# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2210261'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.927 F0.073 N'
_chemical_formula_sum            'C20 H11 Cl0.93 F0.07 N5 Ni S4'
_chemical_formula_weight         542.54
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.108(2)
_cell_length_b                   26.230(5)
_cell_length_c                   7.3716(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.496(5)
_cell_angle_gamma                90
_cell_volume                     2285.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.085
_cell_measurement_theta_min      2.320
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    1.341
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.8031.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1098
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            38631
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3134
_reflns_number_total             4241
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.031
_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)+(0.0261P)²+0.4686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.26859(3) 0.27524(2) 0.53811(4) 0.04801(12) Uani 1 1 d . . . . .
S1 S 0.13091(6) 0.22471(3) 0.43015(10) 0.05477(19) Uani 1 1 d . . . . .
S2 S 0.38248(6) 0.21303(3) 0.62336(10) 0.05567(19) Uani 1 1 d . . . . .
S3 S 0.16010(6) 0.33915(3) 0.44195(10) 0.05467(19) Uani 1 1 d . . . . .
S4 S 0.40996(6) 0.32365(3) 0.64567(10) 0.05648(19) Uani 1 1 d . . . . .
F1 F 0.73988(10) 0.33217(4) 0.99892(12) 0.0963(5) Uani 0.073(7) 1 d . . P . .
Cl1 Cl 0.73988(10) 0.33217(4) 0.99892(12) 0.0963(5) Uani 0.927(7) 1 d . . P . .
N1 N 0.0613(2) 0.08830(11) 0.3611(4) 0.0873(9) Uani 1 1 d . . . . .
N2 N 0.4030(2) 0.07382(11) 0.6111(4) 0.0843(8) Uani 1 1 d . . . . .
N3 N 0.1684(3) 0.47870(11) 0.3839(4) 0.0874(9) Uani 1 1 d . . . . .
N4 N 0.5102(3) 0.45405(11) 0.6614(4) 0.0940(9) Uani 1 1 d . . . . .
N5 N 0.77880(19) 0.07771(8) 0.8808(3) 0.0535(6) Uani 1 1 d . . . . .
C1 C 0.1201(2) 0.12214(12) 0.4093(4) 0.0588(7) Uani 1 1 d . . . . .
C2 C 0.1901(2) 0.16541(10) 0.4683(3) 0.0494(6) Uani 1 1 d . . . . .
C3 C 0.3018(2) 0.16025(10) 0.5524(3) 0.0477(6) Uani 1 1 d . . . . .
C4 C 0.3566(2) 0.11176(12) 0.5845(4) 0.0586(7) Uani 1 1 d . . . . .
C5 C 0.2056(3) 0.43998(13) 0.4347(4) 0.0623(8) Uani 1 1 d . . . . .
C6 C 0.2500(2) 0.39060(11) 0.4938(3) 0.0518(7) Uani 1 1 d . . . . .
C7 C 0.3598(2) 0.38369(10) 0.5832(3) 0.0509(6) Uani 1 1 d . . . . .
C8 C 0.4412(3) 0.42394(12) 0.6253(4) 0.0635(8) Uani 1 1 d . . . . .
C9 C 0.8762(3) 0.07123(13) 0.8273(5) 0.0775(9) Uani 1 1 d . . . . .
H9 H 0.9431 0.0833 0.9016 0.093 Uiso 1 1 calc R U . . .
C10 C 0.8784(4) 0.04717(14) 0.6654(6) 0.0943(12) Uani 1 1 d . . . . .
H10 H 0.9463 0.0431 0.6277 0.113 Uiso 1 1 calc R U . . .
C11 C 0.7793(4) 0.02876(13) 0.5572(5) 0.0873(11) Uani 1 1 d . . . . .
H11 H 0.7795 0.0118 0.4465 0.105 Uiso 1 1 calc R U . . .
C12 C 0.6814(3) 0.03582(13) 0.6151(5) 0.0824(10) Uani 1 1 d . . . . .
H12 H 0.6133 0.0241 0.5431 0.099 Uiso 1 1 calc R U . . .
C13 C 0.6832(3) 0.05991(11) 0.7775(4) 0.0657(8) Uani 1 1 d . . . . .
H13 H 0.6160 0.0641 0.8178 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7781(3) 0.10508(12) 1.0570(4) 0.0671(8) Uani 1 1 d . . . . .
H14A H 0.8467 0.0968 1.1473 0.081 Uiso 1 1 calc R U . . .
H14B H 0.7143 0.0933 1.1058 0.081 Uiso 1 1 calc R U . . .
C15 C 0.7703(2) 0.16219(11) 1.0326(3) 0.0519(7) Uani 1 1 d . . . . .
C16 C 0.6671(2) 0.18514(13) 0.9666(4) 0.0656(8) Uani 1 1 d . . . . .
H16 H 0.6028 0.1651 0.9298 0.079 Uiso 1 1 calc R U . . .
C17 C 0.6582(3) 0.23740(13) 0.9545(4) 0.0709(9) Uani 1 1 d . . . . .
H17 H 0.5882 0.2527 0.9104 0.085 Uiso 1 1 calc R U . . .
C18 C 0.7529(3) 0.26655(12) 1.0079(4) 0.0590(8) Uani 1 1 d . . . . .
C19 C 0.8566(3) 0.24503(14) 1.0711(4) 0.0721(9) Uani 1 1 d . . . . .
H19 H 0.9207 0.2653 1.1057 0.086 Uiso 1 1 calc R U . . .
C20 C 0.8644(2) 0.19249(13) 1.0829(4) 0.0681(8) Uani 1 1 d . . . . .
H20 H 0.9347 0.1774 1.1256 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1436(8) . ?
Ni1 S2 2.1409(8) . ?
Ni1 S3 2.1531(8) . ?
Ni1 S4 2.1409(8) . ?
S1 C2 1.710(3) . ?
S2 C3 1.710(3) . ?
S3 C6 1.724(3) . ?
S4 C7 1.715(3) . ?
F1 C18 1.729(3) . ?
N1 C1 1.146(4) . ?
N2 C4 1.139(4) . ?
N3 C5 1.141(4) . ?
N4 C8 1.139(4) . ?
N5 C9 1.332(4) . ?
N5 C13 1.325(3) . ?
N5 C14 1.486(3) . ?
C1 C2 1.427(4) . ?
C2 C3 1.367(4) . ?
C3 C4 1.430(4) . ?
C5 C6 1.433(4) . ?
C6 C7 1.362(4) . ?
C7 C8 1.432(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.356(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.357(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.350(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.509(4) . ?
C15 C16 1.377(4) . ?
C15 C20 1.373(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(4) . ?
C18 C19 1.363(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9300 . ?

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 S3 89.38(3) . . ?
S2 Ni1 S1 92.15(3) . . ?
S2 Ni1 S3 176.75(3) . . ?
S4 Ni1 S1 178.09(3) . . ?
S4 Ni1 S2 86.04(3) . . ?
S4 Ni1 S3 92.41(3) . . ?
C2 S1 Ni1 103.69(10) . . ?
C3 S2 Ni1 103.79(10) . . ?
C6 S3 Ni1 103.03(10) . . ?
C7 S4 Ni1 103.70(10) . . ?
C9 N5 C14 119.6(3) . . ?
C13 N5 C9 120.3(3) . . ?
C13 N5 C14 120.2(3) . . ?
N1 C1 C2 178.0(3) . . ?
C1 C2 S1 118.2(2) . . ?
C3 C2 S1 120.2(2) . . ?
C3 C2 C1 121.6(3) . . ?
C2 C3 S2 120.1(2) . . ?
C2 C3 C4 122.7(2) . . ?
C4 C3 S2 117.1(2) . . ?
N2 C4 C3 178.1(3) . . ?
N3 C5 C6 178.2(4) . . ?
C5 C6 S3 117.5(2) . . ?
C7 C6 S3 120.4(2) . . ?
C7 C6 C5 122.0(3) . . ?
C6 C7 S4 120.3(2) . . ?
C6 C7 C8 124.1(3) . . ?
C8 C7 S4 115.6(2) . . ?
N4 C8 C7 176.4(4) . . ?
N5 C9 H9 119.8 . . ?
N5 C9 C10 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.5(4) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
N5 C13 C12 121.3(3) . . ?
N5 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
N5 C14 H14A 109.0 . . ?
N5 C14 H14B 109.0 . . ?
N5 C14 C15 112.8(2) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C16 C15 C14 120.3(3) . . ?
C20 C15 C14 121.0(3) . . ?
C20 C15 C16 118.6(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 F1 118.9(3) . . ?
C19 C18 F1 119.7(3) . . ?
C19 C18 C17 121.4(3) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(3) . . ?
C20 C19 H19 120.7 . . ?
C15 C20 C19 121.2(3) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?

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 S1 C2 C1 -179.23(18) . . . . ?
Ni1 S1 C2 C3 0.4(2) . . . . ?
Ni1 S2 C3 C2 -1.9(2) . . . . ?
Ni1 S2 C3 C4 177.78(18) . . . . ?
Ni1 S3 C6 C5 175.63(19) . . . . ?
Ni1 S3 C6 C7 -2.6(2) . . . . ?
Ni1 S4 C7 C6 2.8(2) . . . . ?
Ni1 S4 C7 C8 -175.05(18) . . . . ?
S1 C2 C3 S2 1.0(3) . . . . ?
S1 C2 C3 C4 -178.63(19) . . . . ?
S3 C6 C7 S4 -0.1(3) . . . . ?
S3 C6 C7 C8 177.5(2) . . . . ?
F1 C18 C19 C20 177.9(2) . . . . ?
N5 C9 C10 C11 -0.9(6) . . . . ?
N5 C14 C15 C16 81.6(3) . . . . ?
N5 C14 C15 C20 -101.3(3) . . . . ?
C1 C2 C3 S2 -179.32(19) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C5 C6 C7 S4 -178.3(2) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C9 N5 C13 C12 -1.3(5) . . . . ?
C9 N5 C14 C15 85.5(3) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C11 C12 C13 N5 1.2(5) . . . . ?
C13 N5 C9 C10 1.1(5) . . . . ?
C13 N5 C14 C15 -94.5(3) . . . . ?
C14 N5 C9 C10 -178.8(3) . . . . ?
C14 N5 C13 C12 178.6(3) . . . . ?
C14 C15 C16 C17 176.0(3) . . . . ?
C14 C15 C20 C19 -176.1(3) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C15 C20 C19 1.1(4) . . . . ?
C16 C17 C18 F1 -178.0(2) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C20 C15 C16 C17 -1.2(4) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2210276'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.615 F0.385 N'
_chemical_formula_sum            'C20 H11 Cl0.61 F0.39 N5 Ni S4'
_chemical_formula_weight         537.40
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.1691(17)
_cell_length_b                   26.251(4)
_cell_length_c                   7.3843(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.348(5)
_cell_angle_gamma                90
_cell_volume                     2304.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7118
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.587
_cell_measurement_theta_min      2.890
_shelx_estimated_absorpt_T_max   0.746
_shelx_estimated_absorpt_T_min   0.660
_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0701 after correction.
The Ratio of minimum to maximum transmission is 0.7936.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            36188
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.891
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3200
_reflns_number_total             4265
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.074
_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)+(0.0314P)²+2.4385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.26993(4) 0.27602(2) 0.53514(7) 0.04467(16) Uani 1 1 d . . . . .
S1 S 0.13190(8) 0.22548(4) 0.42854(15) 0.0528(3) Uani 1 1 d . . . . .
S2 S 0.38330(8) 0.21348(4) 0.61892(15) 0.0527(3) Uani 1 1 d . . . . .
S3 S 0.16128(8) 0.34018(4) 0.44120(15) 0.0517(3) Uani 1 1 d . . . . .
S4 S 0.41100(8) 0.32453(4) 0.64141(15) 0.0540(3) Uani 1 1 d . . . . .
F1 F 0.74284(19) 0.33167(7) 0.9976(2) 0.0992(10) Uani 0.385(11) 1 d . . P . .
Cl1 Cl 0.74284(19) 0.33167(7) 0.9976(2) 0.0992(10) Uani 0.615(11) 1 d . . P . .
N1 N 0.0610(4) 0.08899(16) 0.3613(7) 0.0870(13) Uani 1 1 d . . . . .
N2 N 0.4031(4) 0.07387(15) 0.6078(6) 0.0822(13) Uani 1 1 d . . . . .
N3 N 0.1693(4) 0.48010(16) 0.3860(7) 0.0876(14) Uani 1 1 d . . . . .
N4 N 0.5105(4) 0.45503(17) 0.6607(6) 0.0915(14) Uani 1 1 d . . . . .
N5 N 0.7786(3) 0.07971(12) 0.8786(5) 0.0534(8) Uani 1 1 d . . . . .
C1 C 0.1197(4) 0.12253(18) 0.4084(6) 0.0606(11) Uani 1 1 d . . . . .
C2 C 0.1907(3) 0.16569(15) 0.4680(5) 0.0469(9) Uani 1 1 d . . . . .
C3 C 0.3031(3) 0.16051(15) 0.5501(5) 0.0463(9) Uani 1 1 d . . . . .
C4 C 0.3561(3) 0.11235(17) 0.5815(6) 0.0570(11) Uani 1 1 d . . . . .
C5 C 0.2053(4) 0.44154(18) 0.4347(6) 0.0618(12) Uani 1 1 d . . . . .
C6 C 0.2509(3) 0.39190(15) 0.4934(5) 0.0504(10) Uani 1 1 d . . . . .
C7 C 0.3611(3) 0.38473(15) 0.5806(5) 0.0492(10) Uani 1 1 d . . . . .
C8 C 0.4406(4) 0.42543(18) 0.6244(6) 0.0620(12) Uani 1 1 d . . . . .
C9 C 0.8754(4) 0.07361(19) 0.8246(8) 0.0790(15) Uani 1 1 d . . . . .
H9 H 0.941531 0.086415 0.897542 0.095 Uiso 1 1 calc R U . . .
C10 C 0.8787(6) 0.0489(2) 0.6642(10) 0.101(2) Uani 1 1 d . . . . .
H10 H 0.946589 0.044410 0.627654 0.121 Uiso 1 1 calc R U . . .
C11 C 0.7798(6) 0.0305(2) 0.5564(8) 0.0942(19) Uani 1 1 d . . . . .
H11 H 0.780047 0.013844 0.445357 0.113 Uiso 1 1 calc R U . . .
C12 C 0.6819(5) 0.03715(19) 0.6144(8) 0.0822(16) Uani 1 1 d . . . . .
H12 H 0.614558 0.025037 0.543299 0.099 Uiso 1 1 calc R U . . .
C13 C 0.6834(4) 0.06156(17) 0.7769(7) 0.0661(12) Uani 1 1 d . . . . .
H13 H 0.616663 0.065629 0.817544 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7768(4) 0.10678(18) 1.0570(6) 0.0693(13) Uani 1 1 d . . . . .
H14A H 0.844316 0.098240 1.148145 0.083 Uiso 1 1 calc R U . . .
H14B H 0.712497 0.095254 1.103972 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7704(3) 0.16398(16) 1.0310(5) 0.0508(10) Uani 1 1 d . . . . .
C16 C 0.6687(3) 0.18779(19) 0.9619(7) 0.0690(13) Uani 1 1 d . . . . .
H16 H 0.604389 0.168173 0.922991 0.083 Uiso 1 1 calc R U . . .
C17 C 0.6612(4) 0.2398(2) 0.9498(7) 0.0755(14) Uani 1 1 d . . . . .
H17 H 0.592224 0.255296 0.903100 0.091 Uiso 1 1 calc R U . . .
C18 C 0.7558(4) 0.26911(18) 1.0069(5) 0.0617(12) Uani 1 1 d . . . . .
C19 C 0.8578(4) 0.2469(2) 1.0738(6) 0.0695(13) Uani 1 1 d . . . . .
H19 H 0.921991 0.266728 1.111180 0.083 Uiso 1 1 calc R U . . .
C20 C 0.8639(4) 0.19449(18) 1.0851(6) 0.0649(12) Uani 1 1 d . . . . .
H20 H 0.933259 0.179239 1.130526 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1530(11) . ?
Ni1 S2 2.1486(11) . ?
Ni1 S3 2.1618(11) . ?
Ni1 S4 2.1468(11) . ?
S1 C2 1.724(4) . ?
S2 C3 1.712(4) . ?
S3 C6 1.732(4) . ?
S4 C7 1.718(4) . ?
F1 C18 1.650(5) . ?
N1 C1 1.141(5) . ?
N2 C4 1.156(5) . ?
N3 C5 1.131(5) . ?
N4 C8 1.140(5) . ?
N5 C9 1.331(6) . ?
N5 C13 1.328(5) . ?
N5 C14 1.501(5) . ?
C1 C2 1.435(6) . ?
C2 C3 1.380(5) . ?
C3 C4 1.416(6) . ?
C5 C6 1.445(6) . ?
C6 C7 1.371(5) . ?
C7 C8 1.432(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.358(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.360(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.357(7) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.514(6) . ?
C15 C16 1.382(6) . ?
C15 C20 1.379(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(6) . ?
C18 C19 1.365(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(6) . ?
C20 H20 0.9300 . ?

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 S3 89.26(4) . . ?
S2 Ni1 S1 92.13(4) . . ?
S2 Ni1 S3 177.03(5) . . ?
S4 Ni1 S1 178.27(5) . . ?
S4 Ni1 S2 86.21(4) . . ?
S4 Ni1 S3 92.38(4) . . ?
C2 S1 Ni1 103.67(14) . . ?
C3 S2 Ni1 104.18(13) . . ?
C6 S3 Ni1 103.11(14) . . ?
C7 S4 Ni1 103.86(14) . . ?
C9 N5 C14 120.0(4) . . ?
C13 N5 C9 120.6(4) . . ?
C13 N5 C14 119.4(4) . . ?
N1 C1 C2 178.2(5) . . ?
C1 C2 S1 117.8(3) . . ?
C3 C2 S1 120.0(3) . . ?
C3 C2 C1 122.1(4) . . ?
C2 C3 S2 119.9(3) . . ?
C2 C3 C4 122.3(4) . . ?
C4 C3 S2 117.8(3) . . ?
N2 C4 C3 177.5(5) . . ?
N3 C5 C6 178.9(5) . . ?
C5 C6 S3 117.2(3) . . ?
C7 C6 S3 120.2(3) . . ?
C7 C6 C5 122.6(4) . . ?
C6 C7 S4 120.3(3) . . ?
C6 C7 C8 123.4(4) . . ?
C8 C7 S4 116.3(3) . . ?
N4 C8 C7 174.6(5) . . ?
N5 C9 H9 119.6 . . ?
N5 C9 C10 120.7(5) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(5) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.3 . . ?
N5 C13 C12 121.0(5) . . ?
N5 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N5 C14 H14A 109.3 . . ?
N5 C14 H14B 109.3 . . ?
N5 C14 C15 111.6(3) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C16 C15 C14 120.9(4) . . ?
C20 C15 C14 121.5(4) . . ?
C20 C15 C16 117.5(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(4) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 F1 118.6(4) . . ?
C19 C18 F1 120.8(4) . . ?
C19 C18 C17 120.7(5) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.7(4) . . ?
C20 C19 H19 120.6 . . ?
C15 C20 C19 122.1(4) . . ?
C15 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?

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 C2 C1 -178.8(3) . . . . ?
Ni1 S1 C2 C3 -0.5(3) . . . . ?
Ni1 S2 C3 C2 -2.3(3) . . . . ?
Ni1 S2 C3 C4 178.1(3) . . . . ?
Ni1 S3 C6 C5 175.6(3) . . . . ?
Ni1 S3 C6 C7 -2.1(4) . . . . ?
Ni1 S4 C7 C6 3.1(4) . . . . ?
Ni1 S4 C7 C8 -176.2(3) . . . . ?
S1 C2 C3 S2 1.9(5) . . . . ?
S1 C2 C3 C4 -178.4(3) . . . . ?
S3 C6 C7 S4 -0.7(5) . . . . ?
S3 C6 C7 C8 178.6(3) . . . . ?
F1 C18 C19 C20 177.7(4) . . . . ?
N5 C9 C10 C11 0.7(9) . . . . ?
N5 C14 C15 C16 81.4(5) . . . . ?
N5 C14 C15 C20 -102.4(5) . . . . ?
C1 C2 C3 S2 -179.8(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C5 C6 C7 S4 -178.3(3) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C9 N5 C13 C12 -1.1(7) . . . . ?
C9 N5 C14 C15 84.5(5) . . . . ?
C9 C10 C11 C12 -0.7(9) . . . . ?
C10 C11 C12 C13 -0.1(9) . . . . ?
C11 C12 C13 N5 1.0(8) . . . . ?
C13 N5 C9 C10 0.3(7) . . . . ?
C13 N5 C14 C15 -96.2(5) . . . . ?
C14 N5 C9 C10 179.5(5) . . . . ?
C14 N5 C13 C12 179.6(4) . . . . ?
C14 C15 C16 C17 175.6(4) . . . . ?
C14 C15 C20 C19 -175.5(4) . . . . ?
C15 C16 C17 C18 0.0(8) . . . . ?
C16 C15 C20 C19 0.8(7) . . . . ?
C16 C17 C18 F1 -177.8(4) . . . . ?
C16 C17 C18 C19 0.7(7) . . . . ?
C17 C18 C19 C20 -0.7(7) . . . . ?
C18 C19 C20 C15 0.0(7) . . . . ?
C20 C15 C16 C17 -0.8(7) . . . . ?

_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2210273'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.132 F0.868 N'
_chemical_formula_sum            'C20 H11 Cl0.13 F0.87 N5 Ni S4'
_chemical_formula_weight         529.47
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.1411(5)
_cell_length_b                   25.9867(11)
_cell_length_c                   7.3406(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.8663(14)
_cell_angle_gamma                90
_cell_volume                     2266.52(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.971
_cell_measurement_theta_min      2.836
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.659
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0811 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            40602
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3476
_reflns_number_total             4217
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.148
_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)+(0.0267P)²+2.1660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.27189(3) 0.27823(2) 0.52597(6) 0.04649(14) Uani 1 1 d . . . . .
S1 S 0.13359(7) 0.22771(4) 0.42258(13) 0.0548(2) Uani 1 1 d . . . . .
S2 S 0.38454(7) 0.21510(3) 0.60822(13) 0.0544(2) Uani 1 1 d . . . . .
S3 S 0.16311(7) 0.34281(4) 0.43591(13) 0.0546(2) Uani 1 1 d . . . . .
S4 S 0.41249(7) 0.32703(4) 0.63105(13) 0.0562(2) Uani 1 1 d . . . . .
F1 F 0.7541(2) 0.32896(9) 0.9935(3) 0.1057(15) Uani 0.868(11) 1 d . . P . .
Cl1 Cl 0.7541(2) 0.32896(9) 0.9935(3) 0.1057(15) Uani 0.132(11) 1 d . . P . .
N1 N 0.0613(3) 0.09033(14) 0.3584(6) 0.0895(12) Uani 1 1 d . . . . .
N2 N 0.4012(3) 0.07440(14) 0.6005(5) 0.0866(11) Uani 1 1 d . . . . .
N3 N 0.1695(3) 0.48408(14) 0.3900(6) 0.0917(12) Uani 1 1 d . . . . .
N4 N 0.5114(4) 0.45822(16) 0.6626(6) 0.1009(13) Uani 1 1 d . . . . .
N5 N 0.7764(2) 0.08425(11) 0.8733(4) 0.0571(7) Uani 1 1 d . . . . .
C1 C 0.1202(3) 0.12459(16) 0.4046(5) 0.0622(10) Uani 1 1 d . . . . .
C2 C 0.1920(3) 0.16754(14) 0.4620(5) 0.0533(9) Uani 1 1 d . . . . .
C3 C 0.3038(3) 0.16203(13) 0.5422(4) 0.0485(8) Uani 1 1 d . . . . .
C4 C 0.3559(3) 0.11295(15) 0.5734(5) 0.0590(9) Uani 1 1 d . . . . .
C5 C 0.2062(3) 0.44489(16) 0.4360(5) 0.0652(10) Uani 1 1 d . . . . .
C6 C 0.2515(3) 0.39473(13) 0.4898(5) 0.0520(8) Uani 1 1 d . . . . .
C7 C 0.3619(3) 0.38789(13) 0.5765(4) 0.0505(8) Uani 1 1 d . . . . .
C8 C 0.4412(4) 0.42852(16) 0.6229(5) 0.0667(10) Uani 1 1 d . . . . .
C9 C 0.8730(4) 0.07841(18) 0.8202(7) 0.0853(13) Uani 1 1 d . . . . .
H9 H 0.938636 0.091612 0.893203 0.102 Uiso 1 1 calc R U . . .
C10 C 0.8773(6) 0.0533(2) 0.6600(10) 0.1124(19) Uani 1 1 d . . . . .
H10 H 0.945660 0.048718 0.623694 0.135 Uiso 1 1 calc R U . . .
C11 C 0.7798(6) 0.03480(19) 0.5522(7) 0.1015(18) Uani 1 1 d . . . . .
H11 H 0.780707 0.018437 0.439845 0.122 Uiso 1 1 calc R U . . .
C12 C 0.6825(5) 0.04062(18) 0.6114(8) 0.0946(15) Uani 1 1 d . . . . .
H12 H 0.615819 0.027527 0.541159 0.114 Uiso 1 1 calc R U . . .
C13 C 0.6819(3) 0.06527(16) 0.7713(6) 0.0726(11) Uani 1 1 d . . . . .
H13 H 0.614607 0.069167 0.811573 0.087 Uiso 1 1 calc R U . . .
C14 C 0.7730(4) 0.11195(16) 1.0501(5) 0.0735(11) Uani 1 1 d . . . . .
H14A H 0.839121 0.102775 1.142953 0.088 Uiso 1 1 calc R U . . .
H14B H 0.707288 0.100756 1.095466 0.088 Uiso 1 1 calc R U . . .
C15 C 0.7689(3) 0.16944(14) 1.0274(5) 0.0545(9) Uani 1 1 d . . . . .
C16 C 0.6699(3) 0.19410(18) 0.9495(5) 0.0691(11) Uani 1 1 d . . . . .
H16 H 0.605451 0.174864 0.904550 0.083 Uiso 1 1 calc R U . . .
C17 C 0.6657(3) 0.24668(18) 0.9376(6) 0.0751(12) Uani 1 1 d . . . . .
H17 H 0.598704 0.263211 0.885249 0.090 Uiso 1 1 calc R U . . .
C18 C 0.7603(4) 0.27441(16) 1.0031(5) 0.0648(10) Uani 1 1 d . . . . .
C19 C 0.8598(3) 0.25182(16) 1.0780(5) 0.0679(11) Uani 1 1 d . . . . .
H19 H 0.923892 0.271489 1.120757 0.081 Uiso 1 1 calc R U . . .
C20 C 0.8635(3) 0.19876(16) 1.0892(5) 0.0669(10) Uani 1 1 d . . . . .
H20 H 0.931262 0.182571 1.139501 0.080 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1435(10) . ?
Ni1 S2 2.1417(10) . ?
Ni1 S3 2.1537(10) . ?
Ni1 S4 2.1391(10) . ?
S1 C2 1.716(4) . ?
S2 C3 1.704(3) . ?
S3 C6 1.719(4) . ?
S4 C7 1.714(4) . ?
F1 C18 1.420(4) . ?
N1 C1 1.149(5) . ?
N2 C4 1.141(5) . ?
N3 C5 1.135(5) . ?
N4 C8 1.142(5) . ?
N5 C9 1.319(5) . ?
N5 C13 1.329(5) . ?
N5 C14 1.492(5) . ?
C1 C2 1.425(5) . ?
C2 C3 1.372(5) . ?
C3 C4 1.421(5) . ?
C5 C6 1.438(5) . ?
C6 C7 1.373(5) . ?
C7 C8 1.422(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.355(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.349(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.339(6) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.503(5) . ?
C15 C16 1.379(5) . ?
C15 C20 1.375(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.357(6) . ?
C18 C19 1.354(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(6) . ?
C20 H20 0.9300 . ?

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 S3 88.99(4) . . ?
S2 Ni1 S1 92.24(4) . . ?
S2 Ni1 S3 177.63(4) . . ?
S4 Ni1 S1 178.59(4) . . ?
S4 Ni1 S2 86.36(4) . . ?
S4 Ni1 S3 92.42(4) . . ?
C2 S1 Ni1 103.42(12) . . ?
C3 S2 Ni1 104.08(12) . . ?
C6 S3 Ni1 103.09(12) . . ?
C7 S4 Ni1 104.01(12) . . ?
C9 N5 C13 120.5(4) . . ?
C9 N5 C14 119.9(4) . . ?
C13 N5 C14 119.6(3) . . ?
N1 C1 C2 179.2(4) . . ?
C1 C2 S1 117.2(3) . . ?
C3 C2 S1 120.3(3) . . ?
C3 C2 C1 122.4(3) . . ?
C2 C3 S2 119.9(3) . . ?
C2 C3 C4 122.1(3) . . ?
C4 C3 S2 118.0(3) . . ?
N2 C4 C3 177.6(4) . . ?
N3 C5 C6 178.5(5) . . ?
C5 C6 S3 117.6(3) . . ?
C7 C6 S3 120.6(3) . . ?
C7 C6 C5 121.8(3) . . ?
C6 C7 S4 119.8(3) . . ?
C6 C7 C8 124.3(3) . . ?
C8 C7 S4 115.9(3) . . ?
N4 C8 C7 174.5(5) . . ?
N5 C9 H9 119.7 . . ?
N5 C9 C10 120.5(5) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(5) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(5) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
N5 C13 C12 120.8(4) . . ?
N5 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N5 C14 H14A 109.0 . . ?
N5 C14 H14B 109.0 . . ?
N5 C14 C15 112.9(3) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C16 C15 C14 120.9(4) . . ?
C20 C15 C14 120.5(4) . . ?
C20 C15 C16 118.5(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 F1 118.7(4) . . ?
C19 C18 F1 119.1(4) . . ?
C19 C18 C17 122.2(4) . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.2(4) . . ?
C20 C19 H19 120.9 . . ?
C15 C20 C19 121.2(4) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?

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 S1 C2 C1 -179.1(3) . . . . ?
Ni1 S1 C2 C3 -0.4(3) . . . . ?
Ni1 S2 C3 C2 -1.9(3) . . . . ?
Ni1 S2 C3 C4 178.3(2) . . . . ?
Ni1 S3 C6 C5 176.2(3) . . . . ?
Ni1 S3 C6 C7 -2.1(3) . . . . ?
Ni1 S4 C7 C6 1.8(3) . . . . ?
Ni1 S4 C7 C8 -176.8(2) . . . . ?
S1 C2 C3 S2 1.6(4) . . . . ?
S1 C2 C3 C4 -178.6(3) . . . . ?
S3 C6 C7 S4 0.2(4) . . . . ?
S3 C6 C7 C8 178.8(3) . . . . ?
F1 C18 C19 C20 178.8(3) . . . . ?
N5 C9 C10 C11 1.1(8) . . . . ?
N5 C14 C15 C16 78.4(5) . . . . ?
N5 C14 C15 C20 -103.6(4) . . . . ?
C1 C2 C3 S2 -179.7(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C5 C6 C7 S4 -178.0(3) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C9 N5 C13 C12 -1.1(6) . . . . ?
C9 N5 C14 C15 82.7(5) . . . . ?
C9 C10 C11 C12 -2.1(9) . . . . ?
C10 C11 C12 C13 1.5(8) . . . . ?
C11 C12 C13 N5 0.1(7) . . . . ?
C13 N5 C9 C10 0.5(7) . . . . ?
C13 N5 C14 C15 -97.9(4) . . . . ?
C14 N5 C9 C10 180.0(4) . . . . ?
C14 N5 C13 C12 179.5(4) . . . . ?
C14 C15 C16 C17 176.8(4) . . . . ?
C14 C15 C20 C19 -176.6(4) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C15 C20 C19 1.4(6) . . . . ?
C16 C17 C18 F1 -178.7(3) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C18 C19 C20 C15 -0.4(6) . . . . ?
C20 C15 C16 C17 -1.3(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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2210275'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.754 F0.246 N'
_chemical_formula_sum            'C20 H11 Cl0.75 F0.25 N5 Ni S4'
_chemical_formula_weight         539.69
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.1300(4)
_cell_length_b                   26.1989(9)
_cell_length_c                   7.3663(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.4024(11)
_cell_angle_gamma                90
_cell_volume                     2286.33(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.812
_cell_measurement_theta_min      2.898
_shelx_estimated_absorpt_T_max   0.742
_shelx_estimated_absorpt_T_min   0.655
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0725 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.8370.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            41808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.898
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3489
_reflns_number_total             4248
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.107
_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)+(0.0286P)²+1.3834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.26936(3) 0.27564(2) 0.53685(5) 0.04418(11) Uani 1 1 d . . . . .
S1 S 0.13153(6) 0.22510(3) 0.42973(11) 0.05166(19) Uani 1 1 d . . . . .
S2 S 0.38297(6) 0.21326(3) 0.62143(11) 0.05176(19) Uani 1 1 d . . . . .
S3 S 0.16073(6) 0.33967(3) 0.44172(10) 0.05108(19) Uani 1 1 d . . . . .
S4 S 0.41047(6) 0.32411(3) 0.64352(11) 0.05322(19) Uani 1 1 d . . . . .
F1 F 0.74113(13) 0.33201(4) 0.99869(16) 0.0957(7) Uani 0.246(9) 1 d . . P . .
Cl1 Cl 0.74113(13) 0.33201(4) 0.99869(16) 0.0957(7) Uani 0.754(9) 1 d . . P . .
N1 N 0.0614(3) 0.08854(12) 0.3608(5) 0.0847(9) Uani 1 1 d . . . . .
N2 N 0.4033(3) 0.07379(11) 0.6096(5) 0.0811(9) Uani 1 1 d . . . . .
N3 N 0.1686(3) 0.47943(11) 0.3853(5) 0.0847(9) Uani 1 1 d . . . . .
N4 N 0.5107(3) 0.45448(12) 0.6609(5) 0.0900(10) Uani 1 1 d . . . . .
N5 N 0.7786(2) 0.07873(9) 0.8798(3) 0.0520(6) Uani 1 1 d . . . . .
C1 C 0.1198(3) 0.12240(12) 0.4096(4) 0.0586(8) Uani 1 1 d . . . . .
C2 C 0.1907(2) 0.16551(11) 0.4680(4) 0.0464(6) Uani 1 1 d . . . . .
C3 C 0.3024(2) 0.16039(10) 0.5517(4) 0.0447(6) Uani 1 1 d . . . . .
C4 C 0.3565(3) 0.11196(12) 0.5827(4) 0.0560(7) Uani 1 1 d . . . . .
C5 C 0.2056(3) 0.44077(12) 0.4350(4) 0.0591(8) Uani 1 1 d . . . . .
C6 C 0.2508(2) 0.39112(11) 0.4938(4) 0.0494(7) Uani 1 1 d . . . . .
C7 C 0.3603(2) 0.38433(11) 0.5822(4) 0.0493(7) Uani 1 1 d . . . . .
C8 C 0.4410(3) 0.42484(13) 0.6246(5) 0.0619(8) Uani 1 1 d . . . . .
C9 C 0.8759(3) 0.07249(14) 0.8272(6) 0.0755(10) Uani 1 1 d . . . . .
H9 H 0.9424 0.0849 0.9013 0.091 Uiso 1 1 calc R U . . .
C10 C 0.8784(4) 0.04801(16) 0.6650(7) 0.0952(13) Uani 1 1 d . . . . .
H10 H 0.9464 0.0437 0.6278 0.114 Uiso 1 1 calc R U . . .
C11 C 0.7797(4) 0.02983(14) 0.5569(6) 0.0887(12) Uani 1 1 d . . . . .
H11 H 0.7800 0.0132 0.4455 0.106 Uiso 1 1 calc R U . . .
C12 C 0.6813(3) 0.03655(13) 0.6151(5) 0.0791(11) Uani 1 1 d . . . . .
H12 H 0.6136 0.0245 0.5436 0.095 Uiso 1 1 calc R U . . .
C13 C 0.6829(3) 0.06081(12) 0.7774(5) 0.0644(8) Uani 1 1 d . . . . .
H13 H 0.6160 0.0650 0.8180 0.077 Uiso 1 1 calc R U . . .
C14 C 0.7779(3) 0.10602(13) 1.0574(4) 0.0656(8) Uani 1 1 d . . . . .
H14A H 0.8462 0.0977 1.1477 0.079 Uiso 1 1 calc R U . . .
H14B H 0.7141 0.0943 1.1061 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7704(2) 0.16318(12) 1.0318(4) 0.0505(7) Uani 1 1 d . . . . .
C16 C 0.6682(3) 0.18650(13) 0.9642(5) 0.0650(9) Uani 1 1 d . . . . .
H16 H 0.6039 0.1666 0.9258 0.078 Uiso 1 1 calc R U . . .
C17 C 0.6596(3) 0.23865(14) 0.9525(5) 0.0710(9) Uani 1 1 d . . . . .
H17 H 0.5900 0.2540 0.9076 0.085 Uiso 1 1 calc R U . . .
C18 C 0.7541(3) 0.26790(12) 1.0074(4) 0.0585(8) Uani 1 1 d . . . . .
C19 C 0.8574(3) 0.24621(14) 1.0731(5) 0.0687(9) Uani 1 1 d . . . . .
H19 H 0.9215 0.2664 1.1091 0.082 Uiso 1 1 calc R U . . .
C20 C 0.8644(3) 0.19360(13) 1.0851(5) 0.0646(8) Uani 1 1 d . . . . .
H20 H 0.9342 0.1784 1.1301 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1457(8) . ?
Ni1 S2 2.1424(8) . ?
Ni1 S3 2.1552(8) . ?
Ni1 S4 2.1406(8) . ?
S1 C2 1.716(3) . ?
S2 C3 1.709(3) . ?
S3 C6 1.725(3) . ?
S4 C7 1.716(3) . ?
F1 C18 1.687(3) . ?
N1 C1 1.144(4) . ?
N2 C4 1.146(4) . ?
N3 C5 1.136(4) . ?
N4 C8 1.137(4) . ?
N5 C9 1.329(4) . ?
N5 C13 1.327(4) . ?
N5 C14 1.492(4) . ?
C1 C2 1.429(4) . ?
C2 C3 1.370(4) . ?
C3 C4 1.424(4) . ?
C5 C6 1.441(4) . ?
C6 C7 1.360(4) . ?
C7 C8 1.432(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.351(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(4) . ?
C15 C16 1.376(4) . ?
C15 C20 1.377(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(5) . ?
C18 C19 1.366(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(5) . ?
C20 H20 0.9300 . ?

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 S3 89.26(3) . . ?
S2 Ni1 S1 92.17(3) . . ?
S2 Ni1 S3 176.91(4) . . ?
S4 Ni1 S1 178.19(3) . . ?
S4 Ni1 S2 86.10(3) . . ?
S4 Ni1 S3 92.44(3) . . ?
C2 S1 Ni1 103.64(10) . . ?
C3 S2 Ni1 103.90(9) . . ?
C6 S3 Ni1 102.84(10) . . ?
C7 S4 Ni1 103.80(10) . . ?
C9 N5 C14 119.2(3) . . ?
C13 N5 C9 120.9(3) . . ?
C13 N5 C14 119.9(3) . . ?
N1 C1 C2 178.6(4) . . ?
C1 C2 S1 117.8(2) . . ?
C3 C2 S1 120.1(2) . . ?
C3 C2 C1 122.1(3) . . ?
C2 C3 S2 120.2(2) . . ?
C2 C3 C4 122.5(3) . . ?
C4 C3 S2 117.4(2) . . ?
N2 C4 C3 177.8(3) . . ?
N3 C5 C6 178.5(4) . . ?
C5 C6 S3 117.2(2) . . ?
C7 C6 S3 120.7(2) . . ?
C7 C6 C5 122.1(3) . . ?
C6 C7 S4 120.1(2) . . ?
C6 C7 C8 124.0(3) . . ?
C8 C7 S4 115.9(2) . . ?
N4 C8 C7 175.2(4) . . ?
N5 C9 H9 119.9 . . ?
N5 C9 C10 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.3 . . ?
N5 C13 C12 120.9(3) . . ?
N5 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N5 C14 H14A 109.2 . . ?
N5 C14 H14B 109.2 . . ?
N5 C14 C15 112.2(2) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 C20 118.2(3) . . ?
C20 C15 C14 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 F1 118.8(3) . . ?
C17 C18 C19 121.2(3) . . ?
C19 C18 F1 119.9(3) . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C15 C20 C19 121.6(3) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?

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 C2 C1 -179.5(2) . . . . ?
Ni1 S1 C2 C3 0.4(2) . . . . ?
Ni1 S2 C3 C2 -1.7(2) . . . . ?
Ni1 S2 C3 C4 177.6(2) . . . . ?
Ni1 S3 C6 C5 175.8(2) . . . . ?
Ni1 S3 C6 C7 -2.6(3) . . . . ?
Ni1 S4 C7 C6 2.7(3) . . . . ?
Ni1 S4 C7 C8 -175.4(2) . . . . ?
S1 C2 C3 S2 0.9(3) . . . . ?
S1 C2 C3 C4 -178.4(2) . . . . ?
S3 C6 C7 S4 -0.1(3) . . . . ?
S3 C6 C7 C8 177.9(2) . . . . ?
F1 C18 C19 C20 177.6(2) . . . . ?
N5 C9 C10 C11 -0.1(6) . . . . ?
N5 C14 C15 C16 81.1(4) . . . . ?
N5 C14 C15 C20 -102.6(3) . . . . ?
C1 C2 C3 S2 -179.2(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C5 C6 C7 S4 -178.3(2) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C9 N5 C13 C12 -1.2(5) . . . . ?
C9 N5 C14 C15 85.4(4) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 N5 0.8(6) . . . . ?
C13 N5 C9 C10 0.9(5) . . . . ?
C13 N5 C14 C15 -95.0(3) . . . . ?
C14 N5 C9 C10 -179.5(3) . . . . ?
C14 N5 C13 C12 179.2(3) . . . . ?
C14 C15 C16 C17 175.5(3) . . . . ?
C14 C15 C20 C19 -175.9(3) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C15 C20 C19 0.5(5) . . . . ?
C16 C17 C18 F1 -178.0(3) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C15 0.3(5) . . . . ?
C20 C15 C16 C17 -0.9(5) . . . . ?

_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_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2210274'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.852 F0.148 N'
_chemical_formula_sum            'C20 H11 Cl0.85 F0.15 N5 Ni S4'
_chemical_formula_weight         541.30
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.201(10)
_cell_length_b                   26.520(19)
_cell_length_c                   7.410(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.32(3)
_cell_angle_gamma                90
_cell_volume                     2343(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6579
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.28
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.301
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0841 after correction.
The Ratio of minimum to maximum transmission is 0.7275.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1095
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            42996
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.210
_diffrn_reflns_theta_max         25.210
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3248
_reflns_number_total             4176
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.019
_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)+(0.0620P)²+0.1765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.26892(3) 0.27542(2) 0.53742(5) 0.04994(14) Uani 1 1 d . . . . .
S1 S 0.13118(6) 0.22483(3) 0.42981(11) 0.0570(2) Uani 1 1 d . . . . .
S2 S 0.38274(6) 0.21319(3) 0.62266(11) 0.0575(2) Uani 1 1 d . . . . .
S3 S 0.16040(6) 0.33934(3) 0.44174(11) 0.0570(2) Uani 1 1 d . . . . .
S4 S 0.41017(6) 0.32385(3) 0.64480(11) 0.0591(2) Uani 1 1 d . . . . .
F1 F 0.74028(12) 0.33207(4) 0.99865(14) 0.1007(6) Uani 0.148(8) 1 d . . P . .
Cl1 Cl 0.74028(12) 0.33207(4) 0.99865(14) 0.1007(6) Uani 0.852(8) 1 d . . P . .
N1 N 0.0619(3) 0.08842(11) 0.3613(5) 0.0921(10) Uani 1 1 d . . . . .
N2 N 0.4034(3) 0.07378(11) 0.6102(5) 0.0880(9) Uani 1 1 d . . . . .
N3 N 0.1685(3) 0.47903(10) 0.3840(5) 0.0902(9) Uani 1 1 d . . . . .
N4 N 0.5105(3) 0.45409(11) 0.6619(5) 0.0980(10) Uani 1 1 d . . . . .
N5 N 0.77887(19) 0.07811(8) 0.8809(3) 0.0572(6) Uani 1 1 d . . . . .
C1 C 0.1197(3) 0.12232(11) 0.4088(4) 0.0617(8) Uani 1 1 d . . . . .
C2 C 0.1902(2) 0.16550(10) 0.4682(4) 0.0502(6) Uani 1 1 d . . . . .
C3 C 0.3019(2) 0.16033(10) 0.5512(4) 0.0496(6) Uani 1 1 d . . . . .
C4 C 0.3565(3) 0.11174(12) 0.5832(4) 0.0605(7) Uani 1 1 d . . . . .
C5 C 0.2052(3) 0.44019(12) 0.4346(5) 0.0672(8) Uani 1 1 d . . . . .
C6 C 0.2499(2) 0.39076(11) 0.4950(4) 0.0544(7) Uani 1 1 d . . . . .
C7 C 0.3600(2) 0.38387(10) 0.5818(4) 0.0545(7) Uani 1 1 d . . . . .
C8 C 0.4408(3) 0.42424(12) 0.6241(5) 0.0686(8) Uani 1 1 d . . . . .
C9 C 0.8766(3) 0.07178(13) 0.8279(6) 0.0819(10) Uani 1 1 d . . . . .
H9 H 0.9429 0.0839 0.9012 0.098 Uiso 1 1 calc R U . . .
C10 C 0.8784(4) 0.04738(14) 0.6655(7) 0.0999(13) Uani 1 1 d . . . . .
H10 H 0.9459 0.0429 0.6284 0.120 Uiso 1 1 calc R U . . .
C11 C 0.7793(4) 0.02947(13) 0.5569(5) 0.0928(13) Uani 1 1 d . . . . .
H11 H 0.7795 0.0132 0.4458 0.111 Uiso 1 1 calc R U . . .
C12 C 0.6813(4) 0.03601(13) 0.6152(5) 0.0857(11) Uani 1 1 d . . . . .
H12 H 0.6141 0.0240 0.5447 0.103 Uiso 1 1 calc R U . . .
C13 C 0.6832(3) 0.06028(11) 0.7768(5) 0.0688(8) Uani 1 1 d . . . . .
H13 H 0.6164 0.0647 0.8165 0.083 Uiso 1 1 calc R U . . .
C14 C 0.7778(3) 0.10543(12) 1.0564(4) 0.0707(9) Uani 1 1 d . . . . .
H14A H 0.8456 0.0973 1.1464 0.085 Uiso 1 1 calc R U . . .
H14B H 0.7144 0.0938 1.1049 0.085 Uiso 1 1 calc R U . . .
C15 C 0.7701(2) 0.16250(12) 1.0317(4) 0.0569(7) Uani 1 1 d . . . . .
C16 C 0.6680(2) 0.18592(13) 0.9656(5) 0.0689(9) Uani 1 1 d . . . . .
H16 H 0.6042 0.1662 0.9281 0.083 Uiso 1 1 calc R U . . .
C17 C 0.6584(3) 0.23766(14) 0.9539(5) 0.0768(10) Uani 1 1 d . . . . .
H17 H 0.5889 0.2526 0.9104 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7535(3) 0.26713(13) 1.0075(4) 0.0640(8) Uani 1 1 d . . . . .
C19 C 0.8567(3) 0.24539(13) 1.0715(5) 0.0761(9) Uani 1 1 d . . . . .
H19 H 0.9205 0.2653 1.1062 0.091 Uiso 1 1 calc R U . . .
C20 C 0.8642(3) 0.19273(13) 1.0834(5) 0.0701(9) Uani 1 1 d . . . . .
H20 H 0.9337 0.1778 1.1269 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1651(14) . ?
Ni1 S2 2.1627(14) . ?
Ni1 S3 2.1745(14) . ?
Ni1 S4 2.1605(14) . ?
S1 C2 1.729(3) . ?
S2 C3 1.731(3) . ?
S3 C6 1.739(3) . ?
S4 C7 1.733(3) . ?
F1 C18 1.730(4) . ?
N1 C1 1.150(4) . ?
N2 C4 1.154(4) . ?
N3 C5 1.153(4) . ?
N4 C8 1.151(4) . ?
N5 C9 1.344(4) . ?
N5 C13 1.341(4) . ?
N5 C14 1.491(4) . ?
C1 C2 1.443(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.447(4) . ?
C5 C6 1.453(4) . ?
C6 C7 1.372(4) . ?
C7 C8 1.444(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.525(4) . ?
C15 C16 1.384(4) . ?
C15 C20 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 C19 1.374(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.401(5) . ?
C20 H20 0.9300 . ?

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 S3 89.55(6) . . ?
S2 Ni1 S1 91.96(7) . . ?
S2 Ni1 S3 176.86(3) . . ?
S4 Ni1 S1 178.10(3) . . ?
S4 Ni1 S2 86.22(7) . . ?
S4 Ni1 S3 92.24(6) . . ?
C2 S1 Ni1 103.89(11) . . ?
C3 S2 Ni1 103.88(11) . . ?
C6 S3 Ni1 103.18(12) . . ?
C7 S4 Ni1 103.81(11) . . ?
C9 N5 C14 119.3(3) . . ?
C13 N5 C9 120.4(3) . . ?
C13 N5 C14 120.3(3) . . ?
N1 C1 C2 178.8(3) . . ?
C1 C2 S1 118.1(2) . . ?
C3 C2 S1 120.1(2) . . ?
C3 C2 C1 121.7(2) . . ?
C2 C3 S2 120.1(2) . . ?
C2 C3 C4 122.6(2) . . ?
C4 C3 S2 117.3(2) . . ?
N2 C4 C3 177.8(3) . . ?
N3 C5 C6 178.8(4) . . ?
C5 C6 S3 117.5(2) . . ?
C7 C6 S3 120.4(2) . . ?
C7 C6 C5 122.0(3) . . ?
C6 C7 S4 120.2(2) . . ?
C6 C7 C8 123.9(3) . . ?
C8 C7 S4 115.9(2) . . ?
N4 C8 C7 175.6(4) . . ?
N5 C9 H9 120.1 . . ?
N5 C9 C10 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
N5 C13 C12 121.6(3) . . ?
N5 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
N5 C14 H14A 109.0 . . ?
N5 C14 H14B 109.0 . . ?
N5 C14 C15 112.9(2) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 C20 117.9(3) . . ?
C20 C15 C14 121.0(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 F1 119.1(3) . . ?
C19 C18 F1 120.1(3) . . ?
C19 C18 C17 120.8(4) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.8(3) . . ?
C20 C19 H19 120.6 . . ?
C15 C20 C19 121.4(3) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?

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 C2 C1 -179.2(2) . . . . ?
Ni1 S1 C2 C3 0.1(3) . . . . ?
Ni1 S2 C3 C2 -2.3(3) . . . . ?
Ni1 S2 C3 C4 177.8(2) . . . . ?
Ni1 S3 C6 C5 175.1(2) . . . . ?
Ni1 S3 C6 C7 -1.4(3) . . . . ?
Ni1 S4 C7 C6 3.8(3) . . . . ?
Ni1 S4 C7 C8 -175.3(2) . . . . ?
S1 C2 C3 S2 1.6(3) . . . . ?
S1 C2 C3 C4 -178.6(2) . . . . ?
S3 C6 C7 S4 -1.7(4) . . . . ?
S3 C6 C7 C8 177.4(2) . . . . ?
F1 C18 C19 C20 177.7(2) . . . . ?
N5 C9 C10 C11 0.1(6) . . . . ?
N5 C14 C15 C16 81.5(4) . . . . ?
N5 C14 C15 C20 -101.7(3) . . . . ?
C1 C2 C3 S2 -179.2(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C5 C6 C7 S4 -178.0(2) . . . . ?
C5 C6 C7 C8 1.1(5) . . . . ?
C9 N5 C13 C12 -0.7(5) . . . . ?
C9 N5 C14 C15 85.3(3) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C11 C12 C13 N5 0.1(5) . . . . ?
C13 N5 C9 C10 0.6(5) . . . . ?
C13 N5 C14 C15 -94.4(3) . . . . ?
C14 N5 C9 C10 -179.0(3) . . . . ?
C14 N5 C13 C12 178.9(3) . . . . ?
C14 C15 C16 C17 175.7(3) . . . . ?
C14 C15 C20 C19 -176.1(3) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C15 C20 C19 0.7(5) . . . . ?
C16 C17 C18 F1 -178.2(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C15 0.2(5) . . . . ?
C20 C15 C16 C17 -1.2(5) . . . . ?

_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_1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2210282'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.261 F0.739 N'
_chemical_formula_sum            'C20 H11 Cl0.26 F0.74 N5 Ni S4'
_chemical_formula_weight         531.57
_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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 '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'

_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                   12.1396(12)
_cell_length_b                   26.017(3)
_cell_length_c                   7.3495(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.038(4)
_cell_angle_gamma                90
_cell_volume                     2270.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.165
_cell_measurement_theta_min      2.909
_shelx_estimated_absorpt_T_max   0.758
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1294 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.8404.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            50278
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3213
_reflns_number_total             4226
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.136
_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)+(0.0206P)²+3.0559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.27145(4) 0.27753(2) 0.52889(7) 0.04611(17) Uani 1 1 d . . . . .
S1 S 0.13311(9) 0.22699(4) 0.42467(15) 0.0544(3) Uani 1 1 d . . . . .
S2 S 0.38428(9) 0.21454(4) 0.61165(16) 0.0544(3) Uani 1 1 d . . . . .
S3 S 0.16267(9) 0.34196(4) 0.43768(15) 0.0537(3) Uani 1 1 d . . . . .
S4 S 0.41224(9) 0.32629(4) 0.63424(16) 0.0560(3) Uani 1 1 d . . . . .
F1 F 0.7502(3) 0.32982(10) 0.9952(3) 0.1080(16) Uani 0.739(12) 1 d . . P . .
Cl1 Cl 0.7502(3) 0.32982(10) 0.9952(3) 0.1080(16) Uani 0.261(12) 1 d . . P . .
N1 N 0.0612(4) 0.08990(17) 0.3600(7) 0.0876(14) Uani 1 1 d . . . . .
N2 N 0.4017(4) 0.07434(17) 0.6031(6) 0.0842(13) Uani 1 1 d . . . . .
N3 N 0.1697(4) 0.48288(17) 0.3893(7) 0.0919(15) Uani 1 1 d . . . . .
N4 N 0.5112(4) 0.45731(19) 0.6619(7) 0.0990(16) Uani 1 1 d . . . . .
N5 N 0.7774(3) 0.08287(13) 0.8752(5) 0.0566(9) Uani 1 1 d . . . . .
C1 C 0.1202(4) 0.1239(2) 0.4065(6) 0.0622(12) Uani 1 1 d . . . . .
C2 C 0.1914(4) 0.16704(17) 0.4647(5) 0.0524(11) Uani 1 1 d . . . . .
C3 C 0.3040(3) 0.16147(16) 0.5462(5) 0.0482(10) Uani 1 1 d . . . . .
C4 C 0.3560(4) 0.11261(19) 0.5761(6) 0.0579(11) Uani 1 1 d . . . . .
C5 C 0.2056(4) 0.44396(19) 0.4360(7) 0.0643(13) Uani 1 1 d . . . . .
C6 C 0.2510(3) 0.39365(16) 0.4907(6) 0.0521(11) Uani 1 1 d . . . . .
C7 C 0.3616(3) 0.38707(16) 0.5788(5) 0.0503(10) Uani 1 1 d . . . . .
C8 C 0.4409(4) 0.42773(19) 0.6230(6) 0.0642(12) Uani 1 1 d . . . . .
C9 C 0.8733(4) 0.0771(2) 0.8207(9) 0.0835(16) Uani 1 1 d . . . . .
H9 H 0.938982 0.090675 0.893032 0.100 Uiso 1 1 calc R U . . .
C10 C 0.8782(6) 0.0522(2) 0.6629(11) 0.110(2) Uani 1 1 d . . . . .
H10 H 0.946929 0.047467 0.628141 0.131 Uiso 1 1 calc R U . . .
C11 C 0.7805(7) 0.0337(2) 0.5532(8) 0.100(2) Uani 1 1 d . . . . .
H11 H 0.781600 0.017691 0.440572 0.119 Uiso 1 1 calc R U . . .
C12 C 0.6827(6) 0.0393(2) 0.6118(9) 0.0906(18) Uani 1 1 d . . . . .
H12 H 0.616021 0.026131 0.541556 0.109 Uiso 1 1 calc R U . . .
C13 C 0.6828(4) 0.06409(18) 0.7728(7) 0.0713(14) Uani 1 1 d . . . . .
H13 H 0.615574 0.068101 0.812931 0.086 Uiso 1 1 calc R U . . .
C14 C 0.7749(4) 0.11042(19) 1.0538(6) 0.0724(14) Uani 1 1 d . . . . .
H14A H 0.841892 0.101602 1.145650 0.087 Uiso 1 1 calc R U . . .
H14B H 0.709900 0.099030 1.100421 0.087 Uiso 1 1 calc R U . . .
C15 C 0.7695(4) 0.16788(18) 1.0286(6) 0.0538(11) Uani 1 1 d . . . . .
C16 C 0.6696(4) 0.1920(2) 0.9534(7) 0.0703(14) Uani 1 1 d . . . . .
H16 H 0.605188 0.172567 0.910120 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6643(4) 0.2446(2) 0.9419(7) 0.0756(15) Uani 1 1 d . . . . .
H17 H 0.596440 0.260883 0.891973 0.091 Uiso 1 1 calc R U . . .
C18 C 0.7587(4) 0.2728(2) 1.0038(6) 0.0639(13) Uani 1 1 d . . . . .
C19 C 0.8592(4) 0.2504(2) 1.0771(7) 0.0699(14) Uani 1 1 d . . . . .
H19 H 0.923340 0.270150 1.118258 0.084 Uiso 1 1 calc R U . . .
C20 C 0.8635(4) 0.1976(2) 1.0890(6) 0.0662(13) Uani 1 1 d . . . . .
H20 H 0.931655 0.181674 1.139024 0.079 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1446(12) . ?
Ni1 S2 2.1410(12) . ?
Ni1 S3 2.1526(12) . ?
Ni1 S4 2.1396(12) . ?
S1 C2 1.713(4) . ?
S2 C3 1.701(4) . ?
S3 C6 1.714(4) . ?
S4 C7 1.715(4) . ?
F1 C18 1.488(5) . ?
N1 C1 1.146(6) . ?
N2 C4 1.137(5) . ?
N3 C5 1.127(6) . ?
N4 C8 1.140(6) . ?
N5 C9 1.317(6) . ?
N5 C13 1.327(5) . ?
N5 C14 1.501(5) . ?
C1 C2 1.425(6) . ?
C2 C3 1.381(5) . ?
C3 C4 1.416(6) . ?
C5 C6 1.444(6) . ?
C6 C7 1.374(5) . ?
C7 C8 1.421(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.341(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.352(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.348(7) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.506(6) . ?
C15 C16 1.376(6) . ?
C15 C20 1.373(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.356(7) . ?
C18 C19 1.358(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(6) . ?
C20 H20 0.9300 . ?

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 S3 88.99(5) . . ?
S2 Ni1 S1 92.24(5) . . ?
S2 Ni1 S3 177.50(5) . . ?
S4 Ni1 S1 178.55(5) . . ?
S4 Ni1 S2 86.31(5) . . ?
S4 Ni1 S3 92.45(5) . . ?
C2 S1 Ni1 103.44(15) . . ?
C3 S2 Ni1 104.24(14) . . ?
C6 S3 Ni1 103.07(15) . . ?
C7 S4 Ni1 103.96(15) . . ?
C9 N5 C13 120.1(5) . . ?
C9 N5 C14 120.0(4) . . ?
C13 N5 C14 119.9(4) . . ?
N1 C1 C2 178.6(5) . . ?
C1 C2 S1 117.5(3) . . ?
C3 C2 S1 120.4(3) . . ?
C3 C2 C1 122.0(4) . . ?
C2 C3 S2 119.6(3) . . ?
C2 C3 C4 122.0(4) . . ?
C4 C3 S2 118.3(3) . . ?
N2 C4 C3 177.2(5) . . ?
N3 C5 C6 178.5(5) . . ?
C5 C6 S3 117.6(3) . . ?
C7 C6 S3 120.9(3) . . ?
C7 C6 C5 121.5(4) . . ?
C6 C7 S4 119.6(3) . . ?
C6 C7 C8 124.3(4) . . ?
C8 C7 S4 116.1(3) . . ?
N4 C8 C7 174.3(5) . . ?
N5 C9 H9 119.4 . . ?
N5 C9 C10 121.3(5) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(6) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
N5 C13 C12 121.1(5) . . ?
N5 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N5 C14 H14A 109.2 . . ?
N5 C14 H14B 109.2 . . ?
N5 C14 C15 112.0(4) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C16 C15 C14 121.0(4) . . ?
C20 C15 C14 120.5(4) . . ?
C20 C15 C16 118.4(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.5(5) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 F1 118.6(4) . . ?
C17 C18 C19 121.8(5) . . ?
C19 C18 F1 119.6(5) . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.2(5) . . ?
C20 C19 H19 120.9 . . ?
C15 C20 C19 121.6(4) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?

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 C2 C1 -178.8(3) . . . . ?
Ni1 S1 C2 C3 -0.3(4) . . . . ?
Ni1 S2 C3 C2 -1.6(4) . . . . ?
Ni1 S2 C3 C4 177.7(3) . . . . ?
Ni1 S3 C6 C5 176.2(3) . . . . ?
Ni1 S3 C6 C7 -2.5(4) . . . . ?
Ni1 S4 C7 C6 1.6(4) . . . . ?
Ni1 S4 C7 C8 -176.2(3) . . . . ?
S1 C2 C3 S2 1.4(5) . . . . ?
S1 C2 C3 C4 -177.9(3) . . . . ?
S3 C6 C7 S4 0.6(5) . . . . ?
S3 C6 C7 C8 178.2(3) . . . . ?
F1 C18 C19 C20 177.9(4) . . . . ?
N5 C9 C10 C11 2.1(10) . . . . ?
N5 C14 C15 C16 79.2(5) . . . . ?
N5 C14 C15 C20 -104.1(5) . . . . ?
C1 C2 C3 S2 179.8(3) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C5 C6 C7 S4 -178.0(3) . . . . ?
C5 C6 C7 C8 -0.4(7) . . . . ?
C9 N5 C13 C12 -0.5(7) . . . . ?
C9 N5 C14 C15 83.3(5) . . . . ?
C9 C10 C11 C12 -2.9(10) . . . . ?
C10 C11 C12 C13 2.0(10) . . . . ?
C11 C12 C13 N5 -0.4(9) . . . . ?
C13 N5 C9 C10 -0.4(8) . . . . ?
C13 N5 C14 C15 -97.0(5) . . . . ?
C14 N5 C9 C10 179.2(5) . . . . ?
C14 N5 C13 C12 179.9(5) . . . . ?
C14 C15 C16 C17 175.9(4) . . . . ?
C14 C15 C20 C19 -176.3(4) . . . . ?
C15 C16 C17 C18 0.6(8) . . . . ?
C16 C15 C20 C19 0.6(7) . . . . ?
C16 C17 C18 F1 -178.2(4) . . . . ?
C16 C17 C18 C19 0.1(8) . . . . ?
C17 C18 C19 C20 -0.5(7) . . . . ?
C18 C19 C20 C15 0.1(7) . . . . ?
C20 C15 C16 C17 -0.9(7) . . . . ?

_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_1_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2210278'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.297 F0.703 N'
_chemical_formula_sum            'C20 H11 Cl0.30 F0.70 N5 Ni S4'
_chemical_formula_weight         532.18
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.125(11)
_cell_length_b                   25.88(2)
_cell_length_c                   7.344(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.78(3)
_cell_angle_gamma                90
_cell_volume                     2256(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4267
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.918
_cell_measurement_theta_min      2.920
_shelx_estimated_absorpt_T_max   0.739
_shelx_estimated_absorpt_T_min   0.647
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0700 before and 0.0574 after correction.
The Ratio of minimum to maximum transmission is 0.7666.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1078
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20739
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.919
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3126
_reflns_number_total             4192
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.159
_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)+(0.0153P)²+4.7588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.27123(5) 0.27734(3) 0.52965(9) 0.0450(2) Uani 1 1 d . . . . .
S1 S 0.13292(10) 0.22684(6) 0.42511(19) 0.0532(4) Uani 1 1 d . . . . .
S2 S 0.38392(11) 0.21437(5) 0.6127(2) 0.0534(4) Uani 1 1 d . . . . .
S3 S 0.16244(11) 0.34172(5) 0.43798(19) 0.0524(4) Uani 1 1 d . . . . .
S4 S 0.41193(11) 0.32599(5) 0.6350(2) 0.0544(4) Uani 1 1 d . . . . .
F1 F 0.7492(3) 0.33015(11) 0.9960(4) 0.1055(18) Uani 0.703(15) 1 d . . P . .
Cl1 Cl 0.7492(3) 0.33015(11) 0.9960(4) 0.1055(18) Uani 0.297(15) 1 d . . P . .
N1 N 0.0616(5) 0.0899(2) 0.3600(8) 0.0850(17) Uani 1 1 d . . . . .
N2 N 0.4018(5) 0.0744(2) 0.6038(8) 0.0822(16) Uani 1 1 d . . . . .
N3 N 0.1696(5) 0.4825(2) 0.3890(8) 0.0910(18) Uani 1 1 d . . . . .
N4 N 0.5111(5) 0.4571(2) 0.6620(8) 0.0966(19) Uani 1 1 d . . . . .
N5 N 0.7775(4) 0.08235(17) 0.8752(6) 0.0559(11) Uani 1 1 d . . . . .
C1 C 0.1199(5) 0.1242(3) 0.4071(8) 0.0638(16) Uani 1 1 d . . . . .
C2 C 0.1913(5) 0.1671(2) 0.4661(7) 0.0542(14) Uani 1 1 d . . . . .
C3 C 0.3044(4) 0.1612(2) 0.5468(7) 0.0504(13) Uani 1 1 d . . . . .
C4 C 0.3556(4) 0.1126(2) 0.5766(8) 0.0588(15) Uani 1 1 d . . . . .
C5 C 0.2057(5) 0.4437(2) 0.4365(8) 0.0622(15) Uani 1 1 d . . . . .
C6 C 0.2510(4) 0.3934(2) 0.4911(7) 0.0515(13) Uani 1 1 d . . . . .
C7 C 0.3615(4) 0.3865(2) 0.5792(7) 0.0482(13) Uani 1 1 d . . . . .
C8 C 0.4410(5) 0.4273(2) 0.6235(8) 0.0621(15) Uani 1 1 d . . . . .
C9 C 0.8735(5) 0.0766(3) 0.8200(11) 0.082(2) Uani 1 1 d . . . . .
H9 H 0.939347 0.089939 0.892046 0.098 Uiso 1 1 calc R U . . .
C10 C 0.8775(8) 0.0518(3) 0.6623(14) 0.109(3) Uani 1 1 d . . . . .
H10 H 0.946042 0.047046 0.626294 0.131 Uiso 1 1 calc R U . . .
C11 C 0.7793(9) 0.0333(3) 0.5531(10) 0.097(3) Uani 1 1 d . . . . .
H11 H 0.780133 0.017178 0.440167 0.117 Uiso 1 1 calc R U . . .
C12 C 0.6822(7) 0.0390(3) 0.6129(11) 0.088(2) Uani 1 1 d . . . . .
H12 H 0.615248 0.025806 0.543637 0.105 Uiso 1 1 calc R U . . .
C13 C 0.6831(5) 0.0638(2) 0.7732(9) 0.0684(17) Uani 1 1 d . . . . .
H13 H 0.615854 0.068054 0.813768 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7753(5) 0.1100(2) 1.0537(8) 0.0744(18) Uani 1 1 d . . . . .
H14A H 0.710308 0.098510 1.100985 0.089 Uiso 1 1 calc R U . . .
H14B H 0.842333 0.101005 1.144916 0.089 Uiso 1 1 calc R U . . .
C15 C 0.7701(4) 0.1672(2) 1.0293(7) 0.0524(13) Uani 1 1 d . . . . .
C16 C 0.6695(5) 0.1915(3) 0.9547(8) 0.0700(18) Uani 1 1 d . . . . .
H16 H 0.605106 0.171912 0.911777 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6647(5) 0.2440(3) 0.9439(8) 0.0746(19) Uani 1 1 d . . . . .
H17 H 0.596749 0.260299 0.894509 0.090 Uiso 1 1 calc R U . . .
C18 C 0.7581(5) 0.2725(2) 1.0046(8) 0.0632(16) Uani 1 1 d . . . . .
C19 C 0.8586(5) 0.2499(2) 1.0766(8) 0.0683(17) Uani 1 1 d . . . . .
H19 H 0.922732 0.269855 1.116976 0.082 Uiso 1 1 calc R U . . .
C20 C 0.8636(5) 0.1974(2) 1.0886(8) 0.0667(16) Uani 1 1 d . . . . .
H20 H 0.932052 0.181634 1.138281 0.080 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.141(2) . ?
Ni1 S2 2.134(2) . ?
Ni1 S3 2.146(2) . ?
Ni1 S4 2.134(2) . ?
S1 C2 1.701(6) . ?
S2 C3 1.693(6) . ?
S3 C6 1.709(6) . ?
S4 C7 1.701(5) . ?
F1 C18 1.496(7) . ?
N1 C1 1.142(7) . ?
N2 C4 1.135(7) . ?
N3 C5 1.124(7) . ?
N4 C8 1.139(7) . ?
N5 C9 1.317(7) . ?
N5 C13 1.324(6) . ?
N5 C14 1.498(7) . ?
C1 C2 1.422(8) . ?
C2 C3 1.387(7) . ?
C3 C4 1.399(7) . ?
C5 C6 1.437(8) . ?
C6 C7 1.375(7) . ?
C7 C8 1.422(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.333(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.346(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.339(9) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.492(8) . ?
C15 C16 1.382(7) . ?
C15 C20 1.373(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.348(8) . ?
C18 C19 1.358(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.361(8) . ?
C20 H20 0.9300 . ?

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 S3 88.56(9) . . ?
S2 Ni1 S1 92.61(9) . . ?
S2 Ni1 S3 177.50(7) . . ?
S2 Ni1 S4 85.92(9) . . ?
S4 Ni1 S1 178.52(6) . . ?
S4 Ni1 S3 92.89(9) . . ?
C2 S1 Ni1 102.9(2) . . ?
C3 S2 Ni1 104.17(19) . . ?
C6 S3 Ni1 102.6(2) . . ?
C7 S4 Ni1 103.54(19) . . ?
C9 N5 C13 120.1(6) . . ?
C9 N5 C14 119.9(5) . . ?
C13 N5 C14 120.1(5) . . ?
N1 C1 C2 179.3(7) . . ?
C1 C2 S1 116.8(4) . . ?
C3 C2 S1 121.1(4) . . ?
C3 C2 C1 122.1(5) . . ?
C2 C3 S2 119.2(4) . . ?
C2 C3 C4 122.3(5) . . ?
C4 C3 S2 118.5(4) . . ?
N2 C4 C3 176.8(6) . . ?
N3 C5 C6 178.1(7) . . ?
C5 C6 S3 117.2(4) . . ?
C7 C6 S3 120.9(4) . . ?
C7 C6 C5 121.9(5) . . ?
C6 C7 S4 120.0(4) . . ?
C6 C7 C8 124.2(5) . . ?
C8 C7 S4 115.7(4) . . ?
N4 C8 C7 174.7(7) . . ?
N5 C9 H9 119.6 . . ?
N5 C9 C10 120.9(7) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.5(7) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.8(7) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(7) . . ?
C13 C12 H12 120.4 . . ?
N5 C13 C12 121.5(6) . . ?
N5 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
N5 C14 H14A 109.2 . . ?
N5 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 N5 112.1(5) . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C16 C15 C14 120.7(5) . . ?
C20 C15 C14 121.0(5) . . ?
C20 C15 C16 118.2(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(6) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(6) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 F1 118.8(5) . . ?
C17 C18 C19 121.4(6) . . ?
C19 C18 F1 119.8(6) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.6(6) . . ?
C20 C19 H19 120.7 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.6(6) . . ?
C19 C20 H20 119.2 . . ?

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 C2 C1 -178.6(4) . . . . ?
Ni1 S1 C2 C3 -1.0(5) . . . . ?
Ni1 S2 C3 C2 -2.3(4) . . . . ?
Ni1 S2 C3 C4 177.9(4) . . . . ?
Ni1 S3 C6 C5 176.3(4) . . . . ?
Ni1 S3 C6 C7 -2.5(4) . . . . ?
Ni1 S4 C7 C6 1.7(4) . . . . ?
Ni1 S4 C7 C8 -176.2(4) . . . . ?
S1 C2 C3 S2 2.3(6) . . . . ?
S1 C2 C3 C4 -177.9(4) . . . . ?
S3 C6 C7 S4 0.6(6) . . . . ?
S3 C6 C7 C8 178.2(4) . . . . ?
F1 C18 C19 C20 177.8(5) . . . . ?
N5 C9 C10 C11 1.8(12) . . . . ?
N5 C14 C15 C16 79.1(7) . . . . ?
N5 C14 C15 C20 -104.2(6) . . . . ?
C1 C2 C3 S2 179.8(4) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
C5 C6 C7 S4 -178.1(4) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
C9 N5 C13 C12 -0.1(9) . . . . ?
C9 N5 C14 C15 83.3(7) . . . . ?
C9 C10 C11 C12 -2.7(12) . . . . ?
C10 C11 C12 C13 2.1(12) . . . . ?
C11 C12 C13 N5 -0.7(11) . . . . ?
C13 N5 C9 C10 -0.4(10) . . . . ?
C13 N5 C14 C15 -96.7(6) . . . . ?
C14 N5 C9 C10 179.5(6) . . . . ?
C14 N5 C13 C12 179.9(6) . . . . ?
C14 C15 C16 C17 175.9(6) . . . . ?
C14 C15 C20 C19 -176.3(6) . . . . ?
C15 C16 C17 C18 0.5(10) . . . . ?
C16 C15 C20 C19 0.5(9) . . . . ?
C16 C17 C18 F1 -178.2(5) . . . . ?
C16 C17 C18 C19 0.3(10) . . . . ?
C17 C18 C19 C20 -0.6(9) . . . . ?
C18 C19 C20 C15 0.2(9) . . . . ?
C20 C15 C16 C17 -0.9(9) . . . . ?

_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_1_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2210277'
loop_
_audit_author_name
_audit_author_address
'Wanwan Yao'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 N4 Ni S4, C12 H11 Cl0.462 F0.538 N'
_chemical_formula_sum            'C20 H11 Cl0.46 F0.54 N5 Ni S4'
_chemical_formula_weight         534.89
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   12.1259(5)
_cell_length_b                   26.0819(12)
_cell_length_c                   7.3514(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.2104(12)
_cell_angle_gamma                90
_cell_volume                     2272.40(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7801
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.746
_shelx_estimated_absorpt_T_min   0.659
_exptl_absorpt_coefficient_mu    1.298
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.8902.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1083
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1442
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            84267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.322
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             4232
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.044
_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)+(0.0407P)²+0.7369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{F1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C19(H19),
 C20(H20)
;
_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
Ni1 Ni 0.27058(3) 0.27662(2) 0.53236(6) 0.05635(15) Uani 1 1 d . . . . .
S1 S 0.13297(7) 0.22603(3) 0.42720(12) 0.0633(2) Uani 1 1 d . . . . .
S2 S 0.38411(7) 0.21407(3) 0.61611(13) 0.0639(2) Uani 1 1 d . . . . .
S3 S 0.16199(7) 0.34076(4) 0.43963(12) 0.0636(2) Uani 1 1 d . . . . .
S4 S 0.41151(7) 0.32531(4) 0.63831(13) 0.0653(3) Uani 1 1 d . . . . .
F1 F 0.74593(18) 0.33101(6) 0.9963(2) 0.1142(10) Uani 0.538(10) 1 d . . P . .
Cl1 Cl 0.74593(18) 0.33101(6) 0.9963(2) 0.1142(10) Uani 0.462(10) 1 d . . P . .
N1 N 0.0620(3) 0.08892(14) 0.3614(5) 0.0989(11) Uani 1 1 d . . . . .
N2 N 0.4027(3) 0.07420(14) 0.6056(5) 0.0966(11) Uani 1 1 d . . . . .
N3 N 0.1687(3) 0.48130(14) 0.3859(5) 0.0991(11) Uani 1 1 d . . . . .
N4 N 0.5110(4) 0.45618(14) 0.6616(6) 0.1094(13) Uani 1 1 d . . . . .
N5 N 0.7781(2) 0.08102(11) 0.8762(4) 0.0664(8) Uani 1 1 d . . . . .
C1 C 0.1205(3) 0.12283(14) 0.4075(5) 0.0661(9) Uani 1 1 d . . . . .
C2 C 0.1911(3) 0.16616(12) 0.4641(4) 0.0562(8) Uani 1 1 d . . . . .
C3 C 0.3019(3) 0.16149(12) 0.5468(4) 0.0549(8) Uani 1 1 d . . . . .
C4 C 0.3568(3) 0.11237(15) 0.5790(5) 0.0679(9) Uani 1 1 d . . . . .
C5 C 0.2070(3) 0.44240(16) 0.4371(5) 0.0734(10) Uani 1 1 d . . . . .
C6 C 0.2518(3) 0.39260(13) 0.4927(4) 0.0603(9) Uani 1 1 d . . . . .
C7 C 0.3607(3) 0.38542(13) 0.5793(4) 0.0609(9) Uani 1 1 d . . . . .
C8 C 0.4417(4) 0.42610(16) 0.6236(5) 0.0758(10) Uani 1 1 d . . . . .
C9 C 0.8752(4) 0.07478(17) 0.8234(7) 0.0955(13) Uani 1 1 d . . . . .
H9 H 0.941548 0.087219 0.897606 0.115 Uiso 1 1 calc R U . . .
C10 C 0.8783(5) 0.05046(18) 0.6623(9) 0.1151(18) Uani 1 1 d . . . . .
H10 H 0.946366 0.046377 0.624840 0.138 Uiso 1 1 calc R U . . .
C11 C 0.7796(6) 0.03176(17) 0.5541(7) 0.1042(16) Uani 1 1 d . . . . .
H11 H 0.779950 0.015116 0.442344 0.125 Uiso 1 1 calc R U . . .
C12 C 0.6823(4) 0.03808(17) 0.6137(7) 0.0992(14) Uani 1 1 d . . . . .
H12 H 0.614882 0.025525 0.543139 0.119 Uiso 1 1 calc R U . . .
C13 C 0.6831(3) 0.06258(14) 0.7752(6) 0.0780(11) Uani 1 1 d . . . . .
H13 H 0.616126 0.066575 0.816168 0.094 Uiso 1 1 calc R U . . .
C14 C 0.7767(3) 0.10828(15) 1.0537(5) 0.0800(11) Uani 1 1 d . . . . .
H14A H 0.844400 0.099617 1.144726 0.096 Uiso 1 1 calc R U . . .
H14B H 0.712268 0.096648 1.101513 0.096 Uiso 1 1 calc R U . . .
C15 C 0.7702(3) 0.16586(14) 1.0296(4) 0.0636(9) Uani 1 1 d . . . . .
C16 C 0.6701(3) 0.18983(18) 0.9579(5) 0.0810(11) Uani 1 1 d . . . . .
H16 H 0.605726 0.170142 0.916455 0.097 Uiso 1 1 calc R U . . .
C17 C 0.6624(4) 0.24221(19) 0.9456(5) 0.0870(12) Uani 1 1 d . . . . .
H17 H 0.593845 0.258064 0.896905 0.104 Uiso 1 1 calc R U . . .
C18 C 0.7572(4) 0.27045(16) 1.0060(5) 0.0740(11) Uani 1 1 d . . . . .
C19 C 0.8587(3) 0.24851(17) 1.0753(5) 0.0815(11) Uani 1 1 d . . . . .
H19 H 0.922939 0.268502 1.113676 0.098 Uiso 1 1 calc R U . . .
C20 C 0.8644(3) 0.19553(16) 1.0873(5) 0.0781(11) Uani 1 1 d . . . . .
H20 H 0.933218 0.179838 1.135407 0.094 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1395(9) . ?
Ni1 S2 2.1394(9) . ?
Ni1 S3 2.1488(9) . ?
Ni1 S4 2.1394(10) . ?
S1 C2 1.711(3) . ?
S2 C3 1.709(3) . ?
S3 C6 1.728(4) . ?
S4 C7 1.707(3) . ?
F1 C18 1.586(4) . ?
N1 C1 1.140(4) . ?
N2 C4 1.137(4) . ?
N3 C5 1.146(5) . ?
N4 C8 1.139(5) . ?
N5 C9 1.325(5) . ?
N5 C13 1.322(4) . ?
N5 C14 1.490(4) . ?
C1 C2 1.425(5) . ?
C2 C3 1.358(4) . ?
C3 C4 1.440(5) . ?
C5 C6 1.434(5) . ?
C6 C7 1.352(4) . ?
C7 C8 1.436(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.350(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.353(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.347(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.512(5) . ?
C15 C16 1.368(5) . ?
C15 C20 1.370(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.358(5) . ?
C18 C19 1.355(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(5) . ?
C20 H20 0.9300 . ?

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 S3 89.24(4) . . ?
S2 Ni1 S1 92.23(4) . . ?
S2 Ni1 S3 177.17(4) . . ?
S4 Ni1 S1 178.31(4) . . ?
S4 Ni1 S2 86.11(4) . . ?
S4 Ni1 S3 92.41(4) . . ?
C2 S1 Ni1 104.00(12) . . ?
C3 S2 Ni1 103.10(12) . . ?
C6 S3 Ni1 102.88(12) . . ?
C7 S4 Ni1 103.60(12) . . ?
C9 N5 C14 119.4(3) . . ?
C13 N5 C9 120.9(4) . . ?
C13 N5 C14 119.7(3) . . ?
N1 C1 C2 178.4(4) . . ?
C1 C2 S1 118.4(3) . . ?
C3 C2 S1 119.2(3) . . ?
C3 C2 C1 122.4(3) . . ?
C2 C3 S2 121.4(3) . . ?
C2 C3 C4 122.2(3) . . ?
C4 C3 S2 116.4(3) . . ?
N2 C4 C3 178.4(4) . . ?
N3 C5 C6 177.1(4) . . ?
C5 C6 S3 117.5(3) . . ?
C7 C6 S3 120.3(3) . . ?
C7 C6 C5 122.2(3) . . ?
C6 C7 S4 120.7(3) . . ?
C6 C7 C8 123.9(3) . . ?
C8 C7 S4 115.3(3) . . ?
N4 C8 C7 175.9(5) . . ?
N5 C9 H9 119.8 . . ?
N5 C9 C10 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(5) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
N5 C13 C12 120.7(4) . . ?
N5 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N5 C14 H14A 109.1 . . ?
N5 C14 H14B 109.1 . . ?
N5 C14 C15 112.4(3) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 C20 118.3(4) . . ?
C20 C15 C14 120.4(3) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.5(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 F1 117.8(4) . . ?
C19 C18 F1 120.0(4) . . ?
C19 C18 C17 122.2(4) . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.3(4) . . ?
C20 C19 H19 120.9 . . ?
C15 C20 C19 121.1(4) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?

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 S1 C2 C1 -179.7(2) . . . . ?
Ni1 S1 C2 C3 0.8(3) . . . . ?
Ni1 S2 C3 C2 -1.4(3) . . . . ?
Ni1 S2 C3 C4 177.9(2) . . . . ?
Ni1 S3 C6 C5 176.1(2) . . . . ?
Ni1 S3 C6 C7 -2.3(3) . . . . ?
Ni1 S4 C7 C6 2.5(3) . . . . ?
Ni1 S4 C7 C8 -175.9(2) . . . . ?
S1 C2 C3 S2 0.4(4) . . . . ?
S1 C2 C3 C4 -178.8(2) . . . . ?
S3 C6 C7 S4 -0.1(4) . . . . ?
S3 C6 C7 C8 178.1(3) . . . . ?
F1 C18 C19 C20 177.8(3) . . . . ?
N5 C9 C10 C11 -0.6(8) . . . . ?
N5 C14 C15 C16 79.6(4) . . . . ?
N5 C14 C15 C20 -103.4(4) . . . . ?
C1 C2 C3 S2 -179.1(2) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C5 C6 C7 S4 -178.5(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C9 N5 C13 C12 -1.7(6) . . . . ?
C9 N5 C14 C15 84.8(4) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?
C11 C12 C13 N5 0.6(7) . . . . ?
C13 N5 C9 C10 1.7(6) . . . . ?
C13 N5 C14 C15 -96.4(4) . . . . ?
C14 N5 C9 C10 -179.6(4) . . . . ?
C14 N5 C13 C12 179.6(4) . . . . ?
C14 C15 C16 C17 176.2(3) . . . . ?
C14 C15 C20 C19 -176.6(3) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C15 C20 C19 0.6(5) . . . . ?
C16 C17 C18 F1 -178.2(3) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C18 C19 C20 -1.3(6) . . . . ?
C18 C19 C20 C15 0.5(6) . . . . ?
C20 C15 C16 C17 -0.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
