# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1061092'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H88 N16 Ni2 O21'
_chemical_formula_weight         1558.94

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmc2(1)

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

_cell_length_a                   24.345(4)
_cell_length_b                   20.477(3)
_cell_length_c                   19.098(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9521(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    14385
_cell_measurement_theta_min      2.2571
_cell_measurement_theta_max      27.4971

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3224
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29797
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.50
_reflns_number_total             10913
_reflns_number_gt                10424
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         10913
_refine_ls_number_parameters     321
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.319 -0.038 0.022 6116 1279 ' '
_platon_squeeze_details          
;
The contribution of disordered solvent molecules was treated as diffuse 
using the SQUEEZE procedure implemented in PLATON, 
subsequently a set of solvent-free diffraction intensities was produced. 
The final formula of 1 was figured out based on 
the SQUEEZE results, elemental analysis data and TGA data.
;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.070287(5) -0.225397(6) 0.890813(13) 0.01423(5) Uani 1 1 d . . .
O1 O 0.0000 -0.17919(5) 0.87457(5) 0.0058(2) Uani 1 2 d S . .
O2 O 0.04608(4) -0.25397(5) 0.98895(5) 0.0247(2) Uani 1 1 d . . .
O3 O -0.04590(4) -0.68859(4) 1.34688(5) 0.0238(2) Uani 1 1 d . . .
N1 N 0.09474(5) -0.19690(6) 0.79036(6) 0.0211(2) Uani 1 1 d . . .
N2 N 0.35569(5) -0.22647(5) 0.42106(7) 0.0240(3) Uani 1 1 d . . .
N3 N 0.10135(4) 0.13650(5) 0.42989(6) 0.0195(2) Uani 1 1 d . . .
N4 N 0.13486(6) -0.06592(6) 0.57308(7) 0.0335(3) Uani 1 1 d . . .
N5 N 0.19718(6) -0.15483(7) 0.56819(7) 0.0350(3) Uani 1 1 d . . .
N6 N 0.20256(5) -0.07081(6) 0.48266(7) 0.0304(3) Uani 1 1 d . . .
C1 C 0.0000 -0.27385(8) 1.00863(10) 0.0178(4) Uani 1 2 d S . .
C2 C 0.0000 -0.32865(10) 1.06171(12) 0.0306(5) Uani 1 2 d S . .
C3 C 0.04819(8) -0.35527(11) 1.08497(14) 0.0610(7) Uani 1 1 d . . .
H3B H 0.0815 -0.3380 1.0698 0.073 Uiso 1 1 calc R . .
C4 C 0.04796(8) -0.40778(13) 1.13100(15) 0.0751(9) Uani 1 1 d . . .
H4B H 0.0812 -0.4260 1.1450 0.090 Uiso 1 1 calc R . .
C5 C 0.0000 -0.43316(13) 1.15623(17) 0.0486(7) Uani 1 2 d S . .
C6 C 0.0000 -0.49395(14) 1.20046(17) 0.0495(7) Uani 1 2 d S . .
C7A C 0.04612(16) -0.5116(2) 1.2379(2) 0.0403(11) Uiso 0.482(7) 1 d P A 1
H7AA H 0.0773 -0.4855 1.2356 0.048 Uiso 0.482(7) 1 calc PR A 1
C8A C 0.04683(17) -0.5682(2) 1.2795(2) 0.0398(11) Uiso 0.482(7) 1 d P A 1
H8AA H 0.0790 -0.5806 1.3021 0.048 Uiso 0.482(7) 1 calc PR A 1
C7B C 0.04751(15) -0.53238(19) 1.2085(2) 0.0369(10) Uiso 0.518(7) 1 d P A -2
H7BA H 0.0797 -0.5201 1.1858 0.044 Uiso 0.518(7) 1 calc PR A -2
C8B C 0.04740(15) -0.58728(19) 1.2488(2) 0.0378(10) Uiso 0.518(7) 1 d P A -2
H8BA H 0.0788 -0.6130 1.2514 0.045 Uiso 0.518(7) 1 calc PR A -2
C9 C 0.0000 -0.60535(10) 1.28667(12) 0.0263(4) Uani 1 2 d S . .
C10 C 0.0000 -0.66624(9) 1.33113(10) 0.0195(4) Uani 1 2 d S . .
C11 C 0.13005(8) -0.23063(8) 0.75058(9) 0.0363(4) Uani 1 1 d . . .
H11A H 0.1413 -0.2715 0.7662 0.044 Uiso 1 1 calc R . .
C12 C 0.15063(9) -0.20818(9) 0.68791(10) 0.0451(5) Uani 1 1 d . . .
H12A H 0.1763 -0.2326 0.6631 0.054 Uiso 1 1 calc R . .
C13 C 0.13226(6) -0.14813(7) 0.66213(8) 0.0310(3) Uani 1 1 d . . .
C14 C 0.09376(7) -0.11429(8) 0.70092(9) 0.0332(4) Uani 1 1 d . . .
H14A H 0.0799 -0.0747 0.6848 0.040 Uiso 1 1 calc R . .
C15 C 0.07603(6) -0.13988(8) 0.76396(8) 0.0277(3) Uani 1 1 d . . .
H15A H 0.0500 -0.1167 0.7894 0.033 Uiso 1 1 calc R . .
C16 C 0.33877(6) -0.17017(7) 0.39647(10) 0.0302(3) Uani 1 1 d . . .
H16A H 0.3577 -0.1524 0.3587 0.036 Uiso 1 1 calc R . .
C17 C 0.29454(7) -0.13531(9) 0.42303(9) 0.0390(4) Uani 1 1 d . . .
H17A H 0.2838 -0.0960 0.4029 0.047 Uiso 1 1 calc R . .
C18 C 0.26685(7) -0.16060(8) 0.48043(9) 0.0328(4) Uani 1 1 d . . .
C19 C 0.28653(9) -0.21796(9) 0.50979(12) 0.0524(6) Uani 1 1 d . . .
H19A H 0.2700 -0.2357 0.5493 0.063 Uiso 1 1 calc R . .
C20 C 0.33086(9) -0.24796(10) 0.47938(11) 0.0505(6) Uani 1 1 d . . .
H20A H 0.3446 -0.2855 0.5005 0.061 Uiso 1 1 calc R . .
C21 C 0.07659(6) 0.10838(8) 0.48492(8) 0.0259(3) Uani 1 1 d . . .
H21A H 0.0461 0.1290 0.5043 0.031 Uiso 1 1 calc R . .
C22 C 0.09418(7) 0.05024(8) 0.51432(9) 0.0326(4) Uani 1 1 d . . .
H22A H 0.0762 0.0328 0.5530 0.039 Uiso 1 1 calc R . .
C23 C 0.13881(7) 0.01858(7) 0.48549(8) 0.0313(3) Uani 1 1 d . . .
C24 C 0.16484(7) 0.04738(9) 0.42836(10) 0.0436(5) Uani 1 1 d . . .
H24A H 0.1950 0.0274 0.4076 0.052 Uiso 1 1 calc R . .
C25 C 0.14528(6) 0.10594(8) 0.40299(9) 0.0341(4) Uani 1 1 d . . .
H25A H 0.1634 0.1252 0.3654 0.041 Uiso 1 1 calc R . .
C26 C 0.15589(7) -0.12155(8) 0.59752(9) 0.0361(4) Uani 1 1 d . . .
C27 C 0.21938(7) -0.12692(8) 0.51174(9) 0.0367(4) Uani 1 1 d . . .
C28 C 0.16006(7) -0.04251(8) 0.51536(8) 0.0350(4) 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 1.9797(6) . ?
Ni1 O3 2.0392(9) 2_544 ?
Ni1 O2 2.0501(11) . ?
Ni1 N1 2.0918(12) . ?
Ni1 N3 2.1076(11) 3 ?
Ni1 N2 2.1337(13) 6_545 ?
O1 Ni1 1.9797(6) 4 ?
O2 C1 1.2511(13) . ?
O3 C10 1.2445(13) . ?
O3 Ni1 2.0392(9) 2_545 ?
N1 C11 1.3390(19) . ?
N1 C15 1.3509(19) . ?
N2 C16 1.3111(18) . ?
N2 C20 1.342(2) . ?
N2 Ni1 2.1337(13) 6_544 ?
N3 C25 1.3413(17) . ?
N3 C21 1.3414(18) . ?
N3 Ni1 2.1076(11) 3_554 ?
N4 C26 1.3334(19) . ?
N4 C28 1.3495(18) . ?
N5 C27 1.3345(19) . ?
N5 C26 1.3374(18) . ?
N6 C27 1.3402(19) . ?
N6 C28 1.3404(18) . ?
C1 O2 1.2511(13) 4 ?
C1 C2 1.512(3) . ?
C2 C3 1.368(2) . ?
C2 C3 1.368(2) 4 ?
C3 C4 1.389(2) . ?
C4 C5 1.366(2) . ?
C5 C4 1.366(2) 4 ?
C5 C6 1.504(3) . ?
C6 C7A 1.380(4) . ?
C6 C7A 1.380(4) 4 ?
C6 C7B 1.407(4) . ?
C6 C7B 1.407(4) 4 ?
C7A C8A 1.404(6) . ?
C8A C9 1.378(4) . ?
C7B C8B 1.363(5) . ?
C8B C9 1.411(4) . ?
C9 C8A 1.378(4) 4 ?
C9 C8B 1.411(4) 4 ?
C9 C10 1.509(3) . ?
C10 O3 1.2445(13) 4 ?
C11 C12 1.376(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.381(2) . ?
C13 C26 1.466(2) . ?
C14 C15 1.382(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.387(2) . ?
C18 C19 1.387(2) . ?
C18 C27 1.473(2) . ?
C19 C20 1.371(2) . ?
C21 C22 1.384(2) . ?
C22 C23 1.380(2) . ?
C23 C24 1.393(2) . ?
C23 C28 1.469(2) . ?
C24 C25 1.378(2) . ?

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 95.55(4) . 2_544 ?
O1 Ni1 O2 91.79(4) . . ?
O3 Ni1 O2 92.63(4) 2_544 . ?
O1 Ni1 N1 88.22(4) . . ?
O3 Ni1 N1 86.93(5) 2_544 . ?
O2 Ni1 N1 179.56(5) . . ?
O1 Ni1 N3 87.30(4) . 3 ?
O3 Ni1 N3 174.91(4) 2_544 3 ?
O2 Ni1 N3 91.49(4) . 3 ?
N1 Ni1 N3 88.95(5) . 3 ?
O1 Ni1 N2 173.30(5) . 6_545 ?
O3 Ni1 N2 87.61(4) 2_544 6_545 ?
O2 Ni1 N2 82.15(5) . 6_545 ?
N1 Ni1 N2 97.86(5) . 6_545 ?
N3 Ni1 N2 90.01(4) 3 6_545 ?
Ni1 O1 Ni1 119.61(5) . 4 ?
C1 O2 Ni1 128.70(10) . . ?
C10 O3 Ni1 132.73(10) . 2_545 ?
C11 N1 C15 116.78(12) . . ?
C11 N1 Ni1 123.99(10) . . ?
C15 N1 Ni1 119.17(9) . . ?
C16 N2 C20 116.37(13) . . ?
C16 N2 Ni1 125.07(10) . 6_544 ?
C20 N2 Ni1 116.98(11) . 6_544 ?
C25 N3 C21 117.25(12) . . ?
C25 N3 Ni1 123.60(9) . 3_554 ?
C21 N3 Ni1 119.14(9) . 3_554 ?
C26 N4 C28 114.51(12) . . ?
C27 N5 C26 115.12(12) . . ?
C27 N6 C28 114.42(12) . . ?
O2 C1 O2 127.43(17) . 4 ?
O2 C1 C2 116.28(8) . . ?
O2 C1 C2 116.28(8) 4 . ?
C3 C2 C3 118.1(2) . 4 ?
C3 C2 C1 120.90(10) . . ?
C3 C2 C1 120.90(10) 4 . ?
C2 C3 C4 120.72(17) . . ?
C5 C4 C3 121.42(18) . . ?
C4 C5 C4 117.5(2) 4 . ?
C4 C5 C6 120.86(11) 4 . ?
C4 C5 C6 120.86(11) . . ?
C7A C6 C7A 108.9(4) . 4 ?
C7A C6 C7B 29.34(18) . . ?
C7A C6 C7B 117.8(3) 4 . ?
C7A C6 C7B 117.8(3) . 4 ?
C7A C6 C7B 29.34(18) 4 4 ?
C7B C6 C7B 110.5(3) . 4 ?
C7A C6 C5 120.5(2) . . ?
C7A C6 C5 120.5(2) 4 . ?
C7B C6 C5 121.59(18) . . ?
C7B C6 C5 121.59(18) 4 . ?
C6 C7A C8A 121.3(3) . . ?
C9 C8A C7A 120.1(3) . . ?
C8B C7B C6 121.4(3) . . ?
C7B C8B C9 120.5(3) . . ?
C8A C9 C8A 111.7(4) . 4 ?
C8A C9 C8B 29.22(18) . . ?
C8A C9 C8B 118.7(2) 4 . ?
C8A C9 C8B 118.7(2) . 4 ?
C8A C9 C8B 29.22(18) 4 4 ?
C8B C9 C8B 109.7(3) . 4 ?
C8A C9 C10 120.86(18) . . ?
C8A C9 C10 120.86(18) 4 . ?
C8B C9 C10 120.34(17) . . ?
C8B C9 C10 120.34(17) 4 . ?
O3 C10 O3 127.78(17) 4 . ?
O3 C10 C9 116.11(9) 4 . ?
O3 C10 C9 116.11(9) . . ?
N1 C11 C12 123.68(14) . . ?
C11 C12 C13 118.93(15) . . ?
C14 C13 C12 118.00(14) . . ?
C14 C13 C26 122.10(13) . . ?
C12 C13 C26 119.83(13) . . ?
C13 C14 C15 119.27(14) . . ?
N1 C15 C14 123.20(13) . . ?
N2 C16 C17 124.41(14) . . ?
C18 C17 C16 118.29(14) . . ?
C19 C18 C17 117.89(14) . . ?
C19 C18 C27 120.23(14) . . ?
C17 C18 C27 121.84(13) . . ?
C20 C19 C18 118.70(16) . . ?
N2 C20 C19 124.01(16) . . ?
N3 C21 C22 123.24(13) . . ?
C23 C22 C21 119.06(13) . . ?
C22 C23 C24 118.16(13) . . ?
C22 C23 C28 121.49(13) . . ?
C24 C23 C28 120.30(13) . . ?
C25 C24 C23 119.11(14) . . ?
N3 C25 C24 123.15(13) . . ?
N4 C26 N5 125.26(13) . . ?
N4 C26 C13 117.46(13) . . ?
N5 C26 C13 117.28(13) . . ?
N5 C27 N6 125.32(13) . . ?
N5 C27 C18 116.45(13) . . ?
N6 C27 C18 118.22(13) . . ?
N6 C28 N4 125.30(13) . . ?
N6 C28 C23 117.33(13) . . ?
N4 C28 C23 117.36(13) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.046

# Start Validation Reply Form

_vrf_CHEMW03_1                   
;
PROBLEM: The ratio of given/expected molecular weight as 
calculated from the _atom_site* data lies outside
the range 0.90 <> 1.10
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_weight 1558.94
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 50.00 600.55
H 1.01 32.00 32.26
N 14.01 12.00 168.08
O 16.00 5.00 79.99
Ni 58.69 2.00 117.38
Calculated formula weight 998.26
RESPONSE: The contribution of the disordered solvent molecules removed
by the SQUEEZE process was included in the overall formula.
;

