C5 C6 C8 -177.0(3) . . . . ?
C5 C6 C7 C2 2.6(5) . . . . ?
C8 C6 C7 C2 178.1(3) . . . . ?
C3 C2 C7 C6 -0.7(5) . . . . ?
C1 C2 C7 C6 -176.4(3) . . . . ?
Ni1 O3 C8 O4 5.0(3) 4_556 . . . ?
Ni1 O3 C8 C6 -175.0(3) 4_556 . . . ?
Ni2 O4 C8 O3 -100.8(3) 2_755 . . . ?
Ni1 O4 C8 O3 -4.9(3) 4_556 . . . ?
Ni2 O4 C8 C6 79.2(3) 2_755 . . . ?
Ni1 O4 C8 C6 175.1(3) 4_556 . . . ?
Ni2 O4 C8 Ni1 -95.89(18) 2_755 . . 4_556 ?
C7 C6 C8 O3 13.1(5) . . . . ?
C5 C6 C8 O3 -171.3(3) . . . . ?
C7 C6 C8 O4 -166.9(3) . . . . ?
C5 C6 C8 O4 8.7(5) . . . . ?
C5 C4 C9 C10 -173.2(4) . . . . ?
C3 C4 C9 C10 3.6(6) . . . . ?
C5 C4 C9 C13 4.2(5) . . . . ?
C3 C4 C9 C13 -178.9(4) . . . . ?
C13 C9 C10 C11 -0.1(6) . . . . ?
C4 C9 C10 C11 177.5(4) . . . . ?
C12 N1 C11 C10 -1.5(7) . . . . ?
Ni1 N1 C11 C10 171.4(4) 4_546 . . . ?
C9 C10 C11 N1 0.7(7) . . . . ?
C11 N1 C12 C13 1.7(6) . . . . ?
Ni1 N1 C12 C13 -170.1(3) 4_546 . . . ?
C11 N1 C12 C14 -178.2(5) . . . . ?
Ni1 N1 C12 C14 10.0(6) 4_546 . . . ?
C10 C9 C13 C12 0.4(6) . . . . ?
C4 C9 C13 C12 -177.3(4) . . . . ?
N1 C12 C13 C9 -1.2(7) . . . . ?
C14 C12 C13 C9 178.7(5) . . . . ?

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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 1552726'
_audit_update_record             
;
2017-05-28 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Co3 N4 O16'
_chemical_formula_weight         847.28

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   18.1510(9)
_cell_length_b                   11.5168(5)
_cell_length_c                   15.9081(8)
_cell_angle_alpha                90
_cell_angle_beta                 117.996(2)
_cell_angle_gamma                90
_cell_volume                     2936.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4737
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             1708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.766
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23188
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2587
_reflns_number_gt                1958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+13.3777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2587
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.16308(3) 0.97577(5) 0.03675(4) 0.01836(17) Uani 1 1 d . . . . .
Co2 Co 0.2500 0.7500 0.0000 0.0185(2) Uani 1 2 d S . P . .
O1 O 0.03777(17) 0.8978(2) -0.0630(2) 0.0251(7) Uani 1 1 d . . . . .
O2 O 0.14579(15) 0.7892(2) 0.01965(19) 0.0182(6) Uani 1 1 d . . . . .
O3 O 0.22693(18) 0.9370(3) -0.0467(2) 0.0270(7) Uani 1 1 d . U . . .
O4 O 0.1246(3) 0.9842(5) -0.1792(3) 0.0812(16) Uani 1 1 d . . . . .
O5 O 0.2430(3) 0.9456(4) -0.1713(3) 0.0641(12) Uani 1 1 d . . . . .
O6 O -0.22090(17) 0.5321(2) -0.3486(2) 0.0249(7) Uani 1 1 d . . . . .
O7 O -0.17823(16) 0.7094(2) -0.36514(19) 0.0211(7) Uani 1 1 d . . . . .
O8 O 0.1162(2) 0.9945(3) 0.1316(3) 0.0345(9) Uani 1 1 d . . . . .
H8A H 0.084(4) 1.028(5) 0.119(5) 0.052 Uiso 1 1 d . U . . .
H8B H 0.147(4) 1.003(5) 0.184(4) 0.052 Uiso 1 1 d . U . . .
N1 N 0.1277(2) 0.1477(3) -0.0098(3) 0.0243(8) Uani 1 1 d . . . . .
N2 N 0.1987(3) 0.9552(3) -0.1302(4) 0.0373(10) Uani 1 1 d . U . . .
C1 C 0.0702(2) 0.7991(3) -0.0443(3) 0.0141(8) Uani 1 1 d . . . . .
C2 C 0.0231(2) 0.6936(3) -0.0953(3) 0.0134(8) Uani 1 1 d . . . . .
C3 C -0.0501(2) 0.7044(3) -0.1795(3) 0.0144(8) Uani 1 1 d . . . . .
H3A H -0.0704 0.7774 -0.2046 0.017 Uiso 1 1 calc R U . . .
C4 C -0.0932(2) 0.6049(3) -0.2267(3) 0.0120(8) Uani 1 1 d . . . . .
C5 C -0.0621(2) 0.4964(3) -0.1894(3) 0.0146(9) Uani 1 1 d . . . . .
H5A H -0.0927 0.4305 -0.2197 0.017 Uiso 1 1 calc R U . . .
C6 C 0.0139(2) 0.4839(3) -0.1076(3) 0.0156(8) Uani 1 1 d . . . . .
C7 C 0.0555(2) 0.5846(3) -0.0603(3) 0.0142(8) Uani 1 1 d . . . . .
H7A H 0.1057 0.5785 -0.0044 0.017 Uiso 1 1 calc R U . . .
C8 C -0.1709(2) 0.6155(3) -0.3207(3) 0.0147(8) Uani 1 1 d . . . . .
C9 C 0.0518(2) 0.3677(3) -0.0731(3) 0.0169(9) Uani 1 1 d . . . . .
C10 C 0.1244(3) 0.3529(4) 0.0109(3) 0.0238(10) Uani 1 1 d . . . . .
H10A H 0.1496 0.4176 0.0486 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1611(3) 0.2452(4) 0.0412(3) 0.0251(10) Uani 1 1 d . . . . .
C12 C 0.0568(3) 0.1617(4) -0.0915(3) 0.0329(12) Uani 1 1 d . . . . .
H12A H 0.0325 0.0960 -0.1281 0.039 Uiso 1 1 calc R U . . .
C13 C 0.0177(3) 0.2669(4) -0.1248(3) 0.0304(11) Uani 1 1 d . . . . .
H13A H -0.0316 0.2703 -0.1819 0.037 Uiso 1 1 calc R U . . .
C14 C 0.2408(3) 0.2333(4) 0.1343(4) 0.0469(16) Uani 1 1 d . . . . .
H14A H 0.2578 0.3083 0.1633 0.070 Uiso 1 1 calc R U . . .
H14B H 0.2312 0.1829 0.1763 0.070 Uiso 1 1 calc R U . . .
H14C H 0.2838 0.2011 0.1224 0.070 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 O6 2.040(3) 8_566 ?
Co1 O8 2.063(4) . ?
Co1 N1 2.106(3) 1_565 ?
Co1 O2 2.170(3) . ?
Co1 O3 2.180(3) . ?
Co1 O1 2.260(3) . ?
Co2 O7 1.974(3) 8_566 ?
Co2 O7 1.974(3) 2_554 ?
Co2 O2 2.106(3) . ?
Co2 O2 2.106(3) 7_565 ?
Co2 O3 2.252(3) . ?
Co2 O3 2.252(3) 7_565 ?
O1 C1 1.249(5) . ?
O2 C1 1.273(4) . ?
O3 N2 1.196(5) . ?
O4 N2 1.243(6) . ?
O5 N2 1.257(6) . ?
O6 C8 1.251(5) . ?
O6 Co1 2.040(3) 8_465 ?
O7 C8 1.263(5) . ?
O7 Co2 1.974(3) 2_554 ?
O8 H8A 0.65(6) . ?
O8 H8B 0.76(6) . ?
N1 C12 1.342(5) . ?
N1 C11 1.350(5) . ?
N1 Co1 2.106(3) 1_545 ?
C1 C2 1.488(5) . ?
C2 C3 1.380(5) . ?
C2 C7 1.388(5) . ?
C3 C4 1.392(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(5) . ?
C4 C8 1.503(5) . ?
C5 C6 1.390(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.395(5) . ?
C6 C9 1.486(5) . ?
C7 H7A 0.9300 . ?
C9 C10 1.378(6) . ?
C9 C13 1.390(6) . ?
C10 C11 1.383(6) . ?
C10 H10A 0.9300 . ?
C11 C14 1.515(6) . ?
C12 C13 1.378(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Co1 O8 87.59(13) 8_566 . ?
O6 Co1 N1 111.87(13) 8_566 1_565 ?
O8 Co1 N1 89.79(15) . 1_565 ?
O6 Co1 O2 95.49(10) 8_566 . ?
O8 Co1 O2 96.32(13) . . ?
N1 Co1 O2 152.21(12) 1_565 . ?
O6 Co1 O3 85.09(12) 8_566 . ?
O8 Co1 O3 170.82(13) . . ?
N1 Co1 O3 98.08(14) 1_565 . ?
O2 Co1 O3 78.91(11) . . ?
O6 Co1 O1 152.37(11) 8_566 . ?
O8 Co1 O1 85.99(13) . . ?
N1 Co1 O1 94.96(12) 1_565 . ?
O2 Co1 O1 58.67(10) . . ?
O3 Co1 O1 97.97(11) . . ?
O7 Co2 O7 180.0 8_566 2_554 ?
O7 Co2 O2 88.19(11) 8_566 . ?
O7 Co2 O2 91.81(11) 2_554 . ?
O7 Co2 O2 91.81(11) 8_566 7_565 ?
O7 Co2 O2 88.19(11) 2_554 7_565 ?
O2 Co2 O2 180.0 . 7_565 ?
O7 Co2 O3 93.30(11) 8_566 . ?
O7 Co2 O3 86.70(11) 2_554 . ?
O2 Co2 O3 78.66(11) . . ?
O2 Co2 O3 101.34(11) 7_565 . ?
O7 Co2 O3 86.70(11) 8_566 7_565 ?
O7 Co2 O3 93.30(11) 2_554 7_565 ?
O2 Co2 O3 101.34(11) . 7_565 ?
O2 Co2 O3 78.66(11) 7_565 7_565 ?
O3 Co2 O3 180.0 . 7_565 ?
C1 O1 Co1 89.3(2) . . ?
C1 O2 Co2 127.4(3) . . ?
C1 O2 Co1 92.8(2) . . ?
Co2 O2 Co1 98.26(11) . . ?
N2 O3 Co1 124.5(3) . . ?
N2 O3 Co2 116.8(3) . . ?
Co1 O3 Co2 93.70(12) . . ?
C8 O6 Co1 128.6(3) . 8_465 ?
C8 O7 Co2 130.8(2) . 2_554 ?
Co1 O8 H8A 118(6) . . ?
Co1 O8 H8B 118(5) . . ?
H8A O8 H8B 110(7) . . ?
C12 N1 C11 116.0(4) . . ?
C12 N1 Co1 116.7(3) . 1_545 ?
C11 N1 Co1 126.4(3) . 1_545 ?
O3 N2 O4 121.1(5) . . ?
O3 N2 O5 121.1(4) . . ?
O4 N2 O5 117.7(5) . . ?
O1 C1 O2 118.8(3) . . ?
O1 C1 C2 121.8(3) . . ?
O2 C1 C2 119.3(3) . . ?
C3 C2 C7 120.3(3) . . ?
C3 C2 C1 120.1(4) . . ?
C7 C2 C1 119.5(3) . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 C8 120.2(3) . . ?
C3 C4 C8 119.8(3) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 117.9(3) . . ?
C5 C6 C9 121.5(3) . . ?
C7 C6 C9 120.6(3) . . ?
C2 C7 C6 121.0(3) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
O6 C8 O7 126.2(3) . . ?
O6 C8 C4 118.4(3) . . ?
O7 C8 C4 115.4(3) . . ?
C10 C9 C13 115.3(4) . . ?
C10 C9 C6 122.4(4) . . ?
C13 C9 C6 122.2(4) . . ?
C9 C10 C11 122.3(4) . . ?
C9 C10 H10A 118.9 . . ?
C11 C10 H10A 118.9 . . ?
N1 C11 C10 122.0(4) . . ?
N1 C11 C14 117.7(4) . . ?
C10 C11 C14 120.3(4) . . ?
N1 C12 C13 124.4(4) . . ?
N1 C12 H12A 117.8 . . ?
C13 C12 H12A 117.8 . . ?
C12 C13 C9 120.1(4) . . ?
C12 C13 H13A 120.0 . . ?
C9 C13 H13A 120.0 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.095

