# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dan9414
_database_code_depnum_ccdc_archive 'CCDC 2054290'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-03-16 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H24 N6 Ni O S3'
_chemical_formula_iupac          ?
_chemical_formula_weight         423.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3663(2)
_cell_length_b                   14.6831(3)
_cell_length_c                   15.5009(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.3820(10)
_cell_angle_gamma                90
_cell_volume                     1878.71(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4466
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888

_exptl_absorpt_coefficient_mu    1.377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21254
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_full        28.20
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_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.

One disordered over two positions DMSO molecule was found in 
the asymmetrical unit. Several restraints (SADI, SAME, ISOR and SIMU) were
used in order to improve refinement stability. 

The hydrogens at N3, N5 and N6 atoms were refined freely. 
;

_reflns_number_total             4553
_reflns_number_gt                3985
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0963
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         4553
_refine_ls_number_parameters     257
_refine_ls_number_restraints     64
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+2.0977P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.729
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.79031(3) 0.54340(2) 0.11659(2) 0.01983(9) Uani d . . . 1.0 . .
S S1 0.79226(7) 0.59339(4) -0.03120(4) 0.02507(14) Uani d . . . 1.0 . .
S S2 0.76002(7) 0.71459(4) 0.11463(4) 0.02520(14) Uani d . . . 1.0 . .
N N1 0.8589(5) 0.7572(2) -0.2022(2) 0.0751(11) Uani d . . . 1.0 . .
N N2 0.7530(4) 0.94264(17) 0.00278(19) 0.0501(7) Uani d . . . 1.0 . .
N N3 0.5361(2) 0.53676(15) 0.11382(14) 0.0245(4) Uani d . . . 1.0 . .
H H3A 0.502(3) 0.591(2) 0.0963(18) 0.025(7) Uiso d . . . 1.0 . .
H H3B 0.485(4) 0.494(2) 0.086(2) 0.032(8) Uiso d . . . 1.0 . .
N N4 0.7919(2) 0.51202(13) 0.24870(13) 0.0230(4) Uani d . . . 1.0 . .
N N5 0.8172(3) 0.40191(14) 0.10417(14) 0.0262(4) Uani d . . . 1.0 . .
H H5A 0.914(4) 0.390(2) 0.110(2) 0.041(9) Uiso d . . . 1.0 . .
H H5B 0.770(4) 0.376(2) 0.054(2) 0.035(8) Uiso d . . . 1.0 . .
N N6 1.0425(3) 0.56165(17) 0.15842(15) 0.0278(4) Uani d . . . 1.0 . .
H H6A 1.068(4) 0.615(2) 0.153(2) 0.042(9) Uiso d . . . 1.0 . .
H H6B 1.107(4) 0.530(2) 0.126(2) 0.047(10) Uiso d . . . 1.0 . .
C C1 0.7803(3) 0.70301(16) 0.00712(15) 0.0231(4) Uani d . . . 1.0 . .
C C2 0.7891(3) 0.77799(17) -0.04780(16) 0.0296(5) Uani d . . . 1.0 . .
C C3 0.8246(4) 0.7670(2) -0.13340(19) 0.0446(7) Uani d . . . 1.0 . .
C C4 0.7698(3) 0.86918(18) -0.01897(18) 0.0344(6) Uani d . . . 1.0 . .
C C11 0.4973(3) 0.52644(19) 0.20370(17) 0.0311(5) Uani d . . . 1.0 . .
H H11A 0.4679 0.4624 0.2134 0.037 Uiso calc U . R 1.0 . .
H H11B 0.4035 0.5654 0.2104 0.037 Uiso calc U . R 1.0 . .
C C12 0.6431(3) 0.55365(18) 0.27092(16) 0.0273(5) Uani d . . . 1.0 . .
H H12A 0.6542 0.6208 0.2721 0.033 Uiso calc U . R 1.0 . .
H H12B 0.6269 0.5332 0.3297 0.033 Uiso calc U . R 1.0 . .
C C13 0.7420(4) 0.35998(17) 0.17422(18) 0.0332(6) Uani d . . . 1.0 . .
H H13A 0.7754 0.2954 0.1814 0.04 Uiso calc U . R 1.0 . .
H H13B 0.6226 0.362 0.1581 0.04 Uiso calc U . R 1.0 . .
C C14 0.7936(3) 0.41087(17) 0.26035(17) 0.0325(6) Uani d . . . 1.0 . .
H H14A 0.7196 0.3943 0.3016 0.039 Uiso calc U . R 1.0 . .
H H14B 0.9042 0.3913 0.2864 0.039 Uiso calc U . R 1.0 . .
C C15 0.9406(3) 0.55371(19) 0.29772(16) 0.0296(5) Uani d . . . 1.0 . .
H H15A 0.9623 0.5284 0.3577 0.036 Uiso calc U . R 1.0 . .
H H15B 0.9254 0.6203 0.3021 0.036 Uiso calc U . R 1.0 . .
C C16 1.0838(3) 0.5343(2) 0.25113(17) 0.0349(6) Uani d . . . 1.0 . .
H H16A 1.1799 0.5687 0.2795 0.042 Uiso calc U . R 1.0 . .
H H16B 1.1102 0.4686 0.255 0.042 Uiso calc U . R 1.0 . .
S S3 0.83646(7) 0.71562(4) -0.40956(4) 0.02620(18) Uani d U P D 0.952(2) A 1
O O1 0.7926(3) 0.81458(14) -0.42444(16) 0.0320(5) Uani d U P D 0.952(2) A 1
C C21 0.6576(7) 0.6594(3) -0.3890(3) 0.0431(8) Uani d U P D 0.952(2) A 1
H H21A 0.6802 0.5945 -0.3789 0.065 Uiso calc U P R 0.952(2) A 1
H H21B 0.6225 0.6861 -0.3372 0.065 Uiso calc U P R 0.952(2) A 1
H H21C 0.5716 0.6668 -0.4396 0.065 Uiso calc U P R 0.952(2) A 1
C C22 0.8418(5) 0.6704(2) -0.5155(2) 0.0493(9) Uani d U P D 0.952(2) A 1
H H22A 0.8699 0.6056 -0.5106 0.074 Uiso calc U P R 0.952(2) A 1
H H22B 0.7352 0.6776 -0.5518 0.074 Uiso calc U P R 0.952(2) A 1
H H22C 0.9233 0.7031 -0.5423 0.074 Uiso calc U P R 0.952(2) A 1
S S3A 0.7067(15) 0.7120(9) -0.4755(9) 0.029(4) Uani d U P D 0.048(2) A 2
O O1A 0.741(4) 0.8071(15) -0.443(3) 0.012(8) Uani d U P D 0.048(2) A 2
C C22A 0.896(5) 0.661(4) -0.481(5) 0.0493(9) Uani d U P D 0.048(2) A 2
H H22D 0.8791 0.598 -0.502 0.074 Uiso calc U P R 0.048(2) A 2
H H22E 0.952 0.6954 -0.5211 0.074 Uiso calc U P R 0.048(2) A 2
H H22F 0.9622 0.6604 -0.4225 0.074 Uiso calc U P R 0.048(2) A 2
C C21A 0.648(13) 0.647(5) -0.390(5) 0.0431(8) Uani d . P D 0.048(2) A 2
H H21D 0.6254 0.584 -0.4098 0.065 Uiso calc U P R 0.048(2) A 2
H H21E 0.7361 0.6466 -0.3395 0.065 Uiso calc U P R 0.048(2) A 2
H H21F 0.5507 0.6732 -0.3724 0.065 Uiso calc U P R 0.048(2) 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N4 . 2.0971(19) ?
Ni1 N5 . 2.102(2) ?
Ni1 N6 . 2.121(2) ?
Ni1 N3 . 2.122(2) ?
Ni1 S1 . 2.4080(6) ?
Ni1 S2 . 2.5260(6) ?
S1 C1 . 1.724(2) ?
S2 C1 . 1.711(2) ?
N1 C3 . 1.157(4) ?
N2 C4 . 1.146(4) ?
N3 C11 . 1.489(3) ?
N3 H3A . 0.88(3) ?
N3 H3B . 0.84(3) ?
N4 C12 . 1.477(3) ?
N4 C15 . 1.480(3) ?
N4 C14 . 1.496(3) ?
N5 C13 . 1.475(3) ?
N5 H5A . 0.82(3) ?
N5 H5B . 0.90(3) ?
N6 C16 . 1.478(3) ?
N6 H6A . 0.82(4) ?
N6 H6B . 0.92(4) ?
C1 C2 . 1.401(3) ?
C2 C3 . 1.416(4) ?
C2 C4 . 1.429(4) ?
C11 C12 . 1.522(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.529(4) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.523(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
S3 O1 . 1.507(2) ?
S3 C22 . 1.778(3) ?
S3 C21 . 1.783(4) ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
S3A O1A . 1.496(18) ?
S3A C22A . 1.769(17) ?
S3A C21A . 1.772(18) ?
C22A H22D . 0.98 ?
C22A H22E . 0.98 ?
C22A H22F . 0.98 ?
C21A H21D . 0.98 ?
C21A H21E . 0.98 ?
C21A H21F . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N4 Ni1 N5 . . 83.60(8) ?
N4 Ni1 N6 . . 83.19(8) ?
N5 Ni1 N6 . . 92.12(9) ?
N4 Ni1 N3 . . 81.75(8) ?
N5 Ni1 N3 . . 94.27(9) ?
N6 Ni1 N3 . . 162.87(8) ?
N4 Ni1 S1 . . 174.89(6) ?
N5 Ni1 S1 . . 101.34(6) ?
N6 Ni1 S1 . . 95.26(6) ?
N3 Ni1 S1 . . 99.03(6) ?
N4 Ni1 S2 . . 102.42(6) ?
N5 Ni1 S2 . . 173.98(6) ?
N6 Ni1 S2 . . 88.33(7) ?
N3 Ni1 S2 . . 86.98(6) ?
S1 Ni1 S2 . . 72.64(2) ?
C1 S1 Ni1 . . 86.96(8) ?
C1 S2 Ni1 . . 83.52(8) ?
C11 N3 Ni1 . . 110.87(15) ?
C11 N3 H3A . . 105.8(18) ?
Ni1 N3 H3A . . 103.8(18) ?
C11 N3 H3B . . 104.(2) ?
Ni1 N3 H3B . . 118.(2) ?
H3A N3 H3B . . 115.(3) ?
C12 N4 C15 . . 112.28(19) ?
C12 N4 C14 . . 111.98(19) ?
C15 N4 C14 . . 111.0(2) ?
C12 N4 Ni1 . . 105.38(14) ?
C15 N4 Ni1 . . 106.35(14) ?
C14 N4 Ni1 . . 109.54(15) ?
C13 N5 Ni1 . . 106.28(15) ?
C13 N5 H5A . . 111.(2) ?
Ni1 N5 H5A . . 108.(2) ?
C13 N5 H5B . . 106.2(19) ?
Ni1 N5 H5B . . 117.8(19) ?
H5A N5 H5B . . 107.(3) ?
C16 N6 Ni1 . . 109.04(15) ?
C16 N6 H6A . . 109.(2) ?
Ni1 N6 H6A . . 111.(2) ?
C16 N6 H6B . . 109.(2) ?
Ni1 N6 H6B . . 114.(2) ?
H6A N6 H6B . . 104.(3) ?
C2 C1 S2 . . 122.48(19) ?
C2 C1 S1 . . 120.84(18) ?
S2 C1 S1 . . 116.67(14) ?
C1 C2 C3 . . 121.3(2) ?
C1 C2 C4 . . 121.8(2) ?
C3 C2 C4 . . 116.8(2) ?
N1 C3 C2 . . 177.7(4) ?
N2 C4 C2 . . 178.9(3) ?
N3 C11 C12 . . 109.96(19) ?
N3 C11 H11A . . 109.7 ?
C12 C11 H11A . . 109.7 ?
N3 C11 H11B . . 109.7 ?
C12 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
N4 C12 C11 . . 110.09(19) ?
N4 C12 H12A . . 109.6 ?
C11 C12 H12A . . 109.6 ?
N4 C12 H12B . . 109.6 ?
C11 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.2 ?
N5 C13 C14 . . 110.2(2) ?
N5 C13 H13A . . 109.6 ?
C14 C13 H13A . . 109.6 ?
N5 C13 H13B . . 109.6 ?
C14 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
N4 C14 C13 . . 112.6(2) ?
N4 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
N4 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.8 ?
N4 C15 C16 . . 109.84(19) ?
N4 C15 H15A . . 109.7 ?
C16 C15 H15A . . 109.7 ?
N4 C15 H15B . . 109.7 ?
C16 C15 H15B . . 109.7 ?
H15A C15 H15B . . 108.2 ?
N6 C16 C15 . . 109.5(2) ?
N6 C16 H16A . . 109.8 ?
C15 C16 H16A . . 109.8 ?
N6 C16 H16B . . 109.8 ?
C15 C16 H16B . . 109.8 ?
H16A C16 H16B . . 108.2 ?
O1 S3 C22 . . 105.13(15) ?
O1 S3 C21 . . 106.44(18) ?
C22 S3 C21 . . 98.1(2) ?
S3 C21 H21A . . 109.5 ?
S3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
S3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
S3 C22 H22A . . 109.5 ?
S3 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
S3 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O1A S3A C22A . . 107.(2) ?
O1A S3A C21A . . 108.(3) ?
C22A S3A C21A . . 99.(2) ?
S3A C22A H22D . . 109.5 ?
S3A C22A H22E . . 109.5 ?
H22D C22A H22E . . 109.5 ?
S3A C22A H22F . . 109.5 ?
H22D C22A H22F . . 109.5 ?
H22E C22A H22F . . 109.5 ?
S3A C21A H21D . . 109.5 ?
S3A C21A H21E . . 109.5 ?
H21D C21A H21E . . 109.5 ?
S3A C21A H21F . . 109.5 ?
H21D C21A H21F . . 109.5 ?
H21E C21A H21F . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ni1 S2 C1 C2 . . . . -175.0(2) ?
Ni1 S2 C1 S1 . . . . 4.24(11) ?
Ni1 S1 C1 C2 . . . . 174.8(2) ?
Ni1 S1 C1 S2 . . . . -4.43(12) ?
S2 C1 C2 C3 . . . . 172.6(2) ?
S1 C1 C2 C3 . . . . -6.6(4) ?
S2 C1 C2 C4 . . . . -4.6(4) ?
S1 C1 C2 C4 . . . . 176.2(2) ?
Ni1 N3 C11 C12 . . . . 17.9(3) ?
C15 N4 C12 C11 . . . . 165.6(2) ?
C14 N4 C12 C11 . . . . -68.7(3) ?
Ni1 N4 C12 C11 . . . . 50.3(2) ?
N3 C11 C12 N4 . . . . -46.0(3) ?
Ni1 N5 C13 C14 . . . . -44.7(2) ?
C12 N4 C14 C13 . . . . 98.9(2) ?
C15 N4 C14 C13 . . . . -134.7(2) ?
Ni1 N4 C14 C13 . . . . -17.6(3) ?
N5 C13 C14 N4 . . . . 42.5(3) ?
C12 N4 C15 C16 . . . . -159.9(2) ?
C14 N4 C15 C16 . . . . 74.0(3) ?
Ni1 N4 C15 C16 . . . . -45.1(2) ?
Ni1 N6 C16 C15 . . . . -31.5(3) ?
N4 C15 C16 N6 . . . . 52.2(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O1 4_576 0.88(3) 2.21(3) 2.979(3) 146.(2) ?
N3 H3B S1 3_665 0.84(3) 2.67(3) 3.419(2) 150.(3) ?
N5 H5A S1 3_765 0.82(3) 2.93(3) 3.629(2) 145.(3) ?
N5 H5B O1 2_644 0.90(3) 2.18(3) 3.068(3) 168.(3) ?
N5 H5B S3A 2_644 0.90(3) 2.71(3) 3.416(13) 136.(2) ?
N5 H5B O1A 2_644 0.90(3) 1.98(5) 2.83(4) 157.(3) ?
N6 H6A O1 4_676 0.82(4) 2.60(3) 3.195(3) 130.(3) ?
N6 H6A O1A 4_676 0.82(4) 2.51(5) 3.13(3) 132.(3) ?
N6 H6B S1 3_765 0.92(4) 2.56(4) 3.445(2) 161.(3) ?


####################################################################### 
# 
# 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_dan9415
_database_code_depnum_ccdc_archive 'CCDC 2054291'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-03-16 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 N10 Ni2 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         604.13

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.3199(6)
_cell_length_b                   9.1021(3)
_cell_length_c                   18.1332(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.143(3)
_cell_angle_gamma                90
_cell_volume                     2457.99(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2872
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark orange'
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248

_exptl_absorpt_coefficient_mu    1.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            10388
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_theta_min         4.37
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_full        28.17
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_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.

The hydrogen atoms at N3, N4 and N5 were refined freely.
;

_reflns_number_total             2999
_reflns_number_gt                2344
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1148
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+12.9855P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni2 0.5 0.85978(7) 0.25 0.02073(16) Uani d T P S 1 . .
Ni Ni1 0.5 0.5 0 0.02568(18) Uani d . P S 1 . .
S S1 0.47903(6) 0.37137(10) 0.09440(6) 0.0291(2) Uani d . . . 1 . .
S S2 0.36043(6) 0.56121(12) -0.02367(6) 0.0331(2) Uani d . . . 1 . .
N N1 0.3242(2) 0.2014(4) 0.1817(2) 0.0418(9) Uani d . . . 1 . .
N N2 0.1408(2) 0.4883(4) -0.01320(19) 0.0364(8) Uani d . . . 1 . .
N N3 0.5310(2) 1.0182(4) 0.1823(2) 0.0255(6) Uani d . . . 1 . .
H H3A 0.481(3) 1.042(5) 0.142(3) 0.040(13) Uiso d . . . 1 . .
H H3B 0.552(4) 1.089(6) 0.212(3) 0.063(17) Uiso d . . . 1 . .
N N4 0.5505(2) 0.7135(4) 0.18644(18) 0.0273(7) Uani d . . . 1 . .
H H4 0.513(3) 0.647(4) 0.159(2) 0.026(10) Uiso d . . . 1 . .
N N5 0.6360(2) 0.8362(4) 0.3388(2) 0.0281(7) Uani d . . . 1 . .
H H5A 0.630(3) 0.806(6) 0.382(3) 0.051(15) Uiso d . . . 1 . .
H H5B 0.662(3) 0.912(5) 0.350(2) 0.026(11) Uiso d . . . 1 . .
C C1 0.3700(2) 0.4338(4) 0.0501(2) 0.0259(7) Uani d . . . 1 . .
C C2 0.3001(2) 0.3897(4) 0.0692(2) 0.0261(7) Uani d . . . 1 . .
C C3 0.3133(2) 0.2844(4) 0.1314(2) 0.0303(8) Uani d . . . 1 . .
C C4 0.2115(2) 0.4445(4) 0.0240(2) 0.0258(8) Uani d . . . 1 . .
C C11 0.5936(3) 0.9585(4) 0.1506(2) 0.0334(9) Uani d . . . 1 . .
H H11A 0.6557 0.9631 0.1928 0.04 Uiso calc U . R 1 . .
H H11B 0.5907 1.0174 0.1037 0.04 Uiso calc U . R 1 . .
C C12 0.5681(3) 0.7997(5) 0.1250(2) 0.0343(9) Uani d . . . 1 . .
H H12A 0.5137 0.7983 0.0736 0.041 Uiso calc U . R 1 . .
H H12B 0.6174 0.7525 0.1152 0.041 Uiso calc U . R 1 . .
C C13 0.6903(2) 0.7426(5) 0.3097(2) 0.0341(9) Uani d . . . 1 . .
H H13A 0.7348 0.6869 0.3554 0.041 Uiso calc U . R 1 . .
H H13B 0.7232 0.8047 0.2861 0.041 Uiso calc U . R 1 . .
C C14 0.6296(3) 0.6370(5) 0.2465(2) 0.0371(9) Uani d . . . 1 . .
H H14A 0.6637 0.5897 0.2186 0.045 Uiso calc U . R 1 . .
H H14B 0.6092 0.559 0.2732 0.045 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni2 N3 . 2.086(3) ?
Ni2 N3 2_655 2.086(3) ?
Ni2 N4 2_655 2.135(3) ?
Ni2 N4 . 2.135(3) ?
Ni2 N5 2_655 2.154(3) ?
Ni2 N5 . 2.154(3) ?
Ni1 S2 5_665 2.2098(10) ?
Ni1 S2 . 2.2098(10) ?
Ni1 S1 5_665 2.2129(10) ?
Ni1 S1 . 2.2130(10) ?
S1 C1 . 1.721(4) ?
S2 C1 . 1.729(4) ?
N1 C3 . 1.142(5) ?
N2 C4 . 1.145(5) ?
N3 C11 . 1.464(5) ?
N3 H3A . 0.87(5) ?
N3 H3B . 0.82(6) ?
N4 C14 . 1.478(5) ?
N4 C12 . 1.483(5) ?
N4 H4 . 0.86(4) ?
N5 C13 . 1.474(5) ?
N5 H5A . 0.87(5) ?
N5 H5B . 0.80(4) ?
C1 C2 . 1.381(5) ?
C2 C4 . 1.428(5) ?
C2 C3 . 1.428(5) ?
C11 C12 . 1.523(6) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.513(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Ni2 N3 . 2_655 92.57(19) ?
N3 Ni2 N4 . 2_655 171.53(13) ?
N3 Ni2 N4 2_655 2_655 82.70(13) ?
N3 Ni2 N4 . . 82.70(13) ?
N3 Ni2 N4 2_655 . 171.53(13) ?
N4 Ni2 N4 2_655 . 102.83(18) ?
N3 Ni2 N5 . 2_655 93.00(13) ?
N3 Ni2 N5 2_655 2_655 94.91(14) ?
N4 Ni2 N5 2_655 2_655 80.46(12) ?
N4 Ni2 N5 . 2_655 92.36(14) ?
N3 Ni2 N5 . . 94.91(14) ?
N3 Ni2 N5 2_655 . 93.00(13) ?
N4 Ni2 N5 2_655 . 92.36(14) ?
N4 Ni2 N5 . . 80.46(12) ?
N5 Ni2 N5 2_655 . 168.5(2) ?
S2 Ni1 S2 5_665 . 180.0 ?
S2 Ni1 S1 5_665 5_665 79.07(4) ?
S2 Ni1 S1 . 5_665 100.93(4) ?
S2 Ni1 S1 5_665 . 100.93(4) ?
S2 Ni1 S1 . . 79.07(4) ?
S1 Ni1 S1 5_665 . 180.0 ?
C1 S1 Ni1 . . 85.53(13) ?
C1 S2 Ni1 . . 85.44(13) ?
C11 N3 Ni2 . . 110.5(2) ?
C11 N3 H3A . . 109.(3) ?
Ni2 N3 H3A . . 107.(3) ?
C11 N3 H3B . . 112.(4) ?
Ni2 N3 H3B . . 108.(4) ?
H3A N3 H3B . . 111.(5) ?
C14 N4 C12 . . 115.1(3) ?
C14 N4 Ni2 . . 108.0(2) ?
C12 N4 Ni2 . . 108.1(2) ?
C14 N4 H4 . . 107.(3) ?
C12 N4 H4 . . 104.(3) ?
Ni2 N4 H4 . . 115.(3) ?
C13 N5 Ni2 . . 112.1(2) ?
C13 N5 H5A . . 117.(3) ?
Ni2 N5 H5A . . 104.(3) ?
C13 N5 H5B . . 105.(3) ?
Ni2 N5 H5B . . 113.(3) ?
H5A N5 H5B . . 107.(4) ?
C2 C1 S1 . . 126.2(3) ?
C2 C1 S2 . . 124.5(3) ?
S1 C1 S2 . . 109.4(2) ?
C1 C2 C4 . . 120.1(3) ?
C1 C2 C3 . . 121.3(3) ?
C4 C2 C3 . . 118.6(3) ?
N1 C3 C2 . . 179.3(5) ?
N2 C4 C2 . . 179.0(4) ?
N3 C11 C12 . . 108.9(3) ?
N3 C11 H11A . . 109.9 ?
C12 C11 H11A . . 109.9 ?
N3 C11 H11B . . 109.9 ?
C12 C11 H11B . . 109.9 ?
H11A C11 H11B . . 108.3 ?
N4 C12 C11 . . 112.7(3) ?
N4 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
N4 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
N5 C13 C14 . . 109.6(3) ?
N5 C13 H13A . . 109.8 ?
C14 C13 H13A . . 109.8 ?
N5 C13 H13B . . 109.8 ?
C14 C13 H13B . . 109.8 ?
H13A C13 H13B . . 108.2 ?
N4 C14 C13 . . 111.3(3) ?
N4 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
N4 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ni1 S1 C1 C2 . . . . 172.8(3) ?
Ni1 S1 C1 S2 . . . . -6.76(16) ?
Ni1 S2 C1 C2 . . . . -172.8(3) ?
Ni1 S2 C1 S1 . . . . 6.77(16) ?
S1 C1 C2 C4 . . . . -176.3(3) ?
S2 C1 C2 C4 . . . . 3.2(5) ?
S1 C1 C2 C3 . . . . 0.9(6) ?
S2 C1 C2 C3 . . . . -179.6(3) ?
Ni2 N3 C11 C12 . . . . 38.7(4) ?
C14 N4 C12 C11 . . . . -90.8(4) ?
Ni2 N4 C12 C11 . . . . 30.0(4) ?
N3 C11 C12 N4 . . . . -46.3(4) ?
Ni2 N5 C13 C14 . . . . -26.1(4) ?
C12 N4 C14 C13 . . . . 77.0(4) ?
Ni2 N4 C14 C13 . . . . -43.9(4) ?
N5 C13 C14 N4 . . . . 46.9(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A N2 7_565 0.87(5) 2.39(5) 3.198(5) 156.(4) ?
N3 H3B N1 2_665 0.82(6) 2.38(6) 3.111(5) 150.(5) ?
N4 H4 S1 . 0.86(4) 2.72(4) 3.500(3) 151.(3) ?


####################################################################### 
# 
# 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_dan9416
_database_code_depnum_ccdc_archive 'CCDC 2054292'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-03-16 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 N10 Ni2 O2 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         760.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.658(4)
_cell_length_b                   7.2167(14)
_cell_length_c                   14.534(3)
_cell_angle_alpha                90
_cell_angle_beta                 120.13(3)
_cell_angle_gamma                90
_cell_volume                     1692.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2091
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark orange'
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            7990
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_full        28.20
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_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.

One disordered over two positions DMF molecule was found in 
the asymmetrical unit. Several restraints (SADI, SAME, ISOR
and SIMU) were used in order to improve refinement stability.

The hydrogen atoms at N3 were refined freely, but with N-H
distance restraints (DFIX, SADI).
;

_reflns_number_total             2226
_reflns_number_gt                1856
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1261
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         2226
_refine_ls_number_parameters     150
_refine_ls_number_restraints     67
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+3.1459P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.439
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 1.0 -1.0 0.5 0.0370(2) Uani d T P S 1.0 . .
S S1 1.00844(6) -1.0 0.35349(8) 0.0421(3) Uani d T P S 1.0 . .
S S2 0.86801(6) -1.0 0.37772(8) 0.0471(3) Uani d T P S 1.0 . .
C C1 0.9027(2) -1.0 0.2882(3) 0.0390(8) Uani d T P S 1.0 . .
C C2 0.8513(2) -1.0 0.1775(3) 0.0393(8) Uani d T P S 1.0 . .
C C3 0.8878(2) -1.0 0.1129(3) 0.0375(8) Uani d T P S 1.0 . .
C C4 0.7632(3) -1.0 0.1284(3) 0.0460(10) Uani d T P S 1.0 . .
N N1 0.9206(2) -1.0 0.0641(3) 0.0418(7) Uani d T P S 1.0 . .
N N2 0.6923(2) -1.0 0.0902(3) 0.0586(10) Uani d T P S 1.0 . .
Ni Ni2 1.0 -1.0 0 0.0342(2) Uani d T P S 1.0 . .
N N3 1.07656(14) -0.8079(3) 0.11500(18) 0.0391(5) Uani d . . D 1.0 . .
H H3A 1.047(2) -0.720(4) 0.128(3) 0.070(11) Uiso d . . D 1.0 . .
H H3B 1.102(2) -0.745(5) 0.085(3) 0.063(10) Uiso d . . D 1.0 . .
C C11 1.13506(16) -0.9043(4) 0.2121(2) 0.0399(6) Uani d . . . 1.0 . .
C C12 1.18984(18) -0.8084(5) 0.3028(2) 0.0503(7) Uani d . . . 1.0 . .
H H12 1.1898 -0.6768 0.303 0.06 Uiso calc U . R 1.0 . .
C C13 1.2452(2) -0.9054(6) 0.3942(3) 0.0608(9) Uani d . . . 1.0 . .
H H13 1.2831 -0.8397 0.4566 0.073 Uiso calc U . R 1.0 . .
O O1 1.0027(2) -0.5 0.1713(3) 0.0636(10) Uani d TU P DS 1.0 A .
C C21 0.9437(4) -0.5 0.1841(5) 0.0646(13) Uani d TU P DS 1.0 . .
H H21 0.8891 -0.5 0.1245 0.078 Uiso calc U P R 0.626(15) A 1
H H21A 0.8946 -0.5 0.1164 0.078 Uiso calc U P R 0.374(15) A 2
N N4 0.9559(6) -0.5 0.2838(6) 0.048(2) Uani d TU P DS 0.626(15) A 1
C C22 1.0392(7) -0.5 0.3743(8) 0.075(3) Uani d TU P DS 0.626(15) A 1
H H22A 1.0368 -0.5 0.4402 0.112 Uiso calc U P R 0.626(15) A 1
H H22B 1.0686 -0.6109 0.3721 0.112 Uiso calc U P R 0.313(8) A 1
H H22C 1.0686 -0.3891 0.3721 0.112 Uiso calc U P R 0.313(8) A 1
C C23 0.8871(7) -0.5 0.3027(10) 0.071(3) Uani d TU P DS 0.626(15) A 1
H H23A 0.908 -0.5 0.3795 0.107 Uiso calc U P R 0.626(15) A 1
H H23B 0.8532 -0.3891 0.2707 0.107 Uiso calc U P R 0.313(8) A 1
H H23C 0.8532 -0.6109 0.2707 0.107 Uiso calc U P R 0.313(8) A 1
N N4A 0.9233(9) -0.5 0.2564(10) 0.049(3) Uani d TU P DS 0.374(15) A 2
C C22A 0.9863(16) -0.5 0.3653(13) 0.099(7) Uani d TU P DS 0.374(15) A 2
H H22D 0.9608 -0.5 0.4101 0.149 Uiso calc U P R 0.374(15) A 2
H H22E 1.0208 -0.6109 0.3805 0.149 Uiso calc U P R 0.187(8) A 2
H H22F 1.0208 -0.3891 0.3805 0.149 Uiso calc U P R 0.187(8) A 2
C C23A 0.8372(11) -0.5 0.221(2) 0.090(6) Uani d TU P DS 0.374(15) A 2
H H23D 0.8295 -0.5 0.2834 0.134 Uiso calc U P R 0.374(15) A 2
H H23E 0.8114 -0.3891 0.1785 0.134 Uiso calc U P R 0.187(8) A 2
H H23F 0.8114 -0.6109 0.1785 0.134 Uiso calc U P R 0.187(8) 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 S2 . 2.1974(14) ?
Ni1 S2 5_736 2.1974(14) ?
Ni1 S1 5_736 2.2125(10) ?
Ni1 S1 . 2.2125(10) ?
S1 C1 . 1.707(4) ?
S2 C1 . 1.719(4) ?
C1 C2 . 1.400(6) ?
C2 C3 . 1.409(5) ?
C2 C4 . 1.427(6) ?
C3 N1 . 1.145(5) ?
C4 N2 . 1.149(6) ?
N1 Ni2 . 2.110(3) ?
Ni2 N3 . 2.088(2) ?
Ni2 N3 5_735 2.088(2) ?
Ni2 N3 6_535 2.088(2) ?
Ni2 N3 2_755 2.088(2) ?
Ni2 N1 5_735 2.110(3) ?
N3 C11 . 1.456(4) ?
N3 H3A . 0.920(19) ?
N3 H3B . 0.916(18) ?
C11 C11 6_535 1.381(6) ?
C11 C12 . 1.382(4) ?
C12 C13 . 1.394(5) ?
C12 H12 . 0.95 ?
C13 C13 6_535 1.365(8) ?
C13 H13 . 0.95 ?
O1 C21 . 1.205(6) ?
C21 N4A . 1.285(11) ?
C21 N4 . 1.350(9) ?
C21 H21 . 0.95 ?
C21 H21A . 0.95 ?
N4 C23 . 1.441(9) ?
N4 C22 . 1.447(10) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
N4A C22A . 1.421(13) ?
N4A C23A . 1.421(13) ?
C22A H22D . 0.98 ?
C22A H22E . 0.98 ?
C22A H22F . 0.98 ?
C23A H23D . 0.98 ?
C23A H23E . 0.98 ?
C23A H23F . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S2 Ni1 S2 . 5_736 180.0 ?
S2 Ni1 S1 . 5_736 100.72(4) ?
S2 Ni1 S1 5_736 5_736 79.28(4) ?
S2 Ni1 S1 . . 79.28(4) ?
S2 Ni1 S1 5_736 . 100.72(4) ?
S1 Ni1 S1 5_736 . 180.0 ?
C1 S1 Ni1 . . 85.07(14) ?
C1 S2 Ni1 . . 85.25(14) ?
C2 C1 S1 . . 124.9(3) ?
C2 C1 S2 . . 124.7(3) ?
S1 C1 S2 . . 110.4(2) ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 C4 . . 121.8(3) ?
C3 C2 C4 . . 119.2(4) ?
N1 C3 C2 . . 177.2(4) ?
N2 C4 C2 . . 179.0(4) ?
C3 N1 Ni2 . . 170.1(3) ?
N3 Ni2 N3 . 5_735 180.0 ?
N3 Ni2 N3 . 6_535 83.21(13) ?
N3 Ni2 N3 5_735 6_535 96.79(13) ?
N3 Ni2 N3 . 2_755 96.79(13) ?
N3 Ni2 N3 5_735 2_755 83.21(13) ?
N3 Ni2 N3 6_535 2_755 180.00(10) ?
N3 Ni2 N1 . . 89.79(9) ?
N3 Ni2 N1 5_735 . 90.21(9) ?
N3 Ni2 N1 6_535 . 89.79(9) ?
N3 Ni2 N1 2_755 . 90.21(9) ?
N3 Ni2 N1 . 5_735 90.21(9) ?
N3 Ni2 N1 5_735 5_735 89.79(9) ?
N3 Ni2 N1 6_535 5_735 90.21(9) ?
N3 Ni2 N1 2_755 5_735 89.79(9) ?
N1 Ni2 N1 . 5_735 180.0 ?
C11 N3 Ni2 . . 109.70(18) ?
C11 N3 H3A . . 112.(2) ?
Ni2 N3 H3A . . 112.(2) ?
C11 N3 H3B . . 112.(2) ?
Ni2 N3 H3B . . 105.(2) ?
H3A N3 H3B . . 105.(3) ?
C11 C11 C12 6_535 . 120.06(19) ?
C11 C11 N3 6_535 . 118.56(15) ?
C12 C11 N3 . . 121.4(3) ?
C11 C12 C13 . . 119.8(3) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C13 C13 C12 6_535 . 120.1(2) ?
C13 C13 H13 6_535 . 119.9 ?
C12 C13 H13 . . 119.9 ?
O1 C21 N4A . . 142.6(9) ?
O1 C21 N4 . . 119.4(7) ?
O1 C21 H21 . . 120.3 ?
N4 C21 H21 . . 120.3 ?
O1 C21 H21A . . 108.7 ?
N4A C21 H21A . . 108.7 ?
C21 N4 C23 . . 121.2(7) ?
C21 N4 C22 . . 120.1(7) ?
C23 N4 C22 . . 118.7(8) ?
N4 C22 H22A . . 109.5 ?
N4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N4 C23 H23A . . 109.5 ?
N4 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
N4 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C21 N4A C22A . . 119.5(13) ?
C21 N4A C23A . . 117.0(13) ?
C22A N4A C23A . . 123.6(15) ?
N4A C22A H22D . . 109.5 ?
N4A C22A H22E . . 109.5 ?
H22D C22A H22E . . 109.5 ?
N4A C22A H22F . . 109.5 ?
H22D C22A H22F . . 109.5 ?
H22E C22A H22F . . 109.5 ?
N4A C23A H23D . . 109.5 ?
N4A C23A H23E . . 109.5 ?
H23D C23A H23E . . 109.5 ?
N4A C23A H23F . . 109.5 ?
H23D C23A H23F . . 109.5 ?
H23E C23A H23F . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ni1 S1 C1 C2 . . . . 180.0000(10) ?
Ni1 S1 C1 S2 . . . . 0 ?
Ni1 S2 C1 C2 . . . . 180.0000(10) ?
Ni1 S2 C1 S1 . . . . 0 ?
S1 C1 C2 C3 . . . . 0.0000(10) ?
S2 C1 C2 C3 . . . . 180.0000(10) ?
S1 C1 C2 C4 . . . . 180.0000(10) ?
S2 C1 C2 C4 . . . . 0.0000(10) ?
Ni2 N3 C11 C11 . . . 6_535 3.76(17) ?
Ni2 N3 C11 C12 . . . . -176.3(2) ?
C11 C11 C12 C13 6_535 . . . 0.2(3) ?
N3 C11 C12 C13 . . . . -179.7(3) ?
C11 C12 C13 C13 . . . 6_535 -0.2(3) ?
O1 C21 N4 C23 . . . . 180.000(2) ?
O1 C21 N4 C22 . . . . 0.0000(10) ?
O1 C21 N4A C22A . . . . 0.000(2) ?
O1 C21 N4A C23A . . . . 180.000(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O1 . 0.920(19) 2.03(2) 2.939(3) 169.(3) ?
N3 H3B N2 3 0.916(18) 2.41(2) 3.242(4) 151.(3) ?



#=============================================================================
#  end of cif data for "dan9416" (compound 3)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
