# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1456726'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 N4 Ni3 O12'
_chemical_formula_weight         802.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0024 0.0012 '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 0.0047 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0086 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3524 0.9030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.479(2)
_cell_length_b                   10.789(2)
_cell_length_c                   13.770(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.00(3)
_cell_angle_gamma                90
_cell_volume                     1569.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    44804
_cell_measurement_theta_min      0.36
_cell_measurement_theta_max      29.48

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.329
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   'HKL3000 Scalepack'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      102(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22005
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         29.482
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             6179
_reflns_number_gt                5971
_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       'PAL ADSC Quantum-210 ADX Program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WinGX

_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)+(0.0455P)²+0.9867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6179
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.35180(2) 0.10229(2) 0.12775(2) 0.00795(4) Uani 1 1 d . . . . .
Ni2 Ni 0.5000 0.0000 0.0000 0.00897(5) Uani 1 2 d S . P . .
N1 N 0.17051(8) 0.15667(8) 0.10507(7) 0.01085(14) Uani 1 1 d . . . . .
N2 N 0.37502(8) 0.29707(8) 0.12433(7) 0.01062(14) Uani 1 1 d . . . . .
C1 C 0.07737(10) 0.07976(10) 0.10242(8) 0.01343(16) Uani 1 1 d . . . . .
H1 H 0.0922 -0.0070 0.1043 0.016 Uiso 1 1 calc R U . . .
C2 C -0.03950(10) 0.12103(12) 0.09702(9) 0.01711(18) Uani 1 1 d . . . . .
H2 H -0.1042 0.0640 0.0931 0.021 Uiso 1 1 calc R U . . .
C3 C -0.05936(11) 0.24825(12) 0.09744(10) 0.0192(2) Uani 1 1 d . . . . .
H3 H -0.1374 0.2797 0.0957 0.023 Uiso 1 1 calc R U . . .
C4 C 0.03624(11) 0.32841(11) 0.10037(9) 0.01688(18) Uani 1 1 d . . . . .
H4 H 0.0245 0.4156 0.1004 0.020 Uiso 1 1 calc R U . . .
C5 C 0.15001(9) 0.27948(9) 0.10330(8) 0.01161(15) Uani 1 1 d . . . . .
C6 C 0.25423(10) 0.36353(9) 0.10233(9) 0.01390(17) Uani 1 1 d . . . . .
H6A H 0.2271 0.4040 0.0324 0.017 Uiso 1 1 calc R U . . .
H6B H 0.2685 0.4293 0.1559 0.017 Uiso 1 1 calc R U . . .
C7 C 0.41979(11) 0.31390(9) 0.03775(8) 0.01372(16) Uani 1 1 d . . . . .
H7A H 0.5105 0.2919 0.0624 0.016 Uiso 1 1 calc R U . . .
H7B H 0.4095 0.4015 0.0144 0.016 Uiso 1 1 calc R U . . .
C8 C 0.34127(11) 0.22968(10) -0.05355(8) 0.01464(17) Uani 1 1 d . . . . .
H8A H 0.2522 0.2581 -0.0828 0.018 Uiso 1 1 calc R U . . .
H8B H 0.3738 0.2347 -0.1103 0.018 Uiso 1 1 calc R U . . .
C9 C 0.46999(10) 0.32672(9) 0.23014(8) 0.01229(16) Uani 1 1 d . . . . .
H9A H 0.4764 0.4177 0.2402 0.015 Uiso 1 1 calc R U . . .
H9B H 0.5539 0.2949 0.2374 0.015 Uiso 1 1 calc R U . . .
C10 C 0.43079(10) 0.26741(9) 0.31327(8) 0.01279(16) Uani 1 1 d . . . . .
H10A H 0.4987 0.2797 0.3840 0.015 Uiso 1 1 calc R U . . .
H10B H 0.3532 0.3083 0.3125 0.015 Uiso 1 1 calc R U . . .
C11 C 0.35474(9) -0.16359(9) 0.09229(8) 0.00996(15) Uani 1 1 d . . . . .
C12 C 0.34082(11) -0.29760(10) 0.11937(9) 0.01597(18) Uani 1 1 d . . . . .
H12A H 0.3452 -0.3517 0.0637 0.024 Uiso 1 1 calc R U . . .
H12B H 0.2590 -0.3088 0.1251 0.024 Uiso 1 1 calc R U . . .
H12C H 0.4092 -0.3189 0.1867 0.024 Uiso 1 1 calc R U . . .
C13 C 0.63556(9) 0.03381(9) 0.24927(8) 0.01204(16) Uani 1 1 d . . . . .
C14 C 0.76412(12) 0.00678(18) 0.24956(12) 0.0327(4) Uani 1 1 d . . . . .
H14A H 0.8126 0.0840 0.2605 0.049 Uiso 1 1 calc R U . . .
H14B H 0.7547 -0.0299 0.1818 0.049 Uiso 1 1 calc R U . . .
H14C H 0.8089 -0.0514 0.3066 0.049 Uiso 1 1 calc R U . . .
O1 O 0.34675(8) 0.10562(6) -0.01933(6) 0.01093(13) Uani 1 1 d . . . . .
O2 O 0.40748(7) 0.13731(7) 0.29372(6) 0.01171(12) Uani 1 1 d . . . . .
H2O H 0.4763 0.0985 0.3191 0.034(6) Uiso 1 1 calc R . . . .
O3 O 0.31892(7) -0.08022(7) 0.13963(6) 0.01129(12) Uani 1 1 d . . . . .
O4 O 0.40252(8) -0.14605(7) 0.02560(6) 0.01413(14) Uani 1 1 d . . . . .
O5 O 0.62417(8) 0.03780(8) 0.33638(6) 0.01472(14) Uani 1 1 d . . . . .
O6 O 0.54535(7) 0.05617(7) 0.16075(6) 0.01094(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.0036(9) . ?
Ni1 O3 2.0236(8) . ?
Ni1 N1 2.0651(10) . ?
Ni1 N2 2.1211(10) . ?
Ni1 O6 2.1451(9) . ?
Ni1 O2 2.1524(9) . ?
Ni2 O1 2.0244(8) 3_655 ?
Ni2 O1 2.0244(8) . ?
Ni2 O4 2.0415(8) . ?
Ni2 O4 2.0415(8) 3_655 ?
Ni2 O6 2.1535(9) . ?
Ni2 O6 2.1535(9) 3_655 ?
N1 C1 1.3426(14) . ?
N1 C5 1.3442(13) . ?
N2 C9 1.4739(14) . ?
N2 C7 1.4823(14) . ?
N2 C6 1.4833(14) . ?
C1 C2 1.3876(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.3918(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3854(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3945(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.5055(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5274(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.4123(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5248(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2 1.4346(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O4 1.2544(12) . ?
C11 O3 1.2698(12) . ?
C11 C12 1.5170(15) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O5 1.2571(13) . ?
C13 O6 1.2766(13) . ?
C13 C14 1.5027(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O2 H2O 0.8400 . ?

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 O3 99.58(3) . . ?
O1 Ni1 N1 102.28(4) . . ?
O3 Ni1 N1 94.58(3) . . ?
O1 Ni1 N2 85.07(3) . . ?
O3 Ni1 N2 174.20(3) . . ?
N1 Ni1 N2 80.97(4) . . ?
O1 Ni1 O6 80.61(4) . . ?
O3 Ni1 O6 88.14(3) . . ?
N1 Ni1 O6 175.62(3) . . ?
N2 Ni1 O6 96.07(3) . . ?
O1 Ni1 O2 161.70(3) . . ?
O3 Ni1 O2 94.15(3) . . ?
N1 Ni1 O2 88.53(4) . . ?
N2 Ni1 O2 82.06(3) . . ?
O6 Ni1 O2 87.85(4) . . ?
O1 Ni2 O1 180.00(4) 3_655 . ?
O1 Ni2 O4 92.84(4) 3_655 . ?
O1 Ni2 O4 87.16(3) . . ?
O1 Ni2 O4 87.16(4) 3_655 3_655 ?
O1 Ni2 O4 92.84(3) . 3_655 ?
O4 Ni2 O4 180.0 . 3_655 ?
O1 Ni2 O6 100.06(4) 3_655 . ?
O1 Ni2 O6 79.94(4) . . ?
O4 Ni2 O6 88.19(3) . . ?
O4 Ni2 O6 91.81(3) 3_655 . ?
O1 Ni2 O6 79.94(4) 3_655 3_655 ?
O1 Ni2 O6 100.06(4) . 3_655 ?
O4 Ni2 O6 91.81(3) . 3_655 ?
O4 Ni2 O6 88.19(3) 3_655 3_655 ?
O6 Ni2 O6 179.999(15) . 3_655 ?
C1 N1 C5 118.47(9) . . ?
C1 N1 Ni1 124.98(7) . . ?
C5 N1 Ni1 116.21(7) . . ?
C9 N2 C7 114.43(8) . . ?
C9 N2 C6 111.61(8) . . ?
C7 N2 C6 111.51(8) . . ?
C9 N2 Ni1 104.12(6) . . ?
C7 N2 Ni1 103.02(6) . . ?
C6 N2 Ni1 111.59(6) . . ?
N1 C1 C2 123.10(10) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.21(11) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 119.12(10) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.12(10) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.94(10) . . ?
N1 C5 C6 117.38(9) . . ?
C4 C5 C6 120.67(9) . . ?
N2 C6 C5 112.93(8) . . ?
N2 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 C8 108.10(8) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O1 C8 C7 110.74(8) . . ?
O1 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 C10 109.26(8) . . ?
N2 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
O2 C10 C9 110.97(8) . . ?
O2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
O2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O4 C11 O3 126.22(9) . . ?
O4 C11 C12 116.22(9) . . ?
O3 C11 C12 117.56(9) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O6 123.82(9) . . ?
O5 C13 C14 118.18(10) . . ?
O6 C13 C14 117.94(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 O1 Ni1 109.53(6) . . ?
C8 O1 Ni2 120.03(7) . . ?
Ni1 O1 Ni2 100.17(4) . . ?
C10 O2 Ni1 109.10(6) . . ?
C10 O2 H2O 109.5 . . ?
Ni1 O2 H2O 101.3 . . ?
C11 O3 Ni1 122.67(7) . . ?
C11 O4 Ni2 131.97(7) . . ?
C13 O6 Ni1 129.25(7) . . ?
C13 O6 Ni2 135.10(7) . . ?
Ni1 O6 Ni2 91.90(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
C5 N1 C1 C2 0.58(15) . . . . ?
Ni1 N1 C1 C2 173.68(8) . . . . ?
N1 C1 C2 C3 -1.90(17) . . . . ?
C1 C2 C3 C4 1.69(17) . . . . ?
C2 C3 C4 C5 -0.29(17) . . . . ?
C1 N1 C5 C4 0.95(15) . . . . ?
Ni1 N1 C5 C4 -172.76(8) . . . . ?
C1 N1 C5 C6 -177.82(9) . . . . ?
Ni1 N1 C5 C6 8.48(12) . . . . ?
C3 C4 C5 N1 -1.08(16) . . . . ?
C3 C4 C5 C6 177.64(10) . . . . ?
C9 N2 C6 C5 -107.81(10) . . . . ?
C7 N2 C6 C5 122.82(9) . . . . ?
Ni1 N2 C6 C5 8.22(10) . . . . ?
N1 C5 C6 N2 -11.14(13) . . . . ?
C4 C5 C6 N2 170.08(9) . . . . ?
C9 N2 C7 C8 155.10(8) . . . . ?
C6 N2 C7 C8 -77.04(10) . . . . ?
Ni1 N2 C7 C8 42.77(9) . . . . ?
N2 C7 C8 O1 -54.97(11) . . . . ?
C7 N2 C9 C10 -161.60(8) . . . . ?
C6 N2 C9 C10 70.59(10) . . . . ?
Ni1 N2 C9 C10 -49.93(8) . . . . ?
N2 C9 C10 O2 53.23(11) . . . . ?
C7 C8 O1 Ni1 35.86(10) . . . . ?
C7 C8 O1 Ni2 -79.06(10) . . . . ?
C9 C10 O2 Ni1 -26.69(9) . . . . ?
O4 C11 O3 Ni1 -7.35(15) . . . . ?
C12 C11 O3 Ni1 171.66(7) . . . . ?
O3 C11 O4 Ni2 24.91(16) . . . . ?
C12 C11 O4 Ni2 -154.11(8) . . . . ?
O5 C13 O6 Ni1 -1.33(15) . . . . ?
C14 C13 O6 Ni1 -178.48(10) . . . . ?
O5 C13 O6 Ni2 -153.04(8) . . . . ?
C14 C13 O6 Ni2 29.82(16) . . . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1456727'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 Co3 N4 O12'
_chemical_formula_weight         803.45

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.6737(12)
_cell_length_b                   10.8739(12)
_cell_length_c                   13.8627(15)
_cell_angle_alpha                90
_cell_angle_beta                 112.781(2)
_cell_angle_gamma                90
_cell_volume                     1622.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4817
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             830
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_T_max  0.642
_exptl_absorpt_process_details   '(SADABSA; Bruker, ver 2.03.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11458
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4020
_reflns_number_gt                2699
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WINGX

_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)+(0.0680P)²+7.4910P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4020
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1982
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.84726(7) 0.59649(6) 0.12692(6) 0.0292(2) Uani 1 1 d . . . . .
Co2 Co 1.0000 0.5000 0.0000 0.0326(3) Uani 1 2 d S . P . .
N1 N 0.6674(4) 0.6586(4) 0.1058(4) 0.0342(10) Uani 1 1 d . . . . .
N2 N 0.8706(4) 0.7967(4) 0.1238(3) 0.0306(9) Uani 1 1 d . . . . .
O1 O 0.8544(4) 0.6084(3) -0.0137(3) 0.0345(8) Uani 1 1 d . . . . .
O2 O 0.9121(4) 0.6362(4) 0.2914(3) 0.0343(8) Uani 1 1 d . . . . .
H2O H 0.9736 0.6074 0.2817 0.041 Uiso 1 1 calc R U . . .
C1 C 0.5752(5) 0.5832(6) 0.1035(5) 0.0376(12) Uani 1 1 d . . . . .
H1 H 0.5882 0.4969 0.1047 0.045 Uiso 1 1 calc R U . . .
C2 C 0.4622(6) 0.6262(6) 0.0996(5) 0.0436(14) Uani 1 1 d . . . . .
H2 H 0.3981 0.5704 0.0961 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4439(6) 0.7507(7) 0.1007(5) 0.0477(16) Uani 1 1 d . . . . .
H3 H 0.3677 0.7827 0.0997 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5383(6) 0.8283(6) 0.1033(5) 0.0443(14) Uani 1 1 d . . . . .
H4 H 0.5279 0.9149 0.1042 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6483(5) 0.7792(5) 0.1047(4) 0.0363(12) Uani 1 1 d . . . . .
C6 C 0.7522(6) 0.8625(5) 0.1030(5) 0.0404(13) Uani 1 1 d . . . . .
H6A H 0.7254 0.9028 0.0337 0.049 Uiso 1 1 calc R U . . .
H6B H 0.7668 0.9278 0.1563 0.049 Uiso 1 1 calc R U . . .
C7 C 0.9146(6) 0.8167(5) 0.0375(5) 0.0389(13) Uani 1 1 d . . . . .
H7A H 1.0046 0.7992 0.0623 0.047 Uiso 1 1 calc R U . . .
H7B H 0.9003 0.9032 0.0135 0.047 Uiso 1 1 calc R U . . .
C8 C 0.8424(6) 0.7308(5) -0.0513(4) 0.0380(13) Uani 1 1 d . . . . .
H8A H 0.7537 0.7547 -0.0809 0.046 Uiso 1 1 calc R U . . .
H8B H 0.8747 0.7367 -0.1075 0.046 Uiso 1 1 calc R U . . .
C9 C 0.9642(5) 0.8273(5) 0.2282(4) 0.0350(12) Uani 1 1 d . . . . .
H9A H 0.9678 0.9175 0.2385 0.042 Uiso 1 1 calc R U . . .
H9B H 1.0472 0.7987 0.2340 0.042 Uiso 1 1 calc R U . . .
C10 C 0.9293(6) 0.7651(5) 0.3114(4) 0.0366(12) Uani 1 1 d . . . . .
H10A H 0.9958 0.7788 0.3812 0.044 Uiso 1 1 calc R U . . .
H10B H 0.8517 0.8017 0.3114 0.044 Uiso 1 1 calc R U . . .
O3 O 0.8137(4) 0.4126(3) 0.1342(3) 0.0326(8) Uani 1 1 d . . . . .
O4 O 0.8967(4) 0.3508(4) 0.0214(3) 0.0422(10) Uani 1 1 d . . . . .
O5 O 1.1269(4) 0.5414(4) 0.3397(3) 0.0399(9) Uani 1 1 d . . . . .
O6 O 1.0466(3) 0.5444(4) 0.1654(3) 0.0347(8) Uani 1 1 d . . . . .
C11 C 0.8501(5) 0.3306(5) 0.0880(5) 0.0327(12) Uani 1 1 d . . . . .
C12 C 0.8387(6) 0.1993(5) 0.1155(5) 0.0417(14) Uani 1 1 d . . . . .
H12A H 0.8482 0.1454 0.0624 0.063 Uiso 1 1 calc R U . . .
H12B H 0.7568 0.1860 0.1180 0.063 Uiso 1 1 calc R U . . .
H12C H 0.9036 0.1806 0.1840 0.063 Uiso 1 1 calc R U . . .
C13 C 1.1363(5) 0.5281(5) 0.2525(5) 0.0351(12) Uani 1 1 d . . . . .
C14 C 1.2615(7) 0.4945(9) 0.2545(6) 0.068(2) Uani 1 1 d . . . . .
H14A H 1.3155 0.5671 0.2729 0.102 Uiso 1 1 calc R U . . .
H14B H 1.2529 0.4647 0.1853 0.102 Uiso 1 1 calc R U . . .
H14C H 1.2982 0.4297 0.3065 0.102 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 O1 1.987(4) . ?
Co1 O3 2.048(4) . ?
Co1 N1 2.115(5) . ?
Co1 O2 2.150(4) . ?
Co1 N2 2.196(4) . ?
Co1 O6 2.250(4) . ?
Co2 O1 2.016(4) . ?
Co2 O1 2.016(4) 3_765 ?
Co2 O4 2.110(4) . ?
Co2 O4 2.110(4) 3_765 ?
Co2 O6 2.196(4) 3_765 ?
Co2 O6 2.196(4) . ?
N1 C5 1.329(7) . ?
N1 C1 1.344(7) . ?
N2 C9 1.474(7) . ?
N2 C6 1.482(7) . ?
N2 C7 1.488(7) . ?
O1 C8 1.416(6) . ?
O2 C10 1.427(7) . ?
O2 H2O 0.8400 . ?
C1 C2 1.379(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.521(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.515(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O3 C11 1.264(6) . ?
O4 C11 1.259(7) . ?
O5 C13 1.263(7) . ?
O6 C13 1.268(7) . ?
C11 C12 1.497(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.496(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O3 101.17(15) . . ?
O1 Co1 N1 105.05(17) . . ?
O3 Co1 N1 96.89(17) . . ?
O1 Co1 O2 153.63(16) . . ?
O3 Co1 O2 98.01(15) . . ?
N1 Co1 O2 90.32(16) . . ?
O1 Co1 N2 82.15(16) . . ?
O3 Co1 N2 175.14(16) . . ?
N1 Co1 N2 78.74(17) . . ?
O2 Co1 N2 79.99(15) . . ?
O1 Co1 O6 79.44(15) . . ?
O3 Co1 O6 86.71(15) . . ?
N1 Co1 O6 173.49(17) . . ?
O2 Co1 O6 83.80(14) . . ?
N2 Co1 O6 97.43(16) . . ?
O1 Co2 O1 180.00(16) . 3_765 ?
O1 Co2 O4 87.47(16) . . ?
O1 Co2 O4 92.53(16) 3_765 . ?
O1 Co2 O4 92.54(16) . 3_765 ?
O1 Co2 O4 87.46(16) 3_765 3_765 ?
O4 Co2 O4 180.0 . 3_765 ?
O1 Co2 O6 99.86(15) . 3_765 ?
O1 Co2 O6 80.14(15) 3_765 3_765 ?
O4 Co2 O6 93.09(15) . 3_765 ?
O4 Co2 O6 86.91(15) 3_765 3_765 ?
O1 Co2 O6 80.14(15) . . ?
O1 Co2 O6 99.86(15) 3_765 . ?
O4 Co2 O6 86.91(15) . . ?
O4 Co2 O6 93.09(15) 3_765 . ?
O6 Co2 O6 180.0 3_765 . ?
C5 N1 C1 118.1(5) . . ?
C5 N1 Co1 118.0(4) . . ?
C1 N1 Co1 123.5(4) . . ?
C9 N2 C6 111.3(4) . . ?
C9 N2 C7 113.6(4) . . ?
C6 N2 C7 111.0(4) . . ?
C9 N2 Co1 104.8(3) . . ?
C6 N2 Co1 111.6(3) . . ?
C7 N2 Co1 104.2(3) . . ?
C8 O1 Co1 112.8(3) . . ?
C8 O1 Co2 122.9(4) . . ?
Co1 O1 Co2 102.92(17) . . ?
C10 O2 Co1 111.6(3) . . ?
C10 O2 H2O 109.5 . . ?
Co1 O2 H2O 74.2 . . ?
N1 C1 C2 122.6(6) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.6(6) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 119.5(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.1(6) . . ?
N1 C5 C6 117.1(5) . . ?
C4 C5 C6 120.7(5) . . ?
N2 C6 C5 113.5(5) . . ?
N2 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C8 107.9(5) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O1 C8 C7 109.6(4) . . ?
O1 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O1 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C10 109.2(4) . . ?
N2 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
O2 C10 C9 110.3(4) . . ?
O2 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
O2 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C11 O3 Co1 123.7(3) . . ?
C11 O4 Co2 132.1(4) . . ?
C13 O6 Co2 138.0(4) . . ?
C13 O6 Co1 131.2(3) . . ?
Co2 O6 Co1 89.56(14) . . ?
O4 C11 O3 125.1(5) . . ?
O4 C11 C12 117.3(5) . . ?
O3 C11 C12 117.6(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O6 123.3(5) . . ?
O5 C13 C14 117.2(5) . . ?
O6 C13 C14 119.5(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 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
C5 N1 C1 C2 0.4(9) . . . . ?
Co1 N1 C1 C2 173.7(4) . . . . ?
N1 C1 C2 C3 -1.7(9) . . . . ?
C1 C2 C3 C4 1.5(10) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C1 N1 C5 C4 1.2(9) . . . . ?
Co1 N1 C5 C4 -172.5(4) . . . . ?
C1 N1 C5 C6 -177.7(5) . . . . ?
Co1 N1 C5 C6 8.6(7) . . . . ?
C3 C4 C5 N1 -1.4(10) . . . . ?
C3 C4 C5 C6 177.4(6) . . . . ?
C9 N2 C6 C5 -108.2(5) . . . . ?
C7 N2 C6 C5 124.2(5) . . . . ?
Co1 N2 C6 C5 8.4(6) . . . . ?
N1 C5 C6 N2 -11.4(8) . . . . ?
C4 C5 C6 N2 169.7(5) . . . . ?
C9 N2 C7 C8 153.6(5) . . . . ?
C6 N2 C7 C8 -80.1(6) . . . . ?
Co1 N2 C7 C8 40.2(5) . . . . ?
Co1 O1 C8 C7 40.0(6) . . . . ?
Co2 O1 C8 C7 -84.1(5) . . . . ?
N2 C7 C8 O1 -54.5(6) . . . . ?
C6 N2 C9 C10 72.7(5) . . . . ?
C7 N2 C9 C10 -161.1(4) . . . . ?
Co1 N2 C9 C10 -48.1(5) . . . . ?
Co1 O2 C10 C9 -30.0(5) . . . . ?
N2 C9 C10 O2 53.9(6) . . . . ?
Co2 O4 C11 O3 28.7(9) . . . . ?
Co2 O4 C11 C12 -150.5(4) . . . . ?
Co1 O3 C11 O4 -9.7(8) . . . . ?
Co1 O3 C11 C12 169.4(4) . . . . ?
Co2 O6 C13 O5 -164.1(4) . . . . ?
Co1 O6 C13 O5 -1.0(9) . . . . ?
Co2 O6 C13 C14 17.6(9) . . . . ?
Co1 O6 C13 C14 -179.4(5) . . . . ?

_refine_diff_density_max         1.371
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.181

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1456728'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H48 Co3 N4 O12'
_chemical_formula_weight         857.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0024 0.0012 '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 0.0047 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3391 0.7736 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0086 0.0047 '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                   7.9190(16)
_cell_length_b                   23.274(5)
_cell_length_c                   9.4900(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.12(3)
_cell_angle_gamma                90
_cell_volume                     1744.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    37930
_cell_measurement_theta_min      0.36
_cell_measurement_theta_max      29.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             890
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.060
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'HKL3000 Scalepack'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21064
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.551
_diffrn_reflns_theta_max         29.431
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             5861
_reflns_number_gt                4241
_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       'PAL ADSC Quantum-210 ADX Program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WINGX

_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)+(0.0747P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5861
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 -0.00348(3) 0.62237(2) 0.60059(3) 0.01874(9) Uani 1 1 d . . . . .
Co2 Co 0.0000 0.5000 0.5000 0.01796(10) Uani 1 2 d S . P . .
N1 N 0.1393(2) 0.69004(7) 0.5921(2) 0.0226(4) Uani 1 1 d . . . . .
N2 N -0.1340(2) 0.65624(7) 0.4411(2) 0.0241(4) Uani 1 1 d . . . . .
O1 O -0.15891(18) 0.56018(6) 0.58204(15) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.12169(18) 0.58184(6) 0.47044(15) 0.0209(3) Uani 1 1 d . . . . .
C1 C 0.2959(3) 0.69676(9) 0.6519(3) 0.0274(5) Uani 1 1 d . . . . .
H1 H 0.3431 0.6675 0.7125 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3923(3) 0.74572(10) 0.6277(3) 0.0332(5) Uani 1 1 d . . . . .
H2 H 0.5029 0.7502 0.6721 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3220(3) 0.78755(10) 0.5373(3) 0.0365(6) Uani 1 1 d . . . . .
H3 H 0.3859 0.8206 0.5163 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1583(3) 0.78086(9) 0.4777(3) 0.0314(5) Uani 1 1 d . . . . .
H4 H 0.1082 0.8097 0.4173 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0684(3) 0.73170(8) 0.5071(2) 0.0259(4) Uani 1 1 d . . . . .
C6 C -0.1093(3) 0.71959(9) 0.4507(3) 0.0285(5) Uani 1 1 d . . . . .
H6A H -0.1900 0.7364 0.5142 0.034 Uiso 1 1 calc R U . . .
H6B H -0.1305 0.7372 0.3561 0.034 Uiso 1 1 calc R U . . .
C7 C -0.3122(3) 0.63891(10) 0.4583(3) 0.0281(5) Uani 1 1 d . . . . .
H7A H -0.3810 0.6441 0.3679 0.034 Uiso 1 1 calc R U . . .
H7B H -0.3608 0.6633 0.5306 0.034 Uiso 1 1 calc R U . . .
C8 C -0.3154(3) 0.57526(9) 0.5039(2) 0.0254(4) Uani 1 1 d . . . . .
H8 H -0.3280 0.5508 0.4170 0.030 Uiso 1 1 calc R U . . .
C9 C -0.4643(3) 0.56361(10) 0.5919(3) 0.0325(5) Uani 1 1 d . . . . .
H9A H -0.4630 0.5232 0.6209 0.049 Uiso 1 1 calc R U . . .
H9B H -0.5702 0.5719 0.5358 0.049 Uiso 1 1 calc R U . . .
H9C H -0.4558 0.5882 0.6760 0.049 Uiso 1 1 calc R U . . .
C10 C -0.0685(3) 0.63166(9) 0.3090(2) 0.0264(4) Uani 1 1 d . . . . .
H10A H -0.0750 0.6609 0.2331 0.032 Uiso 1 1 calc R U . . .
H10B H -0.1379 0.5982 0.2765 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1153(3) 0.61317(9) 0.3420(2) 0.0254(4) Uani 1 1 d . . . . .
H11 H 0.1871 0.6483 0.3561 0.031 Uiso 1 1 calc R U . . .
C12 C 0.1830(3) 0.57721(10) 0.2245(3) 0.0320(5) Uani 1 1 d . . . . .
H12A H 0.3003 0.5660 0.2513 0.048 Uiso 1 1 calc R U . . .
H12B H 0.1791 0.5998 0.1372 0.048 Uiso 1 1 calc R U . . .
H12C H 0.1133 0.5427 0.2095 0.048 Uiso 1 1 calc R U . . .
O3 O 0.14049(18) 0.59477(6) 0.75683(16) 0.0214(3) Uani 1 1 d . . . . .
O4 O 0.13923(18) 0.50171(6) 0.69658(16) 0.0230(3) Uani 1 1 d . . . . .
O5 O -0.14026(19) 0.66494(6) 0.72589(17) 0.0240(3) Uani 1 1 d . . . . .
O6 O -0.3487(2) 0.67685(9) 0.8645(2) 0.0449(5) Uani 1 1 d . . . . .
C13 C 0.1904(3) 0.54333(9) 0.7713(2) 0.0220(4) Uani 1 1 d . . . . .
C14 C 0.3215(3) 0.53251(10) 0.8910(2) 0.0300(5) Uani 1 1 d . . . . .
H14A H 0.2659 0.5186 0.9735 0.045 Uiso 1 1 calc R U . . .
H14B H 0.3820 0.5683 0.9151 0.045 Uiso 1 1 calc R U . . .
H14C H 0.4020 0.5035 0.8623 0.045 Uiso 1 1 calc R U . . .
C15 C -0.1866(3) 0.59332(11) 0.9037(3) 0.0364(5) Uani 1 1 d . . . . .
H15A H -0.2674 0.5867 0.9755 0.055 Uiso 1 1 calc R U . . .
H15B H -0.0719 0.5961 0.9494 0.055 Uiso 1 1 calc R U . . .
H15C H -0.1919 0.5613 0.8365 0.055 Uiso 1 1 calc R U . . .
C16 C -0.2299(3) 0.64796(10) 0.8268(3) 0.0298(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 1.8904(14) . ?
Co1 O1 1.8999(14) . ?
Co1 O3 1.9152(16) . ?
Co1 O5 1.9375(15) . ?
Co1 N2 1.9380(19) . ?
Co1 N1 1.9441(17) . ?
Co2 O1 2.0718(14) 3_566 ?
Co2 O1 2.0719(14) . ?
Co2 O4 2.0980(17) . ?
Co2 O4 2.0980(17) 3_566 ?
Co2 O2 2.1620(14) 3_566 ?
Co2 O2 2.1621(14) . ?
N1 C1 1.335(3) . ?
N1 C5 1.357(3) . ?
N2 C7 1.487(3) . ?
N2 C6 1.489(3) . ?
N2 C10 1.504(3) . ?
O1 C8 1.441(3) . ?
O2 C11 1.418(3) . ?
C1 C2 1.400(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.496(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.544(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.518(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.528(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.522(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O3 C13 1.265(2) . ?
O4 C13 1.251(3) . ?
O5 C16 1.295(3) . ?
O6 C16 1.230(3) . ?
C13 C14 1.504(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.494(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O1 85.76(6) . . ?
O2 Co1 O3 91.58(6) . . ?
O1 Co1 O3 99.31(6) . . ?
O2 Co1 O5 177.00(7) . . ?
O1 Co1 O5 93.40(6) . . ?
O3 Co1 O5 91.39(7) . . ?
O2 Co1 N2 88.17(7) . . ?
O1 Co1 N2 86.09(7) . . ?
O3 Co1 N2 174.56(7) . . ?
O5 Co1 N2 88.90(7) . . ?
O2 Co1 N1 92.47(7) . . ?
O1 Co1 N1 171.21(7) . . ?
O3 Co1 N1 89.33(7) . . ?
O5 Co1 N1 87.93(7) . . ?
N2 Co1 N1 85.25(8) . . ?
O1 Co2 O1 180.0 3_566 . ?
O1 Co2 O4 93.01(6) 3_566 . ?
O1 Co2 O4 86.99(6) . . ?
O1 Co2 O4 87.00(6) 3_566 3_566 ?
O1 Co2 O4 93.00(6) . 3_566 ?
O4 Co2 O4 180.00(7) . 3_566 ?
O1 Co2 O2 75.02(5) 3_566 3_566 ?
O1 Co2 O2 104.98(5) . 3_566 ?
O4 Co2 O2 96.43(6) . 3_566 ?
O4 Co2 O2 83.57(6) 3_566 3_566 ?
O1 Co2 O2 104.98(5) 3_566 . ?
O1 Co2 O2 75.02(5) . . ?
O4 Co2 O2 83.57(6) . . ?
O4 Co2 O2 96.43(6) 3_566 . ?
O2 Co2 O2 180.00(3) 3_566 . ?
C1 N1 C5 120.07(19) . . ?
C1 N1 Co1 127.03(15) . . ?
C5 N1 Co1 112.74(16) . . ?
C7 N2 C6 112.56(17) . . ?
C7 N2 C10 112.02(18) . . ?
C6 N2 C10 112.08(17) . . ?
C7 N2 Co1 105.14(14) . . ?
C6 N2 Co1 107.12(14) . . ?
C10 N2 Co1 107.42(13) . . ?
C8 O1 Co1 112.93(12) . . ?
C8 O1 Co2 119.62(12) . . ?
Co1 O1 Co2 98.21(6) . . ?
C11 O2 Co1 108.49(11) . . ?
C11 O2 Co2 125.15(13) . . ?
Co1 O2 Co2 95.47(6) . . ?
N1 C1 C2 121.8(2) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 120.9(2) . . ?
N1 C5 C6 114.61(18) . . ?
C4 C5 C6 124.5(2) . . ?
N2 C6 C5 108.95(17) . . ?
N2 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C8 109.03(17) . . ?
N2 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
N2 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O1 C8 C9 110.25(19) . . ?
O1 C8 C7 110.29(17) . . ?
C9 C8 C7 110.80(18) . . ?
O1 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 108.50(19) . . ?
N2 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
N2 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O2 C11 C12 110.74(17) . . ?
O2 C11 C10 107.19(17) . . ?
C12 C11 C10 112.7(2) . . ?
O2 C11 H11 108.7 . . ?
C12 C11 H11 108.7 . . ?
C10 C11 H11 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 O3 Co1 124.44(14) . . ?
C13 O4 Co2 130.33(14) . . ?
C16 O5 Co1 131.21(14) . . ?
O4 C13 O3 125.8(2) . . ?
O4 C13 C14 118.46(19) . . ?
O3 C13 C14 115.72(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 O5 121.3(2) . . ?
O6 C16 C15 118.5(2) . . ?
O5 C16 C15 120.1(2) . . ?

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
O2 Co1 O1 C8 -108.13(13) . . . . ?
O3 Co1 O1 C8 160.96(13) . . . . ?
O5 Co1 O1 C8 68.99(13) . . . . ?
N2 Co1 O1 C8 -19.68(13) . . . . ?
O2 Co1 O1 Co2 18.97(6) . . . . ?
O3 Co1 O1 Co2 -71.94(7) . . . . ?
O5 Co1 O1 Co2 -163.91(7) . . . . ?
N2 Co1 O1 Co2 107.42(7) . . . . ?
O1 Co1 O2 C11 111.89(14) . . . . ?
O3 Co1 O2 C11 -148.89(13) . . . . ?
N2 Co1 O2 C11 25.67(14) . . . . ?
N1 Co1 O2 C11 -59.49(14) . . . . ?
O1 Co1 O2 Co2 -18.04(6) . . . . ?
O3 Co1 O2 Co2 81.18(6) . . . . ?
N2 Co1 O2 Co2 -104.26(7) . . . . ?
N1 Co1 O2 Co2 170.58(7) . . . . ?
C5 N1 C1 C2 -1.1(3) . . . . ?
Co1 N1 C1 C2 174.12(17) . . . . ?
N1 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 2.2(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C1 N1 C5 C4 1.9(3) . . . . ?
Co1 N1 C5 C4 -173.96(17) . . . . ?
C1 N1 C5 C6 -178.10(19) . . . . ?
Co1 N1 C5 C6 6.0(2) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
C7 N2 C6 C5 150.84(19) . . . . ?
C10 N2 C6 C5 -81.8(2) . . . . ?
Co1 N2 C6 C5 35.8(2) . . . . ?
N1 C5 C6 N2 -28.0(3) . . . . ?
C4 C5 C6 N2 152.0(2) . . . . ?
C6 N2 C7 C8 -158.51(19) . . . . ?
C10 N2 C7 C8 74.1(2) . . . . ?
Co1 N2 C7 C8 -42.2(2) . . . . ?
Co1 O1 C8 C9 -123.26(15) . . . . ?
Co2 O1 C8 C9 121.98(16) . . . . ?
Co1 O1 C8 C7 -0.6(2) . . . . ?
Co2 O1 C8 C7 -115.34(16) . . . . ?
N2 C7 C8 O1 28.7(2) . . . . ?
N2 C7 C8 C9 151.03(19) . . . . ?
C7 N2 C10 C11 -140.55(18) . . . . ?
C6 N2 C10 C11 91.8(2) . . . . ?
Co1 N2 C10 C11 -25.58(19) . . . . ?
Co1 O2 C11 C12 -168.63(15) . . . . ?
Co2 O2 C11 C12 -57.6(2) . . . . ?
Co1 O2 C11 C10 -45.35(18) . . . . ?
Co2 O2 C11 C10 65.65(19) . . . . ?
N2 C10 C11 O2 46.7(2) . . . . ?
N2 C10 C11 C12 168.76(17) . . . . ?
Co2 O4 C13 O3 14.8(3) . . . . ?
Co2 O4 C13 C14 -165.91(14) . . . . ?
Co1 O3 C13 O4 -8.8(3) . . . . ?
Co1 O3 C13 C14 171.92(13) . . . . ?
Co1 O5 C16 O6 -156.27(18) . . . . ?
Co1 O5 C16 C15 25.9(3) . . . . ?

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.113

_shelxl_version_number           2013-2
