# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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).
# 
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# 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 
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data_dubr29
_database_code_depnum_ccdc_archive 'CCDC 1813281'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_audit_creation_date             2018-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 I N2 Ni S2'
_chemical_formula_sum            'C20 H25 I N2 Ni S2'
_chemical_formula_weight         543.15
_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 0.0150 0.0070 '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'
I I 0.0970 5.4980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3410 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5090(9)
_cell_length_b                   13.1454(7)
_cell_length_c                   14.0524(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.914(5)
_cell_angle_gamma                90
_cell_volume                     2282.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    100
_cell_measurement_theta_max      54.37
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   0.624
_shelx_estimated_absorpt_T_min   0.304
_exptl_absorpt_coefficient_mu    13.006
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.3549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1394 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.4727.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9768
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.052
_diffrn_reflns_theta_min         3.111
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             4275
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         3.511
_refine_diff_density_min         -3.555
_refine_diff_density_rms         0.354
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1777
_refine_ls_R_factor_gt           0.0924
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2394
_refine_ls_wR_factor_ref         0.3285
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1 I 0.76031(10) 0.47384(6) 0.81658(6) 0.0441(4) Uani 1 1 d . . . . .
Ni1 Ni 0.6940(2) 0.63485(13) 0.72754(13) 0.0390(7) Uani 1 1 d . . . . .
S1 S 0.5794(4) 0.6632(2) 0.8251(2) 0.0409(11) Uani 1 1 d . . . . .
S2 S 0.8009(4) 0.6160(3) 0.6210(3) 0.0486(12) Uani 1 1 d . . . . .
N1 N 0.4590(12) 0.8300(9) 0.8310(8) 0.042(3) Uani 1 1 d . . . . .
N2 N 0.8120(13) 0.7433(10) 0.4756(8) 0.048(4) Uani 1 1 d . . . . .
C1 C 0.6526(14) 0.7593(10) 0.6694(10) 0.038(4) Uani 1 1 d . . . . .
C2 C 0.5757(15) 0.8229(10) 0.7076(10) 0.046(5) Uani 1 1 d . . . . .
C3 C 0.5571(13) 0.9215(10) 0.6680(10) 0.038(4) Uani 1 1 d . . . . .
H3 H 0.5081 0.9646 0.6941 0.046 Uiso 1 1 calc R . . . .
C4 C 0.6045(16) 0.9574(10) 0.5962(11) 0.049(5) Uani 1 1 d . . . . .
H4 H 0.5900 1.0245 0.5725 0.059 Uiso 1 1 calc R . . . .
C5 C 0.6753(15) 0.8949(11) 0.5569(11) 0.045(4) Uani 1 1 d . . . . .
H5 H 0.7082 0.9199 0.5050 0.054 Uiso 1 1 calc R . . . .
C6 C 0.7001(16) 0.7968(11) 0.5906(10) 0.050(5) Uani 1 1 d . . . . .
C7 C 0.5325(15) 0.7813(10) 0.7884(10) 0.043(4) Uani 1 1 d . . . . .
C8 C 0.4115(16) 0.7910(11) 0.9139(10) 0.051(5) Uani 1 1 d . . . . .
H8 H 0.4613 0.7377 0.9464 0.061 Uiso 1 1 calc R . . . .
C9 C 0.3017(15) 0.7407(12) 0.8800(12) 0.052(5) Uani 1 1 d . . . . .
H9A H 0.2525 0.7898 0.8420 0.062 Uiso 1 1 calc R . . . .
H9B H 0.3111 0.6816 0.8384 0.062 Uiso 1 1 calc R . . . .
C10 C 0.253(2) 0.7061(14) 0.9665(13) 0.084(8) Uani 1 1 d . . . . .
H10A H 0.2985 0.6510 1.0000 0.100 Uiso 1 1 calc R . . . .
H10B H 0.1800 0.6786 0.9451 0.100 Uiso 1 1 calc R . . . .
C11 C 0.2472(18) 0.7952(13) 1.0364(13) 0.066(6) Uani 1 1 d . . . . .
H11A H 0.1988 0.8481 1.0033 0.079 Uiso 1 1 calc R . . . .
H11B H 0.2147 0.7706 1.0920 0.079 Uiso 1 1 calc R . . . .
C12 C 0.3529(19) 0.8411(13) 1.0720(11) 0.063(6) Uani 1 1 d . . . . .
H12A H 0.4000 0.7907 1.1104 0.075 Uiso 1 1 calc R . . . .
H12B H 0.3434 0.8999 1.1139 0.075 Uiso 1 1 calc R . . . .
C13 C 0.4059(19) 0.8765(14) 0.9855(11) 0.069(7) Uani 1 1 d . . . . .
H13A H 0.3637 0.9337 0.9528 0.083 Uiso 1 1 calc R . . . .
H13B H 0.4800 0.9014 1.0091 0.083 Uiso 1 1 calc R . . . .
C14 C 0.7725(15) 0.7246(11) 0.5538(10) 0.045(5) Uani 1 1 d . . . . .
C15 C 0.8823(15) 0.6696(12) 0.4289(11) 0.047(4) Uani 1 1 d . . . . .
H15 H 0.9374 0.6389 0.4800 0.057 Uiso 1 1 calc R . . . .
C16 C 0.939(2) 0.7290(15) 0.3603(13) 0.074(7) Uani 1 1 d . . . . .
H16A H 0.9852 0.7821 0.3960 0.089 Uiso 1 1 calc R . . . .
H16B H 0.8851 0.7631 0.3118 0.089 Uiso 1 1 calc R . . . .
C17 C 1.0095(16) 0.6569(15) 0.3096(13) 0.060(5) Uani 1 1 d . . . . .
H17A H 1.0675 0.6279 0.3579 0.072 Uiso 1 1 calc R . . . .
H17B H 1.0441 0.6960 0.2625 0.072 Uiso 1 1 calc R . . . .
C18 C 0.9415(17) 0.5697(19) 0.2571(13) 0.069(6) Uani 1 1 d . . . . .
H18A H 0.9894 0.5214 0.2299 0.083 Uiso 1 1 calc R . . . .
H18B H 0.8890 0.5976 0.2035 0.083 Uiso 1 1 calc R . . . .
C19 C 0.880(2) 0.5137(15) 0.3292(14) 0.073(7) Uani 1 1 d . . . . .
H19A H 0.8344 0.4600 0.2947 0.087 Uiso 1 1 calc R . . . .
H19B H 0.9337 0.4802 0.3789 0.087 Uiso 1 1 calc R . . . .
C20 C 0.8107(19) 0.5844(14) 0.3778(14) 0.072(6) Uani 1 1 d . . . . .
H20A H 0.7757 0.5462 0.4253 0.086 Uiso 1 1 calc R . . . .
H20B H 0.7534 0.6141 0.3293 0.086 Uiso 1 1 calc R . . . .


_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
I1 Ni1 2.5321(19) . ?
Ni1 S1 2.163(5) . ?
Ni1 S2 2.171(5) . ?
Ni1 C1 1.866(14) . ?
S1 C7 1.712(13) . ?
S2 C14 1.719(15) . ?
N1 C7 1.33(2) . ?
N1 C8 1.48(2) . ?
N2 C14 1.30(2) . ?
N2 C15 1.52(2) . ?
C1 C2 1.44(2) . ?
C1 C6 1.42(2) . ?
C2 C3 1.415(17) . ?
C2 C7 1.44(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.33(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.38(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.39(2) . ?
C6 C14 1.46(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.53(3) . ?
C8 C13 1.52(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.51(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.54(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.47(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.54(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15 1.0000 . ?
C15 C16 1.50(3) . ?
C15 C20 1.54(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.54(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.55(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.55(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.51(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
S1 Ni1 I1 91.68(11) . . ?
S1 Ni1 S2 174.94(16) . . ?
S2 Ni1 I1 93.17(12) . . ?
C1 Ni1 I1 175.4(4) . . ?
C1 Ni1 S1 87.7(5) . . ?
C1 Ni1 S2 87.5(5) . . ?
C7 S1 Ni1 101.3(6) . . ?
C14 S2 Ni1 100.8(7) . . ?
C7 N1 C8 125.2(12) . . ?
C14 N2 C15 124.5(13) . . ?
C2 C1 Ni1 120.1(11) . . ?
C6 C1 Ni1 121.6(12) . . ?
C6 C1 C2 118.2(13) . . ?
C3 C2 C1 117.6(16) . . ?
C3 C2 C7 126.8(16) . . ?
C7 C2 C1 115.4(12) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 C2 123.8(16) . . ?
C4 C3 H3 118.1 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(14) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.5(17) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C14 114.0(13) . . ?
C5 C6 C1 119.2(17) . . ?
C5 C6 C14 126.8(17) . . ?
N1 C7 S1 121.8(12) . . ?
N1 C7 C2 122.8(13) . . ?
C2 C7 S1 115.4(12) . . ?
N1 C8 H8 107.7 . . ?
N1 C8 C9 110.9(12) . . ?
N1 C8 C13 109.3(14) . . ?
C9 C8 H8 107.7 . . ?
C13 C8 H8 107.7 . . ?
C13 C8 C9 113.2(17) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 C8 109.4(16) . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 C11 110.5(16) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.5(18) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C11 C12 C13 109.3(14) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C8 C13 C12 111.6(16) . . ?
C8 C13 H13A 109.3 . . ?
C8 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 S2 123.3(14) . . ?
N2 C14 C6 121.1(14) . . ?
C6 C14 S2 115.6(12) . . ?
N2 C15 H15 109.1 . . ?
N2 C15 C20 109.3(16) . . ?
C16 C15 N2 107.9(14) . . ?
C16 C15 H15 109.1 . . ?
C16 C15 C20 112.2(16) . . ?
C20 C15 H15 109.1 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C15 C16 C17 109.7(15) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C16 C17 C18 111.4(17) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
C17 C18 C19 109.4(15) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 C18 112.5(18) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C15 C20 H20A 109.9 . . ?
C15 C20 H20B 109.9 . . ?
C19 C20 C15 108.9(19) . . ?
C19 C20 H20A 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 S1 C7 N1 -179.2(12) . . . . ?
Ni1 S1 C7 C2 2.2(12) . . . . ?
Ni1 S2 C14 N2 -174.4(13) . . . . ?
Ni1 S2 C14 C6 5.8(13) . . . . ?
Ni1 C1 C2 C3 172.6(10) . . . . ?
Ni1 C1 C2 C7 -2.4(18) . . . . ?
Ni1 C1 C6 C5 -172.9(11) . . . . ?
Ni1 C1 C6 C14 6.8(19) . . . . ?
S1 Ni1 C1 C2 3.1(11) . . . . ?
S1 Ni1 C1 C6 179.4(12) . . . . ?
S2 Ni1 C1 C2 -178.7(12) . . . . ?
S2 Ni1 C1 C6 -2.5(12) . . . . ?
N1 C8 C9 C10 -177.5(13) . . . . ?
N1 C8 C13 C12 177.9(15) . . . . ?
N2 C15 C16 C17 -178.8(14) . . . . ?
N2 C15 C20 C19 178.2(14) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C1 C2 C7 S1 -0.3(17) . . . . ?
C1 C2 C7 N1 -178.9(14) . . . . ?
C1 C6 C14 S2 -8.2(19) . . . . ?
C1 C6 C14 N2 172.1(14) . . . . ?
C2 C1 C6 C5 3(2) . . . . ?
C2 C1 C6 C14 -176.9(13) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C2 C7 S1 -174.7(12) . . . . ?
C3 C2 C7 N1 7(2) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C4 C5 C6 C1 -1(2) . . . . ?
C4 C5 C6 C14 179.3(15) . . . . ?
C5 C6 C14 S2 171.4(13) . . . . ?
C5 C6 C14 N2 -8(3) . . . . ?
C6 C1 C2 C3 -4(2) . . . . ?
C6 C1 C2 C7 -178.8(13) . . . . ?
C7 N1 C8 C9 -97.2(17) . . . . ?
C7 N1 C8 C13 137.3(16) . . . . ?
C7 C2 C3 C4 176.1(15) . . . . ?
C8 N1 C7 S1 1(2) . . . . ?
C8 N1 C7 C2 179.7(14) . . . . ?
C8 C9 C10 C11 55(2) . . . . ?
C9 C8 C13 C12 53.7(18) . . . . ?
C9 C10 C11 C12 -59(2) . . . . ?
C10 C11 C12 C13 56.7(17) . . . . ?
C11 C12 C13 C8 -53.6(19) . . . . ?
C13 C8 C9 C10 -54.2(17) . . . . ?
C14 N2 C15 C16 -162.6(16) . . . . ?
C14 N2 C15 C20 75(2) . . . . ?
C15 N2 C14 S2 4(2) . . . . ?
C15 N2 C14 C6 -176.0(14) . . . . ?
C15 C16 C17 C18 57(2) . . . . ?
C16 C15 C20 C19 59(2) . . . . ?
C16 C17 C18 C19 -55(2) . . . . ?
C17 C18 C19 C20 56(2) . . . . ?
C18 C19 C20 C15 -57(2) . . . . ?
C20 C15 C16 C17 -58(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dubr24
_database_code_depnum_ccdc_archive 'CCDC 1813283'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_audit_creation_date             2018-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 I N2 Ni S2'
_chemical_formula_sum            'C16 H19 I N2 Ni S2'
_chemical_formula_weight         489.06
_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 0.0150 0.0070 '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'
I I 0.0970 5.4980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3410 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.5312(3)
_cell_length_b                   12.1900(3)
_cell_length_c                   22.2460(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3398.20(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7445
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.938
_cell_measurement_theta_min      3.069
_shelx_estimated_absorpt_T_max   0.275
_shelx_estimated_absorpt_T_min   0.078
_exptl_absorpt_coefficient_mu    17.419
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.2062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.1220 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.2747. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10813
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.015
_diffrn_reflns_theta_min         3.457
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2684
_reflns_number_total             2976
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.242
_refine_diff_density_min         -1.798
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.022
_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)+(0.0811P)²+6.7391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1218
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C12(H12A,H12B), C9(H9A,H9B), C14(H14A,H14B), C11(H11A,H11B),
 C16(H16A,H16B), C13(H13A,H13B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1 I 0.58582(2) 0.32546(2) 0.34911(2) 0.01500(16) Uani 1 1 d . U . . .
Ni1 Ni 0.38648(5) 0.32081(5) 0.37459(3) 0.0101(2) Uani 1 1 d . U . . .
S2 S 0.40431(9) 0.17608(9) 0.42859(5) 0.0136(3) Uani 1 1 d . U . . .
S1 S 0.35782(8) 0.46987(9) 0.32612(5) 0.0140(3) Uani 1 1 d . U . . .
N1 N 0.1749(3) 0.5454(3) 0.28734(15) 0.0115(7) Uani 1 1 d . U . . .
C1 C 0.2387(4) 0.3094(3) 0.38580(18) 0.0112(9) Uani 1 1 d . U . . .
C2 C 0.1673(3) 0.3853(4) 0.35806(17) 0.0115(9) Uani 1 1 d . U . . .
N2 N 0.2549(3) 0.0649(3) 0.48414(16) 0.0131(8) Uani 1 1 d . U . . .
C8 C 0.2741(3) 0.1487(4) 0.44814(18) 0.0112(8) Uani 1 1 d . U . . .
C6 C 0.1937(3) 0.2245(4) 0.42198(18) 0.0118(8) Uani 1 1 d . U . . .
C7 C 0.2213(3) 0.4710(4) 0.32240(18) 0.0118(9) Uani 1 1 d . U . . .
C4 C 0.0157(4) 0.2957(4) 0.40475(18) 0.0158(9) Uani 1 1 d . U . . .
H4 H -0.0590 0.2913 0.4115 0.019 Uiso 1 1 calc R . . . .
C15 C 0.2894(4) -0.0505(4) 0.56690(19) 0.0176(10) Uani 1 1 d . U . . .
H15A H 0.2858 0.0019 0.6008 0.021 Uiso 1 1 calc R . . . .
H15B H 0.3278 -0.1173 0.5801 0.021 Uiso 1 1 calc R . . . .
C12 C 0.2399(3) 0.6268(4) 0.2540(2) 0.0144(9) Uani 1 1 d . U . . .
H12A H 0.2823 0.5908 0.2220 0.017 Uiso 1 1 calc R . . . .
H12B H 0.2889 0.6662 0.2814 0.017 Uiso 1 1 calc R . . . .
C3 C 0.0567(4) 0.3790(4) 0.36912(19) 0.0134(9) Uani 1 1 d . U . . .
H3 H 0.0101 0.4321 0.3521 0.016 Uiso 1 1 calc R . . . .
C9 C 0.0603(3) 0.5578(4) 0.27238(19) 0.0118(9) Uani 1 1 d . U . . .
H9A H 0.0205 0.5911 0.3062 0.014 Uiso 1 1 calc R . . . .
H9B H 0.0278 0.4860 0.2625 0.014 Uiso 1 1 calc R . . . .
C14 C 0.1779(4) -0.0783(4) 0.54340(19) 0.0163(9) Uani 1 1 d . U . . .
H14A H 0.1788 -0.1475 0.5200 0.020 Uiso 1 1 calc R . . . .
H14B H 0.1264 -0.0857 0.5769 0.020 Uiso 1 1 calc R . . . .
C11 C 0.1581(3) 0.7047(4) 0.2272(2) 0.0165(9) Uani 1 1 d . U . . .
H11A H 0.1425 0.7658 0.2551 0.020 Uiso 1 1 calc R . . . .
H11B H 0.1837 0.7353 0.1885 0.020 Uiso 1 1 calc R . . . .
C16 C 0.3427(4) 0.0009(4) 0.51252(18) 0.0154(9) Uani 1 1 d . U . . .
H16A H 0.4023 0.0494 0.5247 0.018 Uiso 1 1 calc R . . . .
H16B H 0.3702 -0.0561 0.4848 0.018 Uiso 1 1 calc R . . . .
C13 C 0.1495(3) 0.0192(4) 0.5033(2) 0.0142(9) Uani 1 1 d . U . . .
H13A H 0.1074 -0.0049 0.4680 0.017 Uiso 1 1 calc R . . . .
H13B H 0.1079 0.0746 0.5259 0.017 Uiso 1 1 calc R . . . .
C10 C 0.0603(4) 0.6335(4) 0.2177(2) 0.0178(10) Uani 1 1 d . U . . .
H10A H 0.0660 0.5910 0.1800 0.021 Uiso 1 1 calc R . . . .
H10B H -0.0054 0.6786 0.2164 0.021 Uiso 1 1 calc R . . . .
C5 C 0.0827(3) 0.2191(4) 0.4305(2) 0.0136(9) Uani 1 1 d . U . . .
H5 H 0.0534 0.1620 0.4544 0.016 Uiso 1 1 calc R . . . .


_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
I1 Ni1 2.5620(7) . ?
Ni1 S2 2.1462(13) . ?
Ni1 S1 2.1431(12) . ?
Ni1 C1 1.874(5) . ?
S2 C8 1.722(4) . ?
S1 C7 1.713(4) . ?
N1 C7 1.329(6) . ?
N1 C12 1.483(5) . ?
N1 C9 1.483(5) . ?
C1 C2 1.428(6) . ?
C1 C6 1.427(6) . ?
C2 C7 1.476(6) . ?
C2 C3 1.410(6) . ?
N2 C8 1.320(6) . ?
N2 C16 1.489(5) . ?
N2 C13 1.495(5) . ?
C8 C6 1.485(6) . ?
C6 C5 1.405(6) . ?
C4 C3 1.387(6) . ?
C4 C5 1.381(6) . ?
C15 C14 1.530(6) . ?
C15 C16 1.517(6) . ?
C12 C11 1.519(6) . ?
C9 C10 1.527(6) . ?
C14 C13 1.529(6) . ?
C11 C10 1.516(6) . ?

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
S2 Ni1 I1 92.32(4) . . ?
S1 Ni1 I1 91.91(4) . . ?
S1 Ni1 S2 174.90(5) . . ?
C1 Ni1 I1 174.08(13) . . ?
C1 Ni1 S2 88.12(14) . . ?
C1 Ni1 S1 87.96(14) . . ?
C8 S2 Ni1 101.66(16) . . ?
C7 S1 Ni1 101.46(15) . . ?
C7 N1 C12 120.6(4) . . ?
C7 N1 C9 128.7(4) . . ?
C9 N1 C12 110.6(3) . . ?
C2 C1 Ni1 120.9(3) . . ?
C6 C1 Ni1 121.3(3) . . ?
C6 C1 C2 117.8(4) . . ?
C1 C2 C7 113.8(4) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 C7 125.6(4) . . ?
C8 N2 C16 121.9(4) . . ?
C8 N2 C13 128.4(4) . . ?
C16 N2 C13 109.7(3) . . ?
N2 C8 S2 118.4(3) . . ?
N2 C8 C6 126.6(4) . . ?
C6 C8 S2 115.0(3) . . ?
C1 C6 C8 113.9(4) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 C8 126.1(4) . . ?
N1 C7 S1 118.1(3) . . ?
N1 C7 C2 126.7(4) . . ?
C2 C7 S1 115.2(3) . . ?
C5 C4 C3 120.5(4) . . ?
C16 C15 C14 102.8(3) . . ?
N1 C12 C11 104.2(3) . . ?
C4 C3 C2 120.2(4) . . ?
N1 C9 C10 103.9(3) . . ?
C13 C14 C15 103.9(4) . . ?
C10 C11 C12 104.0(4) . . ?
N2 C16 C15 103.3(3) . . ?
N2 C13 C14 104.5(3) . . ?
C11 C10 C9 103.7(3) . . ?
C4 C5 C6 120.9(4) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 S2 C8 N2 -177.6(3) . . . . ?
Ni1 S2 C8 C6 2.2(3) . . . . ?
Ni1 S1 C7 N1 -170.5(3) . . . . ?
Ni1 S1 C7 C2 7.8(3) . . . . ?
Ni1 C1 C2 C7 -1.3(5) . . . . ?
Ni1 C1 C2 C3 -177.0(3) . . . . ?
Ni1 C1 C6 C8 -0.6(5) . . . . ?
Ni1 C1 C6 C5 178.8(3) . . . . ?
S2 Ni1 C1 C2 -178.0(3) . . . . ?
S2 Ni1 C1 C6 1.6(3) . . . . ?
S2 C8 C6 C1 -1.3(5) . . . . ?
S2 C8 C6 C5 179.4(4) . . . . ?
S1 Ni1 C1 C2 5.2(3) . . . . ?
S1 Ni1 C1 C6 -175.1(3) . . . . ?
N1 C12 C11 C10 -29.7(4) . . . . ?
N1 C9 C10 C11 -30.5(4) . . . . ?
C1 C2 C7 S1 -5.1(5) . . . . ?
C1 C2 C7 N1 173.1(4) . . . . ?
C1 C2 C3 C4 -3.1(6) . . . . ?
C1 C6 C5 C4 -0.5(6) . . . . ?
C2 C1 C6 C8 179.1(3) . . . . ?
C2 C1 C6 C5 -1.5(6) . . . . ?
N2 C8 C6 C1 178.5(4) . . . . ?
N2 C8 C6 C5 -0.8(7) . . . . ?
C8 N2 C16 C15 157.3(4) . . . . ?
C8 N2 C13 C14 178.6(4) . . . . ?
C8 C6 C5 C4 178.7(4) . . . . ?
C6 C1 C2 C7 179.1(4) . . . . ?
C6 C1 C2 C3 3.3(6) . . . . ?
C7 N1 C12 C11 -172.4(4) . . . . ?
C7 N1 C9 C10 -164.2(4) . . . . ?
C7 C2 C3 C4 -178.3(4) . . . . ?
C15 C14 C13 N2 25.0(4) . . . . ?
C12 N1 C7 S1 -1.8(5) . . . . ?
C12 N1 C7 C2 -179.9(4) . . . . ?
C12 N1 C9 C10 12.3(4) . . . . ?
C12 C11 C10 C9 37.5(5) . . . . ?
C3 C2 C7 S1 170.4(3) . . . . ?
C3 C2 C7 N1 -11.5(7) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C9 N1 C7 S1 174.4(3) . . . . ?
C9 N1 C7 C2 -3.7(7) . . . . ?
C9 N1 C12 C11 10.8(5) . . . . ?
C14 C15 C16 N2 37.4(4) . . . . ?
C16 N2 C8 S2 5.9(5) . . . . ?
C16 N2 C8 C6 -173.9(4) . . . . ?
C16 N2 C13 C14 -1.6(4) . . . . ?
C16 C15 C14 C13 -38.9(5) . . . . ?
C13 N2 C8 S2 -174.4(3) . . . . ?
C13 N2 C8 C6 5.8(7) . . . . ?
C13 N2 C16 C15 -22.5(4) . . . . ?
C5 C4 C3 C2 1.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dubr32
_database_code_depnum_ccdc_archive 'CCDC 1813282'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_audit_creation_date             2018-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 I N2 Ni S2'
_chemical_formula_sum            'C18 H23 I N2 Ni S2'
_chemical_formula_weight         517.11
_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 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3410 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I 0.0970 5.4980 '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                   9.0954(12)
_cell_length_b                   10.4357(13)
_cell_length_c                   11.0814(14)
_cell_angle_alpha                64.612(4)
_cell_angle_beta                 89.389(6)
_cell_angle_gamma                87.803(6)
_cell_volume                     949.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.641
_cell_measurement_theta_min      3.842
_shelx_estimated_absorpt_T_max   0.574
_shelx_estimated_absorpt_T_min   0.256
_exptl_absorpt_coefficient_mu    15.610
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.3802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1592 before and 0.1126 after correction. The Ratio of minimum to maximum transmission is 0.5057. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21575
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.061
_diffrn_reflns_theta_min         3.841
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3637
_reflns_number_total             4348
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         2.273
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.230
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.112
_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)+(0.0985P)²+2.3201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.1964(8) 0.6917(6) 0.5464(6) 0.0475(14) Uani 1 1 d . . . . .
C2 C 0.1895(8) 0.6904(7) 0.4196(6) 0.0487(14) Uani 1 1 d . . . . .
C3 C 0.1470(8) 0.8137(7) 0.3068(7) 0.0504(14) Uani 1 1 d . . . . .
H3 H 0.1321 0.8096 0.2238 0.060 Uiso 1 1 calc R . . . .
C4 C 0.1262(8) 0.9429(7) 0.3157(7) 0.0519(15) Uani 1 1 d . . . . .
H4 H 0.0959 1.0264 0.2395 0.062 Uiso 1 1 calc R . . . .
C5 C 0.1502(8) 0.9477(7) 0.4356(7) 0.0506(14) Uani 1 1 d . . . . .
H5 H 0.1404 1.0363 0.4405 0.061 Uiso 1 1 calc R . . . .
C6 C 0.1889(8) 0.8255(6) 0.5511(6) 0.0486(14) Uani 1 1 d . . . . .
C7 C 0.2022(7) 0.5471(6) 0.4235(6) 0.0468(13) Uani 1 1 d . . . . .
C9 C 0.2983(9) 0.6252(7) 0.1930(7) 0.0537(15) Uani 1 1 d . . . . .
H9A H 0.3193 0.7137 0.2008 0.064 Uiso 1 1 calc R . . . .
H9B H 0.2315 0.6495 0.1157 0.064 Uiso 1 1 calc R . . . .
C10 C 0.4388(9) 0.5577(8) 0.1720(8) 0.0598(17) Uani 1 1 d . . . . .
H10A H 0.5075 0.5401 0.2466 0.072 Uiso 1 1 calc R . . . .
H10B H 0.4852 0.6240 0.0883 0.072 Uiso 1 1 calc R . . . .
C11 C 0.4131(9) 0.4172(8) 0.1638(7) 0.0573(16) Uani 1 1 d . . . . .
H11A H 0.3492 0.4343 0.0862 0.069 Uiso 1 1 calc R . . . .
H11B H 0.5081 0.3742 0.1523 0.069 Uiso 1 1 calc R . . . .
C12 C 0.3403(9) 0.3179(8) 0.2917(8) 0.0582(16) Uani 1 1 d . . . . .
H12A H 0.3172 0.2288 0.2859 0.070 Uiso 1 1 calc R . . . .
H12B H 0.4086 0.2939 0.3680 0.070 Uiso 1 1 calc R . . . .
C13 C 0.2008(8) 0.3870(7) 0.3146(7) 0.0531(15) Uani 1 1 d . . . . .
H13A H 0.1291 0.4017 0.2428 0.064 Uiso 1 1 calc R . . . .
H13B H 0.1573 0.3228 0.4007 0.064 Uiso 1 1 calc R . . . .
C8 C 0.2035(7) 0.8180(7) 0.6856(7) 0.0487(14) Uani 1 1 d . . . . .
C14 C 0.3164(8) 1.0522(7) 0.6125(7) 0.0547(16) Uani 1 1 d . . . . .
H14A H 0.2590 1.1403 0.5977 0.066 Uiso 1 1 calc R . . . .
H14B H 0.3262 1.0467 0.5258 0.066 Uiso 1 1 calc R . . . .
C15 C 0.4680(9) 1.0555(9) 0.6673(8) 0.0640(18) Uani 1 1 d . . . . .
H15A H 0.5280 0.9719 0.6732 0.077 Uiso 1 1 calc R . . . .
H15B H 0.5174 1.1417 0.6049 0.077 Uiso 1 1 calc R . . . .
C16 C 0.4601(10) 1.0552(9) 0.8020(8) 0.068(2) Uani 1 1 d . . . . .
H16A H 0.4119 1.1450 0.7944 0.081 Uiso 1 1 calc R . . . .
H16B H 0.5609 1.0489 0.8375 0.081 Uiso 1 1 calc R . . . .
C17 C 0.3735(10) 0.9300(9) 0.8979(8) 0.070(2) Uani 1 1 d . . . . .
H17A H 0.4291 0.8402 0.9154 0.084 Uiso 1 1 calc R . . . .
H17B H 0.3612 0.9367 0.9839 0.084 Uiso 1 1 calc R . . . .
C18 C 0.2246(9) 0.9284(8) 0.8406(7) 0.0586(17) Uani 1 1 d . . . . .
H18A H 0.1731 0.8430 0.9017 0.070 Uiso 1 1 calc R . . . .
H18B H 0.1649 1.0131 0.8325 0.070 Uiso 1 1 calc R . . . .
N1 N 0.2273(6) 0.5248(6) 0.3167(5) 0.0493(12) Uani 1 1 d . . . . .
N2 N 0.2392(7) 0.9279(6) 0.7082(5) 0.0511(12) Uani 1 1 d . . . . .
S1 S 0.1848(2) 0.41123(16) 0.58012(16) 0.0515(4) Uani 1 1 d . . . . .
S2 S 0.1712(2) 0.65473(16) 0.81413(16) 0.0509(4) Uani 1 1 d . . . . .
Ni1 Ni 0.18023(10) 0.52356(9) 0.70511(8) 0.0455(2) Uani 1 1 d . . . . .
I1 I 0.14506(5) 0.29380(4) 0.91845(4) 0.05489(19) 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
C1 C2 1.413(9) . ?
C1 C6 1.418(8) . ?
C1 Ni1 1.888(6) . ?
C2 C3 1.400(9) . ?
C2 C7 1.477(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(9) . ?
C6 C8 1.466(9) . ?
C7 N1 1.318(8) . ?
C7 S1 1.717(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.499(11) . ?
C9 N1 1.481(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.535(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N1 1.476(8) . ?
C8 N2 1.327(8) . ?
C8 S2 1.723(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.520(11) . ?
C14 N2 1.474(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.492(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.525(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.506(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 N2 1.474(8) . ?
S1 Ni1 2.1638(18) . ?
S2 Ni1 2.1788(17) . ?
Ni1 I1 2.5733(9) . ?

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
C2 C1 C6 117.8(6) . . ?
C2 C1 Ni1 121.3(5) . . ?
C6 C1 Ni1 120.0(5) . . ?
C1 C2 C7 114.2(6) . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 C7 124.5(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(6) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(6) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(6) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C8 114.4(6) . . ?
C5 C6 C1 119.5(6) . . ?
C5 C6 C8 125.6(6) . . ?
C2 C7 S1 114.3(4) . . ?
N1 C7 C2 123.1(6) . . ?
N1 C7 S1 122.6(5) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
N1 C9 H9A 109.8 . . ?
N1 C9 H9B 109.8 . . ?
N1 C9 C10 109.2(6) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.0(6) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 C10 108.5(6) . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 C11 110.2(6) . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N1 C13 C12 112.1(6) . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C6 C8 S2 115.0(5) . . ?
N2 C8 C6 123.1(6) . . ?
N2 C8 S2 121.8(5) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
N2 C14 H14A 109.8 . . ?
N2 C14 H14B 109.8 . . ?
N2 C14 C15 109.5(6) . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.0(7) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 C17 110.6(7) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 110.9(7) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N2 C18 C17 110.7(6) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
C7 N1 C9 125.1(5) . . ?
C7 N1 C13 122.0(5) . . ?
C13 N1 C9 112.5(5) . . ?
C8 N2 C14 124.7(6) . . ?
C8 N2 C18 122.5(5) . . ?
C14 N2 C18 112.3(5) . . ?
C7 S1 Ni1 102.0(2) . . ?
C8 S2 Ni1 100.0(2) . . ?
C1 Ni1 S1 86.9(2) . . ?
C1 Ni1 S2 87.9(2) . . ?
C1 Ni1 I1 177.2(2) . . ?
S1 Ni1 S2 174.65(7) . . ?
S1 Ni1 I1 92.32(5) . . ?
S2 Ni1 I1 92.76(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 6.8(10) . . . . ?
C1 C2 C7 N1 -166.1(6) . . . . ?
C1 C2 C7 S1 12.7(8) . . . . ?
C1 C6 C8 N2 161.0(7) . . . . ?
C1 C6 C8 S2 -18.8(8) . . . . ?
C2 C1 C6 C5 10.7(10) . . . . ?
C2 C1 C6 C8 -177.4(6) . . . . ?
C2 C1 Ni1 S1 6.6(6) . . . . ?
C2 C1 Ni1 S2 -171.9(6) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
C2 C7 N1 C9 23.5(11) . . . . ?
C2 C7 N1 C13 -163.3(6) . . . . ?
C2 C7 S1 Ni1 -7.3(5) . . . . ?
C3 C2 C7 N1 25.4(11) . . . . ?
C3 C2 C7 S1 -155.8(6) . . . . ?
C3 C4 C5 C6 -2.8(11) . . . . ?
C4 C5 C6 C1 -3.2(11) . . . . ?
C4 C5 C6 C8 -174.1(7) . . . . ?
C5 C6 C8 N2 -27.7(11) . . . . ?
C5 C6 C8 S2 152.5(6) . . . . ?
C6 C1 C2 C3 -12.6(10) . . . . ?
C6 C1 C2 C7 178.4(6) . . . . ?
C6 C1 Ni1 S1 175.0(6) . . . . ?
C6 C1 Ni1 S2 -3.5(6) . . . . ?
C6 C8 N2 C14 -21.9(11) . . . . ?
C6 C8 N2 C18 167.3(7) . . . . ?
C6 C8 S2 Ni1 14.5(5) . . . . ?
C7 C2 C3 C4 174.7(6) . . . . ?
C9 C10 C11 C12 -58.1(8) . . . . ?
C10 C9 N1 C7 117.5(7) . . . . ?
C10 C9 N1 C13 -56.2(8) . . . . ?
C10 C11 C12 C13 55.7(8) . . . . ?
C11 C12 C13 N1 -56.1(8) . . . . ?
C12 C13 N1 C7 -117.4(7) . . . . ?
C12 C13 N1 C9 56.5(8) . . . . ?
C14 C15 C16 C17 54.3(10) . . . . ?
C15 C14 N2 C8 -113.6(8) . . . . ?
C15 C14 N2 C18 58.0(8) . . . . ?
C15 C16 C17 C18 -53.7(10) . . . . ?
C16 C17 C18 N2 55.5(9) . . . . ?
C17 C18 N2 C8 113.1(8) . . . . ?
C17 C18 N2 C14 -58.7(8) . . . . ?
N1 C7 S1 Ni1 171.5(5) . . . . ?
N1 C9 C10 C11 57.6(8) . . . . ?
N2 C8 S2 Ni1 -165.4(5) . . . . ?
N2 C14 C15 C16 -56.0(8) . . . . ?
S1 C7 N1 C9 -155.2(6) . . . . ?
S1 C7 N1 C13 17.9(10) . . . . ?
S2 C8 N2 C14 157.9(6) . . . . ?
S2 C8 N2 C18 -12.9(10) . . . . ?
Ni1 C1 C2 C3 156.1(5) . . . . ?
Ni1 C1 C2 C7 -12.9(9) . . . . ?
Ni1 C1 C6 C5 -158.1(5) . . . . ?
Ni1 C1 C6 C8 13.8(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
