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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1811142'
_audit_update_record             
;
2018-02-10 deposited with the CCDC.
2018-04-09 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 H32 Co3 N2 O22'
_chemical_formula_weight         925.34

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

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

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

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

_cell_length_a                   17.0967(15)
_cell_length_b                   13.6362(13)
_cell_length_c                   7.1320(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.993(4)
_cell_angle_gamma                90
_cell_volume                     1646.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9518
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.37

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_F_000             942
_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    1.594
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.883
_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      298(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            25991
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.832
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_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             2916
_reflns_number_gt                2446
_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)+(0.0469P)²+2.3967P] 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         2916
_refine_ls_number_parameters     280
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.29074(3) 0.41072(3) 0.84555(7) 0.01946(15) Uani 1 1 d . . . . .
Co2 Co 0.0000 0.5000 0.5000 0.02598(19) Uani 1 2 d S . P . .
O1 O 0.20882(15) 0.45692(18) 0.6056(4) 0.0286(6) Uani 1 1 d . . . . .
O2 O 0.11274(13) 0.55247(18) 0.4630(4) 0.0296(6) Uani 1 1 d . . . . .
O3 O 0.18713(15) 0.91287(18) 0.5041(4) 0.0371(7) Uani 1 1 d . . . . .
O4 O 0.30762(13) 0.95035(17) 0.4424(3) 0.0236(5) Uani 1 1 d . . . . .
O5 O 0.71499(13) 0.72313(18) 0.2976(4) 0.0272(6) Uani 1 1 d . . . . .
O6 O 0.64064(14) 0.83477(17) 0.4187(4) 0.0275(6) Uani 1 1 d . . . . .
O7 O 0.18764(17) 0.3956(2) 0.9767(4) 0.0326(7) Uani 1 1 d . . . . .
H7B H 0.184(3) 0.445(4) 0.998(7) 0.049 Uiso 1 1 d . U . . .
H7A H 0.186(3) 0.365(4) 1.074(7) 0.049 Uiso 1 1 d . U . . .
O8 O -0.04068(19) 0.5675(3) 0.2547(5) 0.0715(12) Uani 1 1 d D . . . .
H8C H -0.012(3) 0.592(5) 0.180(7) 0.107 Uiso 1 1 d D U . . .
H8A H -0.0885(13) 0.576(5) 0.209(8) 0.107 Uiso 1 1 d D U . . .
O9 O 0.00856(19) 0.3624(2) 0.3548(5) 0.0531(9) Uani 1 1 d D . . . .
H9A H 0.0594(13) 0.351(4) 0.358(8) 0.080 Uiso 1 1 d D U . . .
H9B H -0.010(3) 0.307(2) 0.387(8) 0.080 Uiso 1 1 d D U . . .
O10 O 1.1577(2) 0.3207(3) 0.3348(5) 0.0515(9) Uani 1 1 d . . . . .
H10B H 1.178(3) 0.361(4) 0.434(8) 0.077 Uiso 1 1 d . U . . .
H10C H 1.184(3) 0.268(5) 0.329(8) 0.077 Uiso 1 1 d . U . . .
O11 O 1.04433(18) 0.8282(2) 0.5360(5) 0.0496(8) Uani 1 1 d D . . . .
H11A H 1.085(2) 0.861(4) 0.565(7) 0.074 Uiso 1 1 d D U . . .
H11B H 1.022(3) 0.839(4) 0.424(4) 0.074 Uiso 1 1 d D U . . .
N1 N 0.59934(15) 0.59213(19) 0.2593(4) 0.0171(6) Uani 1 1 d . . . . .
C1 C 0.18349(19) 0.5344(2) 0.5210(5) 0.0204(7) Uani 1 1 d . . . . .
C2 C 0.24267(19) 0.6122(2) 0.4866(5) 0.0182(7) Uani 1 1 d . . . . .
C3 C 0.22116(18) 0.7103(2) 0.4906(5) 0.0186(7) Uani 1 1 d . . . . .
H3A H 0.1704 0.7273 0.5114 0.022 Uiso 1 1 calc R U . . .
C4 C 0.27537(19) 0.7833(2) 0.4637(5) 0.0169(7) Uani 1 1 d . . . . .
C5 C 0.34943(18) 0.7567(2) 0.4249(4) 0.0167(7) Uani 1 1 d . . . . .
H5A H 0.3855 0.8055 0.4058 0.020 Uiso 1 1 calc R U . . .
C6 C 0.37157(18) 0.6592(2) 0.4134(4) 0.0164(7) Uani 1 1 d . . . . .
C7 C 0.31725(18) 0.5870(2) 0.4473(5) 0.0179(7) Uani 1 1 d . . . . .
H7C H 0.3313 0.5212 0.4436 0.022 Uiso 1 1 calc R U . . .
C8 C 0.25453(19) 0.8900(2) 0.4710(5) 0.0201(7) Uani 1 1 d . . . . .
C9 C 0.45043(18) 0.6343(2) 0.3622(4) 0.0166(7) Uani 1 1 d . . . . .
C10 C 0.46585(19) 0.5450(2) 0.2789(5) 0.0192(7) Uani 1 1 d . . . . .
H10A H 0.4263 0.4980 0.2545 0.023 Uiso 1 1 calc R U . . .
C11 C 0.54056(19) 0.5271(2) 0.2329(5) 0.0194(7) Uani 1 1 d . . . . .
H11C H 0.5503 0.4665 0.1808 0.023 Uiso 1 1 calc R U . . .
C12 C 0.58428(18) 0.6794(2) 0.3346(4) 0.0168(7) Uani 1 1 d . . . . .
C13 C 0.51259(18) 0.7018(2) 0.3904(4) 0.0181(7) Uani 1 1 d . . . . .
H13A H 0.5054 0.7619 0.4471 0.022 Uiso 1 1 calc R U . . .
C14 C 0.65199(19) 0.7528(2) 0.3526(5) 0.0197(7) 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 O4 2.023(2) 4_576 ?
Co1 O5 2.087(2) 3_666 ?
Co1 O7 2.117(3) . ?
Co1 N1 2.117(3) 3_666 ?
Co1 O1 2.149(2) . ?
Co1 O6 2.174(2) 2_646 ?
Co2 O8 2.013(3) . ?
Co2 O8 2.013(3) 3_566 ?
Co2 O2 2.107(2) 3_566 ?
Co2 O2 2.107(2) . ?
Co2 O9 2.158(3) 3_566 ?
Co2 O9 2.158(3) . ?
O1 C1 1.263(4) . ?
O2 C1 1.247(4) . ?
O3 C8 1.248(4) . ?
O4 C8 1.263(4) . ?
O4 Co1 2.023(2) 4_575 ?
O5 C14 1.263(4) . ?
O5 Co1 2.087(2) 3_666 ?
O6 C14 1.239(4) . ?
O6 Co1 2.174(2) 2_656 ?
O7 H7B 0.70(5) . ?
O7 H7A 0.82(5) . ?
O8 H8C 0.85(2) . ?
O8 H8A 0.85(2) . ?
O9 H9A 0.880(19) . ?
O9 H9B 0.869(19) . ?
O10 H10B 0.92(6) . ?
O10 H10C 0.85(6) . ?
O11 H11A 0.833(19) . ?
O11 H11B 0.845(19) . ?
N1 C11 1.334(4) . ?
N1 C12 1.346(4) . ?
N1 Co1 2.117(3) 3_666 ?
C1 C2 1.509(4) . ?
C2 C7 1.386(5) . ?
C2 C3 1.389(5) . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(4) . ?
C4 C8 1.500(4) . ?
C5 C6 1.388(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.397(4) . ?
C6 C9 1.484(4) . ?
C7 H7C 0.9300 . ?
C9 C10 1.397(5) . ?
C9 C13 1.399(5) . ?
C10 C11 1.384(4) . ?
C10 H10A 0.9300 . ?
C11 H11C 0.9300 . ?
C12 C13 1.374(4) . ?
C12 C14 1.522(4) . ?
C13 H13A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 O5 168.70(10) 4_576 3_666 ?
O4 Co1 O7 91.62(10) 4_576 . ?
O5 Co1 O7 98.37(10) 3_666 . ?
O4 Co1 N1 92.65(10) 4_576 3_666 ?
O5 Co1 N1 78.16(10) 3_666 3_666 ?
O7 Co1 N1 171.32(11) . 3_666 ?
O4 Co1 O1 92.49(10) 4_576 . ?
O5 Co1 O1 83.45(10) 3_666 . ?
O7 Co1 O1 83.67(11) . . ?
N1 Co1 O1 103.67(10) 3_666 . ?
O4 Co1 O6 98.39(10) 4_576 2_646 ?
O5 Co1 O6 86.87(10) 3_666 2_646 ?
O7 Co1 O6 90.28(11) . 2_646 ?
N1 Co1 O6 81.63(10) 3_666 2_646 ?
O1 Co1 O6 167.70(9) . 2_646 ?
O8 Co2 O8 180.0 . 3_566 ?
O8 Co2 O2 93.02(12) . 3_566 ?
O8 Co2 O2 86.98(12) 3_566 3_566 ?
O8 Co2 O2 86.98(12) . . ?
O8 Co2 O2 93.02(12) 3_566 . ?
O2 Co2 O2 180.0 3_566 . ?
O8 Co2 O9 88.90(18) . 3_566 ?
O8 Co2 O9 91.10(18) 3_566 3_566 ?
O2 Co2 O9 96.37(11) 3_566 3_566 ?
O2 Co2 O9 83.64(11) . 3_566 ?
O8 Co2 O9 91.10(18) . . ?
O8 Co2 O9 88.90(18) 3_566 . ?
O2 Co2 O9 83.63(11) 3_566 . ?
O2 Co2 O9 96.37(11) . . ?
O9 Co2 O9 180.0 3_566 . ?
C1 O1 Co1 140.1(2) . . ?
C1 O2 Co2 138.9(2) . . ?
C8 O4 Co1 126.4(2) . 4_575 ?
C14 O5 Co1 116.6(2) . 3_666 ?
C14 O6 Co1 128.9(2) . 2_656 ?
Co1 O7 H7B 97(4) . . ?
Co1 O7 H7A 124(3) . . ?
H7B O7 H7A 107(6) . . ?
Co2 O8 H8C 124(4) . . ?
Co2 O8 H8A 127(4) . . ?
H8C O8 H8A 109(3) . . ?
Co2 O9 H9A 106(4) . . ?
Co2 O9 H9B 125(4) . . ?
H9A O9 H9B 103(3) . . ?
H10B O10 H10C 113(5) . . ?
H11A O11 H11B 114(3) . . ?
C11 N1 C12 117.5(3) . . ?
C11 N1 Co1 128.8(2) . 3_666 ?
C12 N1 Co1 112.7(2) . 3_666 ?
O2 C1 O1 125.1(3) . . ?
O2 C1 C2 116.7(3) . . ?
O1 C1 C2 118.2(3) . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 C8 119.4(3) . . ?
C3 C4 C8 121.5(3) . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 C9 119.8(3) . . ?
C7 C6 C9 122.1(3) . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 H7C 119.6 . . ?
C6 C7 H7C 119.6 . . ?
O3 C8 O4 124.8(3) . . ?
O3 C8 C4 118.6(3) . . ?
O4 C8 C4 116.6(3) . . ?
C10 C9 C13 116.8(3) . . ?
C10 C9 C6 122.4(3) . . ?
C13 C9 C6 120.8(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
N1 C11 C10 123.5(3) . . ?
N1 C11 H11C 118.3 . . ?
C10 C11 H11C 118.3 . . ?
N1 C12 C13 122.7(3) . . ?
N1 C12 C14 115.4(3) . . ?
C13 C12 C14 121.9(3) . . ?
C12 C13 C9 120.2(3) . . ?
C12 C13 H13A 119.9 . . ?
C9 C13 H13A 119.9 . . ?
O6 C14 O5 126.3(3) . . ?
O6 C14 C12 117.9(3) . . ?
O5 C14 C12 115.8(3) . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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 1811143'
_audit_update_record             
;
2018-02-10 deposited with the CCDC.
2018-04-09 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 H32 N2 Ni3 O22'
_chemical_formula_weight         924.68

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'
Ni Ni 0.3393 1.1124 '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                   16.6233(15)
_cell_length_b                   13.4654(13)
_cell_length_c                   7.1298(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.442(4)
_cell_angle_gamma                90
_cell_volume                     1569.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9023
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_F_000             948
_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    1.887
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.864
_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      298(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            22393
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.915
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_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             2768
_reflns_number_gt                2162
_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)+(0.0531P)²+4.4074P] 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         2768
_refine_ls_number_parameters     268
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.045
_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
Ni1 Ni 1.71648(3) 0.59554(4) 0.17591(8) 0.01963(18) Uani 1 1 d . . . . .
Ni2 Ni 2.0000 0.5000 0.5000 0.0377(3) Uani 1 2 d S . P . .
O1 O 1.79501(19) 0.5471(2) 0.4255(5) 0.0312(8) Uani 1 1 d . . . . .
O2 O 1.89358(19) 0.4403(3) 0.5402(6) 0.0452(10) Uani 1 1 d . . . . .
O3 O 1.8227(2) 0.0825(2) 0.5230(6) 0.0362(9) Uani 1 1 d . . . . .
O4 O 1.69884(18) 0.0434(2) 0.5763(5) 0.0237(7) Uani 1 1 d . . . . .
O5 O 1.27663(18) 0.2662(2) 0.6980(5) 0.0267(7) Uani 1 1 d . . . . .
O6 O 1.35324(19) 0.1568(2) 0.5738(5) 0.0274(7) Uani 1 1 d . . . . .
O7 O 1.8190(2) 0.6186(3) 0.0544(6) 0.0363(9) Uani 1 1 d D . . . .
H7A H 1.823(3) 0.564(3) 0.001(7) 0.054 Uiso 1 1 d D U . . .
H7C H 1.857(3) 0.628(4) 0.146(6) 0.054 Uiso 1 1 d D U . . .
O8 O 1.9784(3) 0.4543(5) 0.2178(9) 0.0849(17) Uani 1 1 d D . . . .
H8A H 1.930(3) 0.431(6) 0.179(14) 0.127 Uiso 1 1 d D U . . .
H8C H 1.973(5) 0.5182(16) 0.216(16) 0.127 Uiso 1 1 d D U . . .
O9 O 2.0519(3) 0.3642(3) 0.5775(10) 0.0784(18) Uani 1 1 d D . . . .
H9A H 2.1027(15) 0.352(6) 0.591(14) 0.118 Uiso 1 1 d D U . . .
H9B H 2.026(4) 0.311(4) 0.588(13) 0.118 Uiso 1 1 d D U . . .
O10 O 1.1311(12) 0.3264(13) 0.277(3) 0.368(11) Uani 1 1 d . . . . .
O11 O 1.0229(5) 0.8127(5) 0.6009(11) 0.124(3) Uani 1 1 d . . . . .
N1 N 1.3939(2) 0.4030(2) 0.7322(5) 0.0176(7) Uani 1 1 d . . . . .
C1 C 1.8201(3) 0.4641(3) 0.4944(7) 0.0253(10) Uani 1 1 d . . . . .
C2 C 1.7604(2) 0.3852(3) 0.5271(6) 0.0192(9) Uani 1 1 d . . . . .
C3 C 1.7831(2) 0.2865(3) 0.5233(6) 0.0191(9) Uani 1 1 d . . . . .
H3A H 1.8351 0.2699 0.5023 0.023 Uiso 1 1 calc R U . . .
C4 C 1.7288(2) 0.2123(3) 0.5508(6) 0.0161(9) Uani 1 1 d . . . . .
C5 C 1.6527(2) 0.2381(3) 0.5864(6) 0.0158(9) Uani 1 1 d . . . . .
H5A H 1.6162 0.1882 0.6049 0.019 Uiso 1 1 calc R U . . .
C6 C 1.6291(2) 0.3364(3) 0.5954(6) 0.0161(9) Uani 1 1 d . . . . .
C7 C 1.6837(3) 0.4104(3) 0.5639(6) 0.0202(9) Uani 1 1 d . . . . .
H7B H 1.6688 0.4768 0.5676 0.024 Uiso 1 1 calc R U . . .
C8 C 1.7527(3) 0.1044(3) 0.5491(6) 0.0189(9) Uani 1 1 d . . . . .
C9 C 1.5480(3) 0.3610(3) 0.6430(6) 0.0173(9) Uani 1 1 d . . . . .
C10 C 1.5315(3) 0.4510(3) 0.7226(6) 0.0199(9) Uani 1 1 d . . . . .
H10A H 1.5722 0.4991 0.7483 0.024 Uiso 1 1 calc R U . . .
C11 C 1.4544(3) 0.4693(3) 0.7641(6) 0.0208(9) Uani 1 1 d . . . . .
H11A H 1.4446 0.5304 0.8163 0.025 Uiso 1 1 calc R U . . .
C12 C 1.4097(2) 0.3148(3) 0.6609(6) 0.0181(9) Uani 1 1 d . . . . .
C13 C 1.4841(2) 0.2922(3) 0.6116(6) 0.0179(9) Uani 1 1 d . . . . .
H13A H 1.4918 0.2310 0.5573 0.021 Uiso 1 1 calc R U . . .
C14 C 1.3412(3) 0.2392(3) 0.6408(6) 0.0209(10) 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 O4 2.004(3) 4_565 ?
Ni1 N1 2.056(3) 3_866 ?
Ni1 O5 2.061(3) 3_866 ?
Ni1 O7 2.071(3) . ?
Ni1 O6 2.108(3) 2_855 ?
Ni1 O1 2.111(3) . ?
Ni2 O2 2.010(3) 3_966 ?
Ni2 O2 2.010(3) . ?
Ni2 O9 2.055(4) . ?
Ni2 O9 2.055(4) 3_966 ?
Ni2 O8 2.072(6) 3_966 ?
Ni2 O8 2.072(6) . ?
Ni2 H8C 2.01(11) . ?
O1 C1 1.260(5) . ?
O2 C1 1.248(6) . ?
O3 C8 1.247(5) . ?
O4 C8 1.256(5) . ?
O4 Ni1 2.003(3) 4_566 ?
O5 C14 1.269(5) . ?
O5 Ni1 2.061(3) 3_866 ?
O6 C14 1.239(5) . ?
O6 Ni1 2.108(3) 2_845 ?
O7 H7A 0.838(19) . ?
O7 H7C 0.835(19) . ?
O8 H8A 0.86(2) . ?
O8 H8C 0.86(2) . ?
O9 H9A 0.85(2) . ?
O9 H9B 0.85(2) . ?
N1 C11 1.334(5) . ?
N1 C12 1.337(5) . ?
N1 Ni1 2.056(3) 3_866 ?
C1 C2 1.500(6) . ?
C2 C3 1.384(6) . ?
C2 C7 1.389(6) . ?
C3 C4 1.384(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(6) . ?
C4 C8 1.507(6) . ?
C5 C6 1.386(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.392(6) . ?
C6 C9 1.487(6) . ?
C7 H7B 0.9300 . ?
C9 C10 1.386(6) . ?
C9 C13 1.396(6) . ?
C10 C11 1.389(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(6) . ?
C12 C14 1.513(6) . ?
C13 H13A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ni1 N1 92.31(13) 4_565 3_866 ?
O4 Ni1 O5 172.19(12) 4_565 3_866 ?
N1 Ni1 O5 80.48(12) 3_866 3_866 ?
O4 Ni1 O7 94.02(13) 4_565 . ?
N1 Ni1 O7 168.86(14) 3_866 . ?
O5 Ni1 O7 93.58(13) 3_866 . ?
O4 Ni1 O6 92.48(12) 4_565 2_855 ?
N1 Ni1 O6 83.08(13) 3_866 2_855 ?
O5 Ni1 O6 89.63(13) 3_866 2_855 ?
O7 Ni1 O6 87.49(14) . 2_855 ?
O4 Ni1 O1 92.20(12) 4_565 . ?
N1 Ni1 O1 100.69(13) 3_866 . ?
O5 Ni1 O1 86.25(13) 3_866 . ?
O7 Ni1 O1 88.22(14) . . ?
O6 Ni1 O1 173.86(12) 2_855 . ?
O2 Ni2 O2 180.0 3_966 . ?
O2 Ni2 O9 93.28(17) 3_966 . ?
O2 Ni2 O9 86.72(16) . . ?
O2 Ni2 O9 86.72(16) 3_966 3_966 ?
O2 Ni2 O9 93.28(17) . 3_966 ?
O9 Ni2 O9 180.0 . 3_966 ?
O2 Ni2 O8 91.0(2) 3_966 3_966 ?
O2 Ni2 O8 89.0(2) . 3_966 ?
O9 Ni2 O8 90.7(3) . 3_966 ?
O9 Ni2 O8 89.3(3) 3_966 3_966 ?
O2 Ni2 O8 89.0(2) 3_966 . ?
O2 Ni2 O8 91.0(2) . . ?
O9 Ni2 O8 89.3(3) . . ?
O9 Ni2 O8 90.7(3) 3_966 . ?
O8 Ni2 O8 180.0 3_966 . ?
O2 Ni2 H8C 81(2) 3_966 . ?
O2 Ni2 H8C 99(2) . . ?
O9 Ni2 H8C 112.6(12) . . ?
O9 Ni2 H8C 67.4(12) 3_966 . ?
O8 Ni2 H8C 155.6(7) 3_966 . ?
O8 Ni2 H8C 24.4(7) . . ?
C1 O1 Ni1 135.5(3) . . ?
C1 O2 Ni2 134.8(3) . . ?
C8 O4 Ni1 127.1(3) . 4_566 ?
C14 O5 Ni1 114.5(3) . 3_866 ?
C14 O6 Ni1 125.0(3) . 2_845 ?
Ni1 O7 H7A 102(4) . . ?
Ni1 O7 H7C 105(4) . . ?
H7A O7 H7C 112(3) . . ?
Ni2 O8 H8A 114(7) . . ?
Ni2 O8 H8C 74(7) . . ?
H8A O8 H8C 107(3) . . ?
Ni2 O9 H9A 125(5) . . ?
Ni2 O9 H9B 126(5) . . ?
H9A O9 H9B 109(3) . . ?
C11 N1 C12 117.7(4) . . ?
C11 N1 Ni1 128.9(3) . 3_866 ?
C12 N1 Ni1 112.2(3) . 3_866 ?
O2 C1 O1 124.7(4) . . ?
O2 C1 C2 114.9(4) . . ?
O1 C1 C2 120.4(4) . . ?
C3 C2 C7 120.0(4) . . ?
C3 C2 C1 119.2(4) . . ?
C7 C2 C1 120.8(4) . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 C8 119.8(4) . . ?
C3 C4 C8 121.0(4) . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C7 118.6(4) . . ?
C5 C6 C9 119.9(4) . . ?
C7 C6 C9 121.5(4) . . ?
C2 C7 C6 120.2(4) . . ?
C2 C7 H7B 119.9 . . ?
C6 C7 H7B 119.9 . . ?
O3 C8 O4 125.4(4) . . ?
O3 C8 C4 119.0(4) . . ?
O4 C8 C4 115.7(4) . . ?
C10 C9 C13 116.4(4) . . ?
C10 C9 C6 122.8(4) . . ?
C13 C9 C6 120.7(4) . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
N1 C11 C10 122.9(4) . . ?
N1 C11 H11A 118.6 . . ?
C10 C11 H11A 118.6 . . ?
N1 C12 C13 122.6(4) . . ?
N1 C12 C14 115.9(4) . . ?
C13 C12 C14 121.4(4) . . ?
C12 C13 C9 120.3(4) . . ?
C12 C13 H13A 119.9 . . ?
C9 C13 H13A 119.9 . . ?
O6 C14 O5 125.8(4) . . ?
O6 C14 C12 117.9(4) . . ?
O5 C14 C12 116.3(4) . . ?

_refine_diff_density_max         0.869
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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 1811144'
_audit_update_record             
;
2018-02-10 deposited with the CCDC.
2018-04-09 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 H32 N2 Ni3 O22'
_chemical_formula_weight         924.68

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'
Ni Ni 0.3393 1.1124 '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                   16.699(4)
_cell_length_b                   13.510(3)
_cell_length_c                   7.1625(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.626(9)
_cell_angle_gamma                90
_cell_volume                     1588.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5958
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.60

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_F_000             948
_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    1.865
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            25103
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_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                2185
_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)+(0.0595P)²+3.5561P] 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     268
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_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 1.71595(3) 0.59498(4) 0.17827(8) 0.01955(19) Uani 1 1 d . . . . .
Ni2 Ni 2.0000 0.5000 0.5000 0.0381(3) Uani 1 2 d S . P . .
O1 O 1.79508(19) 0.5461(2) 0.4270(5) 0.0291(8) Uani 1 1 d . . . . .
O2 O 1.8938(2) 0.4401(3) 0.5417(6) 0.0443(10) Uani 1 1 d . . . . .
O3 O 1.8221(2) 0.0819(2) 0.5242(6) 0.0349(9) Uani 1 1 d . . . . .
O4 O 1.69869(17) 0.0437(2) 0.5772(5) 0.0228(7) Uani 1 1 d . . . . .
O5 O 1.27799(18) 0.2673(2) 0.6930(5) 0.0276(8) Uani 1 1 d . . . . .
O6 O 1.35445(18) 0.1581(2) 0.5713(5) 0.0258(7) Uani 1 1 d . . . . .
O7 O 1.8182(2) 0.6197(3) 0.0531(6) 0.0375(9) Uani 1 1 d D . . . .
H7A H 1.823(4) 0.562(2) 0.015(7) 0.056 Uiso 1 1 d D U . . .
H7C H 1.847(3) 0.632(4) 0.156(5) 0.056 Uiso 1 1 d D U . . .
O8 O 1.9770(3) 0.4543(5) 0.2177(10) 0.0865(17) Uani 1 1 d D . . . .
H8A H 1.932(3) 0.427(5) 0.185(15) 0.130 Uiso 1 1 d D U . . .
H8C H 1.973(5) 0.5158(9) 0.212(16) 0.130 Uiso 1 1 d D U . . .
O9 O 2.0533(3) 0.3641(3) 0.5775(9) 0.0752(16) Uani 1 1 d D . . . .
H9A H 2.040(6) 0.349(6) 0.463(3) 0.113 Uiso 1 1 d D U . . .
H9B H 2.035(5) 0.325(5) 0.649(8) 0.113 Uiso 1 1 d D U . . .
O10 O 1.1342(13) 0.3288(13) 0.276(4) 0.430(14) Uani 1 1 d . . . . .
O11 O 1.0215(5) 0.8132(5) 0.5993(10) 0.122(2) Uani 1 1 d . . . . .
N1 N 1.3951(2) 0.4033(2) 0.7308(5) 0.0153(7) Uani 1 1 d . . . . .
C1 C 1.8203(3) 0.4639(3) 0.4967(7) 0.0254(11) Uani 1 1 d . . . . .
C2 C 1.7610(3) 0.3846(3) 0.5291(6) 0.0192(9) Uani 1 1 d . . . . .
C3 C 1.7837(2) 0.2868(3) 0.5262(6) 0.0174(9) Uani 1 1 d . . . . .
H3A H 1.8356 0.2704 0.5069 0.021 Uiso 1 1 calc R U . . .
C4 C 1.7289(2) 0.2118(3) 0.5522(6) 0.0153(9) Uani 1 1 d . . . . .
C5 C 1.6530(2) 0.2379(3) 0.5872(6) 0.0151(9) Uani 1 1 d . . . . .
H5A H 1.6165 0.1883 0.6049 0.018 Uiso 1 1 calc R U . . .
C6 C 1.6298(2) 0.3364(3) 0.5967(6) 0.0145(9) Uani 1 1 d . . . . .
C7 C 1.6844(2) 0.4099(3) 0.5651(6) 0.0172(9) Uani 1 1 d . . . . .
H7B H 1.6696 0.4761 0.5679 0.021 Uiso 1 1 calc R U . . .
C8 C 1.7527(3) 0.1045(3) 0.5504(6) 0.0183(9) Uani 1 1 d . . . . .
C9 C 1.5491(2) 0.3611(3) 0.6425(6) 0.0138(8) Uani 1 1 d . . . . .
C10 C 1.5324(2) 0.4509(3) 0.7229(6) 0.0183(9) Uani 1 1 d . . . . .
H10A H 1.5731 0.4985 0.7507 0.022 Uiso 1 1 calc R U . . .
C11 C 1.4558(3) 0.4694(3) 0.7616(6) 0.0199(9) Uani 1 1 d . . . . .
H11A H 1.4459 0.5308 0.8116 0.024 Uiso 1 1 calc R U . . .
C12 C 1.4110(2) 0.3150(3) 0.6594(6) 0.0162(9) Uani 1 1 d . . . . .
C13 C 1.4850(2) 0.2924(3) 0.6108(6) 0.0182(9) Uani 1 1 d . . . . .
H13A H 1.4925 0.2314 0.5567 0.022 Uiso 1 1 calc R U . . .
C14 C 1.3423(3) 0.2403(3) 0.6378(6) 0.0194(9) 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 O4 2.010(3) 4_565 ?
Ni1 O5 2.071(3) 3_866 ?
Ni1 N1 2.077(3) 3_866 ?
Ni1 O7 2.097(4) . ?
Ni1 O1 2.119(3) . ?
Ni1 O6 2.128(3) 2_855 ?
Ni2 O2 2.021(3) . ?
Ni2 O2 2.021(3) 3_966 ?
Ni2 O9 2.071(5) 3_966 ?
Ni2 O9 2.071(5) . ?
Ni2 O8 2.081(7) . ?
Ni2 O8 2.081(7) 3_966 ?
Ni2 H8C 2.04(11) . ?
O1 C1 1.257(5) . ?
O2 C1 1.252(6) . ?
O3 C8 1.247(5) . ?
O4 C8 1.260(5) . ?
O4 Ni1 2.010(3) 4_566 ?
O5 C14 1.264(5) . ?
O5 Ni1 2.071(3) 3_866 ?
O6 C14 1.240(5) . ?
O6 Ni1 2.128(3) 2_845 ?
O7 H7A 0.839(19) . ?
O7 H7C 0.818(19) . ?
O8 H8A 0.833(10) . ?
O8 H8C 0.834(10) . ?
O9 H9A 0.833(10) . ?
O9 H9B 0.831(10) . ?
N1 C11 1.337(5) . ?
N1 C12 1.343(5) . ?
N1 Ni1 2.077(3) 3_866 ?
C1 C2 1.506(6) . ?
C2 C3 1.375(6) . ?
C2 C7 1.393(6) . ?
C3 C4 1.400(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(6) . ?
C4 C8 1.503(6) . ?
C5 C6 1.391(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(6) . ?
C6 C9 1.483(6) . ?
C7 H7B 0.9300 . ?
C9 C10 1.392(6) . ?
C9 C13 1.403(6) . ?
C10 C11 1.382(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(6) . ?
C12 C14 1.516(6) . ?
C13 H13A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ni1 O5 171.84(12) 4_565 3_866 ?
O4 Ni1 N1 92.66(13) 4_565 3_866 ?
O5 Ni1 N1 79.83(12) 3_866 3_866 ?
O4 Ni1 O7 93.90(13) 4_565 . ?
O5 Ni1 O7 94.06(14) 3_866 . ?
N1 Ni1 O7 167.85(14) 3_866 . ?
O4 Ni1 O1 92.18(13) 4_565 . ?
O5 Ni1 O1 86.22(13) 3_866 . ?
N1 Ni1 O1 101.21(13) 3_866 . ?
O7 Ni1 O1 88.76(14) . . ?
O4 Ni1 O6 92.90(13) 4_565 2_855 ?
O5 Ni1 O6 89.31(13) 3_866 2_855 ?
N1 Ni1 O6 82.64(13) 3_866 2_855 ?
O7 Ni1 O6 86.82(14) . 2_855 ?
O1 Ni1 O6 173.47(12) . 2_855 ?
O2 Ni2 O2 180.0 . 3_966 ?
O2 Ni2 O9 92.83(17) . 3_966 ?
O2 Ni2 O9 87.17(17) 3_966 3_966 ?
O2 Ni2 O9 87.17(17) . . ?
O2 Ni2 O9 92.83(17) 3_966 . ?
O9 Ni2 O9 180.0(3) 3_966 . ?
O2 Ni2 O8 90.9(2) . . ?
O2 Ni2 O8 89.1(2) 3_966 . ?
O9 Ni2 O8 90.6(3) 3_966 . ?
O9 Ni2 O8 89.4(3) . . ?
O2 Ni2 O8 89.1(2) . 3_966 ?
O2 Ni2 O8 90.9(2) 3_966 3_966 ?
O9 Ni2 O8 89.4(3) 3_966 3_966 ?
O9 Ni2 O8 90.6(3) . 3_966 ?
O8 Ni2 O8 180.0 . 3_966 ?
O2 Ni2 H8C 99(2) . . ?
O2 Ni2 H8C 81(2) 3_966 . ?
O9 Ni2 H8C 68.4(11) 3_966 . ?
O9 Ni2 H8C 111.6(11) . . ?
O8 Ni2 H8C 23.3(5) . . ?
O8 Ni2 H8C 156.7(6) 3_966 . ?
C1 O1 Ni1 136.1(3) . . ?
C1 O2 Ni2 134.8(3) . . ?
C8 O4 Ni1 127.1(3) . 4_566 ?
C14 O5 Ni1 115.1(3) . 3_866 ?
C14 O6 Ni1 125.2(3) . 2_845 ?
Ni1 O7 H7A 97(4) . . ?
Ni1 O7 H7C 92(5) . . ?
H7A O7 H7C 115(3) . . ?
Ni2 O8 H8A 114(8) . . ?
Ni2 O8 H8C 75(8) . . ?
H8A O8 H8C 111.5(19) . . ?
Ni2 O9 H9A 86(7) . . ?
Ni2 O9 H9B 123(7) . . ?
H9A O9 H9B 112(2) . . ?
C11 N1 C12 117.3(3) . . ?
C11 N1 Ni1 129.3(3) . 3_866 ?
C12 N1 Ni1 112.3(3) . 3_866 ?
O2 C1 O1 124.7(4) . . ?
O2 C1 C2 114.7(4) . . ?
O1 C1 C2 120.6(4) . . ?
C3 C2 C7 120.2(4) . . ?
C3 C2 C1 119.4(4) . . ?
C7 C2 C1 120.4(4) . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 C8 120.0(4) . . ?
C3 C4 C8 121.1(4) . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C7 118.5(4) . . ?
C5 C6 C9 119.9(4) . . ?
C7 C6 C9 121.6(4) . . ?
C2 C7 C6 120.4(4) . . ?
C2 C7 H7B 119.8 . . ?
C6 C7 H7B 119.8 . . ?
O3 C8 O4 125.0(4) . . ?
O3 C8 C4 119.5(4) . . ?
O4 C8 C4 115.5(4) . . ?
C10 C9 C13 116.0(4) . . ?
C10 C9 C6 123.2(4) . . ?
C13 C9 C6 120.8(4) . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
N1 C11 C10 123.2(4) . . ?
N1 C11 H11A 118.4 . . ?
C10 C11 H11A 118.4 . . ?
N1 C12 C13 122.8(4) . . ?
N1 C12 C14 115.5(3) . . ?
C13 C12 C14 121.7(4) . . ?
C12 C13 C9 120.3(4) . . ?
C12 C13 H13A 119.8 . . ?
C9 C13 H13A 119.8 . . ?
O6 C14 O5 126.0(4) . . ?
O6 C14 C12 117.4(4) . . ?
O5 C14 C12 116.6(4) . . ?

_refine_diff_density_max         0.996
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.103

