# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1540217'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_audit_creation_date             2017-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N6 Ni O6 S2, 2(C9 H6 N2 O2)'
_chemical_formula_sum            'C38 H28 N10 Ni O10 S2'
_chemical_formula_weight         907.53
_chemical_melting_point          ?
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'
Ni Ni -3.0029 0.5091 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0112(3)
_cell_length_b                   8.0734(3)
_cell_length_c                   14.9981(5)
_cell_angle_alpha                82.284(3)
_cell_angle_beta                 81.302(3)
_cell_angle_gamma                76.188(3)
_cell_volume                     926.28(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    27333
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.75
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.478
_exptl_absorpt_coefficient_mu    2.473
_exptl_absorpt_correction_T_max  0.580
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   X-AREA
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22071
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.342
_diffrn_reflns_theta_min         2.996
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3078
_reflns_number_total             3495
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1W-H1WA = O1W-H1WB
 0.84 with sigma of 0.001
 H1WA-H1WB
 1.365 with sigma of 0.02
3. Others
 Fixed Sof: O2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5) O7(0.5) O8(0.5) O9(0.5)
4.a Riding coordinates:
 O1W(H1WA,H1WB)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 1.000000 0.000000 0.01340(12) Uani 1 2 d S . P . .
S1 S 1.09339(5) 0.69864(5) -0.04588(3) 0.02199(13) Uani 1 1 d . . . . .
O1W O 0.44941(14) 0.75826(13) 0.00393(7) 0.0170(2) Uani 1 1 d D . . . .
H1WA H 0.348172 0.752863 -0.001726 0.025 Uiso 1 1 d DR U . . .
H1WB H 0.483340 0.682411 0.045440 0.025 Uiso 1 1 d DR U . . .
N1 N 0.48082(16) 0.98749(15) 0.14948(8) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.75276(17) 0.87770(17) 0.00107(8) 0.0170(3) Uani 1 1 d . . . . .
N3 N 0.23891(19) 0.87146(17) 0.46953(9) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.6112(2) 1.03329(19) 0.17659(10) 0.0161(3) Uani 1 1 d . . . . .
H1 H 0.698779 1.063472 0.131506 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6289(2) 1.04026(19) 0.26761(10) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.724006 1.077790 0.282499 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5089(2) 0.99294(18) 0.33461(10) 0.0160(3) Uani 1 1 d . . . . .
H3 H 0.519893 0.995171 0.396590 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3671(2) 0.94027(18) 0.30956(10) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.2322(2) 0.88630(19) 0.37165(10) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.0952(2) 0.8419(2) 0.34461(11) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.007950 0.806777 0.388189 0.023 Uiso 1 1 calc R U . . .
C7 C 0.0846(2) 0.8487(2) 0.25144(11) 0.0189(3) Uani 1 1 d . . . . .
H7 H -0.011576 0.820132 0.232072 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2119(2) 0.89631(19) 0.18812(10) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.204192 0.898025 0.125402 0.020 Uiso 1 1 calc R U . . .
C9 C 0.35450(19) 0.94288(18) 0.21563(10) 0.0142(3) Uani 1 1 d . . . . .
C10 C 0.8953(2) 0.80398(19) -0.01674(9) 0.0154(3) Uani 1 1 d . . . . .
O2 O 0.3966(3) 0.8182(3) 0.49676(14) 0.0195(5) Uani 0.5 1 d . . P A 1
O3 O 0.1163(3) 0.8846(3) 0.52453(14) 0.0209(5) Uani 0.5 1 d . . P A 1
O4 O 0.1842(3) 0.7563(3) 0.51513(15) 0.0227(5) Uani 0.5 1 d . . P A 2
O5 O 0.2643(3) 0.9986(3) 0.49724(14) 0.0194(5) Uani 0.5 1 d . . P A 2
N4 N 0.53753(17) 0.53980(16) 0.15676(9) 0.0181(3) Uani 1 1 d . . . . .
N5 N 0.25645(19) 0.36784(17) 0.45967(9) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.6639(2) 0.57371(19) 0.19302(11) 0.0189(3) Uani 1 1 d . . . . .
H11 H 0.752544 0.615692 0.153646 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6750(2) 0.55131(19) 0.28672(11) 0.0194(3) Uani 1 1 d . . . . .
H12 H 0.770168 0.575485 0.309421 0.023 Uiso 1 1 calc R U . . .
C13 C 0.5474(2) 0.49443(19) 0.34446(10) 0.0182(3) Uani 1 1 d . . . . .
H13 H 0.551301 0.480986 0.408065 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4092(2) 0.45563(18) 0.30904(10) 0.0165(3) Uani 1 1 d . . . . .
C15 C 0.2670(2) 0.39513(19) 0.36071(11) 0.0183(3) Uani 1 1 d . . . . .
C16 C 0.1387(2) 0.3570(2) 0.32239(12) 0.0225(4) Uani 1 1 d . . . . .
H16 H 0.046379 0.316844 0.359417 0.027 Uiso 1 1 calc R U . . .
C17 C 0.1445(2) 0.3779(2) 0.22738(12) 0.0239(4) Uani 1 1 d . . . . .
H17 H 0.055937 0.351069 0.200096 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2773(2) 0.4366(2) 0.17402(11) 0.0210(3) Uani 1 1 d . . . . .
H18 H 0.280397 0.449731 0.109926 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4099(2) 0.47804(19) 0.21368(10) 0.0165(3) Uani 1 1 d . . . . .
O6 O 0.2594(3) 0.4886(3) 0.49572(14) 0.0203(5) Uani 0.5 1 d . . P B 1
O7 O 0.2134(3) 0.2345(3) 0.49254(15) 0.0218(5) Uani 0.5 1 d . . P B 1
O8 O 0.1274(3) 0.3957(3) 0.51092(16) 0.0242(5) Uani 0.5 1 d . . P B 2
O9 O 0.4065(3) 0.3043(3) 0.49610(15) 0.0230(5) Uani 0.5 1 d . . P B 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 O1W 2.0776(10) . ?
Ni1 O1W 2.0776(10) 2_675 ?
Ni1 N1 2.2141(12) . ?
Ni1 N1 2.2142(12) 2_675 ?
Ni1 N2 2.0314(14) 2_675 ?
Ni1 N2 2.0313(14) . ?
S1 C10 1.6364(16) . ?
O1W H1WA 0.8400 . ?
O1W H1WB 0.8401 . ?
N1 C1 1.322(2) . ?
N1 C9 1.3829(18) . ?
N2 C10 1.164(2) . ?
N3 C5 1.465(2) . ?
N3 O2 1.341(3) . ?
N3 O3 1.177(3) . ?
N3 O4 1.207(2) . ?
N3 O5 1.228(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.364(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.419(2) . ?
C4 C5 1.427(2) . ?
C4 C9 1.425(2) . ?
C5 C6 1.364(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.406(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.417(2) . ?
N4 C11 1.317(2) . ?
N4 C19 1.374(2) . ?
N5 C15 1.463(2) . ?
N5 O6 1.183(3) . ?
N5 O7 1.226(2) . ?
N5 O8 1.186(3) . ?
N5 O9 1.355(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.406(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.362(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.412(2) . ?
C14 C15 1.426(2) . ?
C14 C19 1.417(2) . ?
C15 C16 1.364(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.407(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.417(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
O1W Ni1 O1W 180.0 . 2_675 ?
O1W Ni1 N1 86.84(4) . 2_675 ?
O1W Ni1 N1 93.16(4) 2_675 2_675 ?
O1W Ni1 N1 86.84(4) 2_675 . ?
O1W Ni1 N1 93.16(4) . . ?
N1 Ni1 N1 180.0 . 2_675 ?
N2 Ni1 O1W 93.59(5) 2_675 . ?
N2 Ni1 O1W 93.59(5) . 2_675 ?
N2 Ni1 O1W 86.41(5) 2_675 2_675 ?
N2 Ni1 O1W 86.41(5) . . ?
N2 Ni1 N1 87.44(5) 2_675 2_675 ?
N2 Ni1 N1 92.55(5) . 2_675 ?
N2 Ni1 N1 92.56(5) 2_675 . ?
N2 Ni1 N1 87.45(5) . . ?
N2 Ni1 N2 180.0 . 2_675 ?
Ni1 O1W H1WA 117.7 . . ?
Ni1 O1W H1WB 119.2 . . ?
H1WA O1W H1WB 107.1 . . ?
C1 N1 Ni1 112.62(9) . . ?
C1 N1 C9 117.43(13) . . ?
C9 N1 Ni1 129.94(10) . . ?
C10 N2 Ni1 165.92(12) . . ?
O2 N3 C5 116.28(15) . . ?
O3 N3 C5 124.29(18) . . ?
O3 N3 O2 118.87(19) . . ?
O4 N3 C5 117.13(17) . . ?
O4 N3 O5 126.23(19) . . ?
O5 N3 C5 114.63(15) . . ?
N1 C1 H1 117.8 . . ?
N1 C1 C2 124.30(13) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.73(14) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.45(14) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 124.97(14) . . ?
C3 C4 C9 118.56(13) . . ?
C9 C4 C5 116.47(14) . . ?
C4 C5 N3 120.26(14) . . ?
C6 C5 N3 116.64(13) . . ?
C6 C5 C4 123.08(14) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.15(14) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.72(15) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.48(14) . . ?
C9 C8 H8 119.8 . . ?
N1 C9 C4 121.46(14) . . ?
N1 C9 C8 118.44(13) . . ?
C8 C9 C4 120.08(13) . . ?
N2 C10 S1 177.51(14) . . ?
C11 N4 C19 118.13(13) . . ?
O6 N5 C15 115.36(15) . . ?
O6 N5 O7 129.21(19) . . ?
O7 N5 C15 113.83(16) . . ?
O8 N5 C15 125.55(19) . . ?
O8 N5 O9 117.0(2) . . ?
O9 N5 C15 117.43(15) . . ?
N4 C11 H11 118.1 . . ?
N4 C11 C12 123.72(14) . . ?
C12 C11 H11 118.1 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.04(15) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.49(14) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 125.89(14) . . ?
C13 C14 C19 117.88(14) . . ?
C19 C14 C15 116.23(14) . . ?
C14 C15 N5 119.84(14) . . ?
C16 C15 N5 116.98(14) . . ?
C16 C15 C14 123.17(15) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.27(15) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.34(16) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.53(15) . . ?
C19 C18 H18 119.7 . . ?
N4 C19 C14 121.70(14) . . ?
N4 C19 C18 117.85(14) . . ?
C14 C19 C18 120.45(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
