# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1884968'
loop_
_audit_author_name
_audit_author_address
'yang mei'
; Soochow University
China
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-03-14 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            'C81 H110 N24 Ni6 O9 S12'
_chemical_formula_weight         2300.90

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'
S S 0.1246 0.1234 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   20.6684(13)
_cell_length_b                   20.6684(13)
_cell_length_c                   24.235(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8965.9(13)
_cell_formula_units_Z            3
_cell_measurement_temperature    216(2)
_cell_measurement_reflns_used    4577
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.85

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             3588
_exptl_transmission_factor_min   0.5912
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.190
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      216(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14521
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3649
_reflns_number_gt                2482
_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0700P)²+0.3160P] 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         3649
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.41702(2) 0.86390(2) 0.66142(2) 0.02744(18) Uani 1 1 d . . . . .
S1 S 0.31594(5) 0.76210(4) 0.60718(4) 0.0268(2) Uani 1 1 d . . . . .
S2 S 0.52899(5) 0.87765(5) 0.61588(4) 0.0327(2) Uani 1 1 d . . . . .
N1 N 0.39150(16) 0.90502(16) 0.59106(12) 0.0314(7) Uani 1 1 d . . . . .
N2 N 0.29957(18) 0.83770(18) 0.52246(13) 0.0412(8) Uani 1 1 d . . . . .
N3 N 0.51376(16) 0.95800(15) 0.69031(13) 0.0353(7) Uani 1 1 d . . . . .
N4 N 0.64057(17) 0.99621(17) 0.66806(14) 0.0429(8) Uani 1 1 d . . . . .
O1 O 0.2110(2) 0.70642(19) 0.46083(16) 0.0828(12) Uani 1 1 d . . . . .
H1 H 0.2397 0.7443 0.4780 0.124 Uiso 1 1 calc R U . . .
C1 C 0.33593(19) 0.8411(2) 0.56890(15) 0.0304(8) Uani 1 1 d . . . . .
C2 C 0.2768(3) 0.8989(3) 0.4454(2) 0.0812(17) Uani 1 1 d . . . . .
H2A H 0.2921 0.9485 0.4327 0.122 Uiso 1 1 calc R U . . .
H2B H 0.2246 0.8736 0.4542 0.122 Uiso 1 1 calc R U . . .
H2C H 0.2857 0.8719 0.4169 0.122 Uiso 1 1 calc R U . . .
C3 C 0.3210(3) 0.9030(3) 0.49607(17) 0.0491(11) Uani 1 1 d . . . . .
C4 C 0.3788(2) 0.9686(2) 0.51525(18) 0.0495(11) Uani 1 1 d . . . . .
H4 H 0.3948 1.0126 0.4954 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4139(2) 0.9696(2) 0.56438(17) 0.0400(10) Uani 1 1 d . . . . .
C6 C 0.4746(3) 1.0385(2) 0.5892(2) 0.0576(12) Uani 1 1 d . . . . .
H6A H 0.4635 1.0409 0.6274 0.086 Uiso 1 1 calc R U . . .
H6B H 0.4791 1.0812 0.5701 0.086 Uiso 1 1 calc R U . . .
H6C H 0.5208 1.0381 0.5864 0.086 Uiso 1 1 calc R U . . .
C7 C 0.5663(2) 0.95248(19) 0.66260(16) 0.0343(9) Uani 1 1 d . . . . .
C8 C 0.4783(3) 1.0203(3) 0.7606(2) 0.0628(14) Uani 1 1 d . . . . .
H8A H 0.4425 1.0211 0.7357 0.094 Uiso 1 1 calc R U . . .
H8B H 0.5017 1.0658 0.7816 0.094 Uiso 1 1 calc R U . . .
H8C H 0.4533 0.9785 0.7851 0.094 Uiso 1 1 calc R U . . .
C9 C 0.5358(2) 1.0136(2) 0.72864(18) 0.0463(10) Uani 1 1 d . . . . .
C10 C 0.6122(2) 1.0609(2) 0.7370(2) 0.0546(12) Uani 1 1 d . . . . .
H10 H 0.6290 1.0990 0.7629 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6625(2) 1.0505(2) 0.7063(2) 0.0501(12) Uani 1 1 d . . . . .
C12 C 0.7454(2) 1.0983(3) 0.7145(2) 0.0690(15) Uani 1 1 d . . . . .
H12A H 0.7710 1.0838 0.6887 0.104 Uiso 1 1 calc R U . . .
H12B H 0.7581 1.0918 0.7514 0.104 Uiso 1 1 calc R U . . .
H12C H 0.7601 1.1498 0.7087 0.104 Uiso 1 1 calc R U . . .
C13 C 0.2134(3) 0.6447(3) 0.4832(2) 0.0748(16) Uani 1 1 d . . . . .
H13A H 0.2561 0.6621 0.5069 0.112 Uiso 1 1 calc R U . . .
H13B H 0.2170 0.6155 0.4538 0.112 Uiso 1 1 calc R U . . .
H13C H 0.1687 0.6144 0.5040 0.112 Uiso 1 1 calc R U . . .
O2 O 0.2476(5) 0.7375(5) 0.3515(4) 0.098(3) Uiso 0.5 1 d . . P . .
C14 C 0.3188(8) 0.7706(8) 0.3512(6) 0.101(4) Uiso 0.5 1 d . . P . .


_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 N1 2.087(3) . ?
Ni1 N3 2.093(3) . ?
Ni1 S2 2.4426(10) 15_556 ?
Ni1 S1 2.4466(10) 14_456 ?
Ni1 S2 2.4488(10) . ?
Ni1 S1 2.4746(10) . ?
S1 C1 1.739(4) . ?
S1 Ni1 2.4468(10) 15_556 ?
S2 C7 1.754(4) . ?
S2 Ni1 2.4425(10) 14_456 ?
N1 C5 1.341(4) . ?
N1 C1 1.355(5) . ?
N2 C1 1.335(5) . ?
N2 C3 1.353(5) . ?
N3 C7 1.330(5) . ?
N3 C9 1.366(5) . ?
N4 C7 1.342(5) . ?
N4 C11 1.347(6) . ?
O1 C13 1.410(6) . ?
O1 H1 0.8200 . ?
C2 C3 1.508(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.365(6) . ?
C4 C5 1.388(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.476(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.483(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.395(6) . ?
C10 C11 1.379(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.503(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O2 C14 1.275(15) . ?

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
N1 Ni1 N3 102.32(12) . . ?
N1 Ni1 S2 94.53(8) . 15_556 ?
N3 Ni1 S2 103.36(9) . 15_556 ?
N1 Ni1 S1 161.71(8) . 14_456 ?
N3 Ni1 S1 93.37(8) . 14_456 ?
S2 Ni1 S1 90.87(3) 15_556 14_456 ?
N1 Ni1 S2 90.06(8) . . ?
N3 Ni1 S2 68.58(9) . . ?
S2 Ni1 S2 171.47(3) 15_556 . ?
S1 Ni1 S2 86.95(3) 14_456 . ?
N1 Ni1 S1 68.56(8) . . ?
N3 Ni1 S1 167.36(9) . . ?
S2 Ni1 S1 86.47(3) 15_556 . ?
S1 Ni1 S1 94.41(4) 14_456 . ?
S2 Ni1 S1 101.91(3) . . ?
C1 S1 Ni1 103.60(12) . 15_556 ?
C1 S1 Ni1 77.40(13) . . ?
Ni1 S1 Ni1 92.43(3) 15_556 . ?
C7 S2 Ni1 100.76(12) . 14_456 ?
C7 S2 Ni1 77.60(13) . . ?
Ni1 S2 Ni1 93.16(3) 14_456 . ?
C5 N1 C1 118.8(3) . . ?
C5 N1 Ni1 140.2(3) . . ?
C1 N1 Ni1 101.0(2) . . ?
C1 N2 C3 116.8(4) . . ?
C7 N3 C9 118.2(3) . . ?
C7 N3 Ni1 101.1(2) . . ?
C9 N3 Ni1 140.4(3) . . ?
C7 N4 C11 115.1(4) . . ?
C13 O1 H1 109.5 . . ?
N2 C1 N1 124.5(3) . . ?
N2 C1 S1 122.5(3) . . ?
N1 C1 S1 113.1(3) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 121.2(4) . . ?
N2 C3 C2 116.2(4) . . ?
C4 C3 C2 122.6(4) . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 118.8(4) . . ?
N1 C5 C6 117.8(4) . . ?
C4 C5 C6 123.4(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 N4 126.9(3) . . ?
N3 C7 S2 112.5(3) . . ?
N4 C7 S2 120.6(3) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 118.2(4) . . ?
N3 C9 C8 119.2(4) . . ?
C10 C9 C8 122.6(4) . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N4 C11 C10 122.3(4) . . ?
N4 C11 C12 115.9(4) . . ?
C10 C11 C12 121.8(4) . . ?
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 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.073



