# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_ceknimof_sq
_database_code_depnum_ccdc_archive 'CCDC 1868850'
_audit_update_record             
;
2018-09-20 deposited with the CCDC.
2018-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C208 H224 N64 Ni16 O64'
_chemical_formula_weight         5583.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   19.5487(6)
_cell_length_b                   19.5487(6)
_cell_length_c                   29.8878(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11421.7(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    120549
_cell_measurement_theta_min      2.701
_cell_measurement_theta_max      67.469

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.812
_exptl_crystal_F_000             2880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.099
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6144
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruke Kappa Apex Duo'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            120549
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.701
_diffrn_reflns_theta_max         67.469
_diffrn_reflns_theta_full        67.469
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5106
_reflns_number_gt                4311
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+240.0000P] 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         5106
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.1251
_refine_ls_wR_factor_ref         0.2906
_refine_ls_wR_factor_gt          0.2796
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 -0.65090(13) -0.48383(12) 0.15043(5) 0.0460(8) Uani 0.887(8) 1 d . . P A
1
N1 N -0.7044(4) -0.5274(4) 0.0965(2) 0.0467(17) Uani 1 1 d . . . . .
N2 N -0.7682(4) -0.5035(4) 0.0899(2) 0.060(2) Uani 1 1 d . . . . .
N3 N -0.7078(4) -0.3975(5) 0.1461(2) 0.061(2) Uani 1 1 d . . . . .
N4 N -0.7744(4) -0.3973(4) 0.1319(2) 0.0498(17) Uani 1 1 d . . . . .
O1 O -0.7738(4) -0.5420(4) -0.0479(2) 0.0655(18) Uani 1 1 d . . . . .
O2 O -0.7023(4) -0.6244(4) -0.0326(2) 0.074(2) Uani 1 1 d . . . . .
O3 O -0.6980(4) -0.1822(4) 0.1351(2) 0.069(2) Uani 1 1 d . . . . .
O4 O -0.7959(3) -0.1888(3) 0.1002(2) 0.0593(17) Uani 1 1 d . . . . .
C1 C -0.7380(6) -0.5751(6) -0.0202(3) 0.065(3) Uani 1 1 d . . . . .
C2 C -0.6223(6) -0.5921(7) 0.0529(4) 0.081(4) Uani 1 1 d . . . . .
H2A H -0.601377 -0.598750 0.082413 0.122 Uiso 1 1 calc R U . . .
H2B H -0.591968 -0.564225 0.034254 0.122 Uiso 1 1 calc R U . . .
H2C H -0.629497 -0.636667 0.038666 0.122 Uiso 1 1 calc R U . . .
C3 C -0.6858(6) -0.5585(6) 0.0579(3) 0.063(3) Uani 1 1 d . . . . .
C4 C -0.7378(6) -0.5525(6) 0.0270(3) 0.067(3) Uani 1 1 d . . . . .
C5 C -0.7914(5) -0.5146(6) 0.0474(3) 0.059(3) Uani 1 1 d . . . . .
C6 C -0.8570(6) -0.4876(8) 0.0298(4) 0.095(4) Uani 1 1 d . . . . .
H6A H -0.894448 -0.501455 0.049617 0.143 Uiso 1 1 calc R U . . .
H6B H -0.864978 -0.505955 -0.000251 0.143 Uiso 1 1 calc R U . . .
H6C H -0.854828 -0.437566 0.028421 0.143 Uiso 1 1 calc R U . . .
C7 C -0.8046(5) -0.4670(5) 0.1259(4) 0.064(3) Uani 1 1 d . . . . .
H7A H -0.800910 -0.493174 0.154110 0.077 Uiso 1 1 calc R U . A 2
H7B H -0.853726 -0.462904 0.118133 0.077 Uiso 1 1 calc R U . A 2
C8 C -0.6246(6) -0.3078(6) 0.1610(4) 0.080(3) Uani 1 1 d . . . . .
H8A H -0.594002 -0.347378 0.163229 0.120 Uiso 1 1 calc R U . . .
H8B H -0.629422 -0.286496 0.190517 0.120 Uiso 1 1 calc R U . . .
H8C H -0.605306 -0.274527 0.139951 0.120 Uiso 1 1 calc R U . . .
C9 C -0.6932(6) -0.3306(5) 0.1447(3) 0.061(3) Uani 1 1 d . . . . .
C10 C -0.7456(5) -0.2911(5) 0.1284(3) 0.055(2) Uani 1 1 d . . . . .
C11 C -0.7999(5) -0.3364(5) 0.1204(3) 0.056(2) Uani 1 1 d . . . . .
C12 C -0.8686(6) -0.3280(7) 0.1048(4) 0.083(4) Uani 1 1 d . . . . .
H12A H -0.895675 -0.368293 0.112984 0.125 Uiso 1 1 calc R U . . .
H12B H -0.868399 -0.322900 0.072153 0.125 Uiso 1 1 calc R U . . .
H12C H -0.888698 -0.287158 0.118458 0.125 Uiso 1 1 calc R U . . .
C13 C -0.7470(6) -0.2199(5) 0.1206(3) 0.061(3) Uani 1 1 d . . . . .
Ni1A Ni -0.6897(10) -0.4551(8) 0.1450(4) 0.047(5) Uani 0.113(8) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N3 2.025(11) . ?
Ni1 O1 2.059(7) 3_355 ?
Ni1 O3 2.063(7) 12_566 ?
Ni1 N1 2.102(7) . ?
Ni1 O4 2.132(7) 12_566 ?
Ni1 O2 2.151(7) 3_355 ?
Ni1 C1 2.419(10) 3_355 ?
Ni1 C13 2.458(10) 12_566 ?
N1 N2 1.347(10) . ?
N1 C3 1.354(11) . ?
N1 Ni1A 2.045(14) . ?
N2 C5 1.364(11) . ?
N2 C7 1.473(12) . ?
N2 Ni1A 2.443(17) . ?
N3 Ni1A 1.181(19) . ?
N3 C9 1.338(13) . ?
N3 N4 1.369(10) . ?
N4 C11 1.336(12) . ?
N4 C7 1.497(12) . ?
N4 Ni1A 2.04(2) . ?
O1 C1 1.263(12) . ?
O1 Ni1A 2.199(16) 4_434 ?
O2 C1 1.246(12) . ?
O3 C13 1.284(12) . ?
O4 C13 1.287(12) . ?
C1 C4 1.480(12) . ?
C2 C3 1.412(14) . ?
C3 C4 1.379(14) . ?
C4 C5 1.420(14) . ?
C5 C6 1.484(14) . ?
C7 Ni1A 2.33(2) . ?
C8 C9 1.497(14) . ?
C9 C10 1.372(14) . ?
C9 Ni1A 2.435(18) . ?
C10 C11 1.403(14) . ?
C10 C13 1.411(13) . ?
C11 C12 1.431(14) . ?

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
N3 Ni1 O1 93.8(3) . 3_355 ?
N3 Ni1 O3 96.7(3) . 12_566 ?
O1 Ni1 O3 160.4(3) 3_355 12_566 ?
N3 Ni1 N1 90.9(3) . . ?
O1 Ni1 N1 98.7(3) 3_355 . ?
O3 Ni1 N1 97.7(3) 12_566 . ?
N3 Ni1 O4 157.7(3) . 12_566 ?
O1 Ni1 O4 103.7(3) 3_355 12_566 ?
O3 Ni1 O4 62.7(3) 12_566 12_566 ?
N1 Ni1 O4 99.9(3) . 12_566 ?
N3 Ni1 O2 86.9(3) . 3_355 ?
O1 Ni1 O2 62.4(3) 3_355 3_355 ?
O3 Ni1 O2 101.6(3) 12_566 3_355 ?
N1 Ni1 O2 160.7(3) . 3_355 ?
O4 Ni1 O2 89.0(3) 12_566 3_355 ?
N3 Ni1 C1 89.1(4) . 3_355 ?
O1 Ni1 C1 31.5(3) 3_355 3_355 ?
O3 Ni1 C1 132.0(4) 12_566 3_355 ?
N1 Ni1 C1 129.9(3) . 3_355 ?
O4 Ni1 C1 98.5(3) 12_566 3_355 ?
O2 Ni1 C1 30.9(3) 3_355 3_355 ?
N3 Ni1 C13 126.8(4) . 12_566 ?
O1 Ni1 C13 132.3(3) 3_355 12_566 ?
O3 Ni1 C13 31.5(3) 12_566 12_566 ?
N1 Ni1 C13 103.9(3) . 12_566 ?
O4 Ni1 C13 31.6(3) 12_566 12_566 ?
O2 Ni1 C13 92.7(3) 3_355 12_566 ?
C1 Ni1 C13 115.7(4) 3_355 12_566 ?
N2 N1 C3 106.3(7) . . ?
N2 N1 Ni1A 89.7(7) . . ?
C3 N1 Ni1A 151.2(9) . . ?
N2 N1 Ni1 115.7(5) . . ?
C3 N1 Ni1 134.5(7) . . ?
N1 N2 C5 112.8(7) . . ?
N1 N2 C7 120.5(7) . . ?
C5 N2 C7 126.6(9) . . ?
N1 N2 Ni1A 56.8(6) . . ?
C5 N2 Ni1A 153.8(8) . . ?
C7 N2 Ni1A 67.9(6) . . ?
Ni1A N3 C9 150.1(13) . . ?
Ni1A N3 N4 106.2(11) . . ?
C9 N3 N4 100.9(9) . . ?
C9 N3 Ni1 134.4(8) . . ?
N4 N3 Ni1 123.0(7) . . ?
C11 N4 N3 116.0(8) . . ?
C11 N4 C7 129.2(8) . . ?
N3 N4 C7 114.2(8) . . ?
C11 N4 Ni1A 147.7(8) . . ?
N3 N4 Ni1A 33.7(6) . . ?
C7 N4 Ni1A 80.8(7) . . ?
C1 O1 Ni1 90.2(6) . 4_434 ?
C1 O1 Ni1A 95.0(7) . 4_434 ?
Ni1 O1 Ni1A 25.7(5) 4_434 4_434 ?
C1 O2 Ni1 86.5(6) . 4_434 ?
C13 O3 Ni1 91.4(6) . 15_545 ?
C13 O4 Ni1 88.3(6) . 15_545 ?
O2 C1 O1 120.8(9) . . ?
O2 C1 C4 120.9(10) . . ?
O1 C1 C4 118.3(10) . . ?
O2 C1 Ni1 62.6(5) . 4_434 ?
O1 C1 Ni1 58.3(5) . 4_434 ?
C4 C1 Ni1 173.4(8) . 4_434 ?
N1 C3 C4 109.4(9) . . ?
N1 C3 C2 122.4(9) . . ?
C4 C3 C2 128.1(10) . . ?
C3 C4 C5 107.5(8) . . ?
C3 C4 C1 128.0(11) . . ?
C5 C4 C1 124.3(10) . . ?
N2 C5 C4 103.8(8) . . ?
N2 C5 C6 124.0(8) . . ?
C4 C5 C6 132.1(8) . . ?
N2 C7 N4 109.8(8) . . ?
N2 C7 Ni1A 76.2(6) . . ?
N4 C7 Ni1A 59.9(6) . . ?
N3 C9 C10 113.8(10) . . ?
N3 C9 C8 118.1(10) . . ?
C10 C9 C8 128.1(10) . . ?
N3 C9 Ni1A 14.0(7) . . ?
C10 C9 Ni1A 125.9(9) . . ?
C8 C9 Ni1A 105.7(9) . . ?
C9 C10 C11 105.6(9) . . ?
C9 C10 C13 129.0(10) . . ?
C11 C10 C13 125.4(10) . . ?
N4 C11 C10 103.6(9) . . ?
N4 C11 C12 122.5(10) . . ?
C10 C11 C12 133.9(11) . . ?
O3 C13 O4 116.2(9) . . ?
O3 C13 C10 119.8(10) . . ?
O4 C13 C10 124.0(10) . . ?
O3 C13 Ni1 57.1(5) . 15_545 ?
O4 C13 Ni1 60.1(5) . 15_545 ?
C10 C13 Ni1 171.1(8) . 15_545 ?
N3 Ni1A N4 40.1(8) . . ?
N3 Ni1A N1 129.5(12) . . ?
N4 Ni1A N1 97.6(8) . . ?
N3 Ni1A O1 120.8(10) . 3_355 ?
N4 Ni1A O1 110.7(8) . 3_355 ?
N1 Ni1A O1 96.1(7) . 3_355 ?
N3 Ni1A C7 79.2(11) . . ?
N4 Ni1A C7 39.4(5) . . ?
N1 Ni1A C7 67.7(6) . . ?
O1 Ni1A C7 88.4(7) 3_355 . ?
N3 Ni1A C9 15.9(7) . . ?
N4 Ni1A C9 54.7(5) . . ?
N1 Ni1A C9 133.1(8) . . ?
O1 Ni1A C9 127.5(6) 3_355 . ?
C7 Ni1A C9 94.1(8) . . ?
N3 Ni1A N2 101.5(11) . . ?
N4 Ni1A N2 64.9(6) . . ?
N1 Ni1A N2 33.5(3) . . ?
O1 Ni1A N2 100.6(7) 3_355 . ?
C7 Ni1A N2 35.8(4) . . ?
C9 Ni1A N2 111.5(8) . . ?

_refine_diff_density_max         0.894
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.144




