# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_myd
_database_code_depnum_ccdc_archive 'CCDC 1861574'
_audit_update_record             
;
2018-08-11 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        NiSPh
_chemical_formula_moiety         
'C8.69 H14.25 N1.18 Ni0.59 S1.18, 0.41(C14 H22 N2 Ni1 S2)'
_chemical_formula_sum            'C14.40 H23.21 N2 Ni S2'
_chemical_formula_weight         347.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.6130(7)
_cell_length_b                   10.3609(7)
_cell_length_c                   15.3479(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.156(3)
_cell_angle_gamma                90
_cell_volume                     1526.32(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.51
_cell_measurement_theta_min      4.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.286
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4486
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1139 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.5953.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             735
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28502
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.504
_diffrn_reflns_theta_min         5.153
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD APEX2 area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2856
_reflns_number_total             3013
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     417
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.055
_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)+(0.0088P)²+9.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C9_1, C10_1, C11_1, C12_1, C13_1, C14_1
 C9_2, C10_2, C11_2, C12_2, C13_2, C14_2
 with sigma of 0.1
3. Rigid bond restraints
 Ni1_1, S1_1, S2_1, N1_1, N2_1, C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1,
  C9_1, C10_1, C11_1, C12_1, C13_1, C14_1
 Ni1_2, S1_2, S2_2, N1_2, N2_2, C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2,
  C9_2, C10_2, C11_2, C12_2, C13_2, C14_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Uiso/Uaniso restraints and constraints
Ni1_1 \\sim S1_1 \\sim S2_1 \\sim N1_1 \\sim N2_1 \\sim C1_1 \\sim C2_1 \\sim
C3_1 \\sim C4_1 \\sim C5_1 \\sim C6_1 \\sim C7_1 \\sim C8_1 \\sim C9_1 \\sim
C10_1 \\sim C11_1 \\sim C12_1 \\sim C13_1 \\sim C14_1 \\sim Ni1_2 \\sim S1_2
\\sim S2_2 \\sim N1_2 \\sim N2_2 \\sim C1_2 \\sim C2_2 \\sim C3_2 \\sim C4_2
\\sim C5_2 \\sim C6_2 \\sim C7_2 \\sim C8_2 \\sim C9_2 \\sim C10_2 \\sim C11_2
\\sim C12_2 \\sim C13_2 \\sim C14_2: within 2A with sigma of 0.004 and sigma
for terminal atoms of 0.01
5. Same fragment restrains
{Ni1_2, S1_2, S2_2, N1_2, N2_2, C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2,
C9_2, C10_2, C11_2, C12_2, C13_2, C14_2}
as
{Ni1_1, S1_1, S2_1, N1_1, N2_1, C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1,
C9_1, C10_1, C11_1, C12_1, C13_1, C14_1} sigma for 1-2: 0.005 1-3: 0.04
6. Others
 Sof(Ni1)=Sof(S1)=Sof(S2)=Sof(N1)=Sof(N2)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=
 Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=1-FVAR(1)
 Sof(Ni1)=Sof(S1)=Sof(S2)=Sof(N1)=Sof(N2)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=
 Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C9)=
 Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(H14)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B),
 C6(H6A,H6B), C7(H7A,H7B)
7.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14)
7.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1_1 Ni 0.4247(3) 0.2004(2) 0.50276(15) 0.0246(5) Uani 0.592(5) 1 d D U P A 1
S1_1 S 0.5721(6) 0.2445(10) 0.4064(3) 0.0277(8) Uani 0.592(5) 1 d D U P A 1
S2_1 S 0.2871(7) 0.1206(9) 0.3983(5) 0.0309(11) Uani 0.592(5) 1 d D U P A 1
N1_1 N 0.5590(7) 0.2531(5) 0.5950(3) 0.0274(10) Uani 0.592(5) 1 d D U P A 1
N2_1 N 0.3024(7) 0.1869(6) 0.6025(3) 0.0320(10) Uani 0.592(5) 1 d D U P A 1
C1_1 C 0.7154(8) 0.3071(8) 0.4786(5) 0.0306(13) Uani 0.592(5) 1 d D U P A 1
H1A_1 H 0.806272 0.287177 0.454307 0.037 Uiso 0.592(5) 1 calc R . P A 1
H1B_1 H 0.707329 0.401856 0.484752 0.037 Uiso 0.592(5) 1 calc R . P A 1
C2_1 C 0.7048(7) 0.2425(7) 0.5658(4) 0.0303(12) Uani 0.592(5) 1 d D U P A 1
H2A_1 H 0.770232 0.283944 0.609380 0.036 Uiso 0.592(5) 1 calc R . P A 1
H2B_1 H 0.730944 0.150405 0.561293 0.036 Uiso 0.592(5) 1 calc R . P A 1
C3_1 C 0.5257(8) 0.3885(6) 0.6175(4) 0.0301(12) Uani 0.592(5) 1 d D U P A 1
H3A_1 H 0.516528 0.440660 0.563403 0.036 Uiso 0.592(5) 1 calc R . P A 1
H3B_1 H 0.603044 0.425007 0.654998 0.036 Uiso 0.592(5) 1 calc R . P A 1
C4_1 C 0.3908(9) 0.3969(9) 0.6650(6) 0.0345(14) Uani 0.592(5) 1 d D U P A 1
H4A_1 H 0.409288 0.364339 0.725193 0.041 Uiso 0.592(5) 1 calc R . P A 1
H4B_1 H 0.364601 0.488985 0.669394 0.041 Uiso 0.592(5) 1 calc R . P A 1
C5_1 C 0.2684(10) 0.3247(8) 0.6246(6) 0.0343(14) Uani 0.592(5) 1 d D U P A 1
H5A_1 H 0.234457 0.369821 0.570707 0.041 Uiso 0.592(5) 1 calc R . P A 1
H5B_1 H 0.192295 0.325245 0.665487 0.041 Uiso 0.592(5) 1 calc R . P A 1
C6_1 C 0.5400(9) 0.1668(9) 0.6723(5) 0.0310(13) Uani 0.592(5) 1 d D U P A 1
H6A_1 H 0.568095 0.213527 0.726685 0.037 Uiso 0.592(5) 1 calc R . P A 1
H6B_1 H 0.600172 0.089743 0.668411 0.037 Uiso 0.592(5) 1 calc R . P A 1
C7_1 C 0.3884(9) 0.1250(9) 0.6747(5) 0.0349(14) Uani 0.592(5) 1 d D U P A 1
H7A_1 H 0.382187 0.030010 0.669061 0.042 Uiso 0.592(5) 1 calc R . P A 1
H7B_1 H 0.351967 0.149651 0.731461 0.042 Uiso 0.592(5) 1 calc R . P A 1
C8_1 C 0.1687(7) 0.1162(8) 0.5906(5) 0.0794(19) Uani 1 1 d D U . A 1
H8A_1 H 0.107003 0.161714 0.547953 0.119 Uiso 1 1 calc GR . . A 1
H8B_1 H 0.124370 0.111422 0.646540 0.119 Uiso 1 1 calc GR . . A 1
H8C_1 H 0.186315 0.028761 0.569571 0.119 Uiso 1 1 calc GR . . A 1
C9_1 C 0.1486(10) 0.2259(11) 0.3711(7) 0.0271(14) Uani 0.592(5) 1 d D U P A 1
C10_1 C 0.0227(10) 0.1740(12) 0.3384(6) 0.0305(17) Uani 0.592(5) 1 d D U P A 1
H10_1 H 0.011752 0.082927 0.335900 0.037 Uiso 0.592(5) 1 calc R . P A 1
C11_1 C -0.0866(11) 0.2522(11) 0.3095(6) 0.0360(18) Uani 0.592(5) 1 d D U P A 1
H11_1 H -0.171422 0.214641 0.287283 0.043 Uiso 0.592(5) 1 calc R . P A 1
C12_1 C -0.0729(12) 0.3848(11) 0.3129(7) 0.0368(19) Uani 0.592(5) 1 d D U P A 1
H12_1 H -0.146066 0.438867 0.290124 0.044 Uiso 0.592(5) 1 calc R . P A 1
C13_1 C 0.0485(13) 0.4381(12) 0.3498(7) 0.0324(19) Uani 0.592(5) 1 d D U P A 1
H13_1 H 0.056358 0.529124 0.355284 0.039 Uiso 0.592(5) 1 calc R . P A 1
C14_1 C 0.1595(13) 0.3598(11) 0.3789(8) 0.0284(18) Uani 0.592(5) 1 d D U P A 1
H14_1 H 0.242426 0.397487 0.404031 0.034 Uiso 0.592(5) 1 calc R . P A 1
Ni1_2 Ni 0.3798(3) 0.2221(3) 0.4978(2) 0.0174(6) Uani 0.408(5) 1 d D U P A 2
S1_2 S 0.5552(8) 0.2363(16) 0.4171(4) 0.0286(13) Uani 0.408(5) 1 d D U P A 2
S2_2 S 0.2618(10) 0.1271(12) 0.3902(7) 0.0225(12) Uani 0.408(5) 1 d D U P A 2
N1_2 N 0.4932(8) 0.2815(6) 0.5984(4) 0.0195(11) Uani 0.408(5) 1 d D U P A 2
N2_2 N 0.2386(7) 0.2084(7) 0.5872(4) 0.0192(11) Uani 0.408(5) 1 d D U P A 2
C1_2 C 0.6910(10) 0.2749(11) 0.5022(7) 0.0286(16) Uani 0.408(5) 1 d D U P A 2
H1A_2 H 0.733194 0.194642 0.526708 0.034 Uiso 0.408(5) 1 calc R . P A 2
H1B_2 H 0.765359 0.327470 0.477558 0.034 Uiso 0.408(5) 1 calc R . P A 2
C2_2 C 0.6217(8) 0.3493(9) 0.5720(5) 0.0245(14) Uani 0.408(5) 1 d D U P A 2
H2A_2 H 0.687481 0.359134 0.623540 0.029 Uiso 0.408(5) 1 calc R . P A 2
H2B_2 H 0.596782 0.436534 0.550041 0.029 Uiso 0.408(5) 1 calc R . P A 2
C3_2 C 0.5329(11) 0.1630(10) 0.6487(7) 0.0221(15) Uani 0.408(5) 1 d D U P A 2
H3A_2 H 0.609569 0.184058 0.692048 0.026 Uiso 0.408(5) 1 calc R . P A 2
H3B_2 H 0.567791 0.097485 0.608301 0.026 Uiso 0.408(5) 1 calc R . P A 2
C4_2 C 0.4113(10) 0.1064(12) 0.6957(6) 0.0231(16) Uani 0.408(5) 1 d D U P A 2
H4A_2 H 0.439435 0.021044 0.719699 0.028 Uiso 0.408(5) 1 calc R . P A 2
H4B_2 H 0.392073 0.163100 0.745598 0.028 Uiso 0.408(5) 1 calc R . P A 2
C5_2 C 0.2795(9) 0.0905(8) 0.6400(5) 0.0216(14) Uani 0.408(5) 1 d D U P A 2
H5A_2 H 0.202901 0.068639 0.677999 0.026 Uiso 0.408(5) 1 calc R . P A 2
H5B_2 H 0.290864 0.017040 0.599752 0.026 Uiso 0.408(5) 1 calc R . P A 2
C6_2 C 0.4085(10) 0.3697(10) 0.6522(7) 0.0228(15) Uani 0.408(5) 1 d D U P A 2
H6A_2 H 0.417563 0.459924 0.632141 0.027 Uiso 0.408(5) 1 calc R . P A 2
H6B_2 H 0.441794 0.365034 0.714339 0.027 Uiso 0.408(5) 1 calc R . P A 2
C7_2 C 0.2570(12) 0.3267(11) 0.6418(8) 0.0225(15) Uani 0.408(5) 1 d D U P A 2
H7A_2 H 0.222034 0.309665 0.700178 0.027 Uiso 0.408(5) 1 calc R . P A 2
H7B_2 H 0.200474 0.397381 0.614685 0.027 Uiso 0.408(5) 1 calc R . P A 2
C8_2 C 0.0881(8) 0.1979(10) 0.5599(6) 0.0268(19) Uani 0.408(5) 1 d D U P A 2
H8A_2 H 0.059947 0.273023 0.524366 0.040 Uiso 0.408(5) 1 calc GR . P A 2
H8B_2 H 0.033112 0.194647 0.611708 0.040 Uiso 0.408(5) 1 calc GR . P A 2
H8C_2 H 0.072210 0.118986 0.525503 0.040 Uiso 0.408(5) 1 calc GR . P A 2
C9_2 C 0.1266(14) 0.2333(15) 0.3573(9) 0.0183(16) Uani 0.408(5) 1 d D U P A 2
C10_2 C 0.0043(13) 0.1832(15) 0.3176(8) 0.0196(18) Uani 0.408(5) 1 d D U P A 2
H10_2 H -0.007565 0.092356 0.313431 0.023 Uiso 0.408(5) 1 calc R . P A 2
C11_2 C -0.0999(13) 0.2639(14) 0.2844(7) 0.0215(19) Uani 0.408(5) 1 d D U P A 2
H11_2 H -0.181934 0.227257 0.257443 0.026 Uiso 0.408(5) 1 calc R . P A 2
C12_2 C -0.0880(15) 0.3965(14) 0.2893(8) 0.0222(19) Uani 0.408(5) 1 d D U P A 2
H12_2 H -0.159898 0.451299 0.265913 0.027 Uiso 0.408(5) 1 calc R . P A 2
C13_2 C 0.0324(16) 0.4467(15) 0.3295(9) 0.021(2) Uani 0.408(5) 1 d D U P A 2
H13_2 H 0.041978 0.537620 0.334975 0.026 Uiso 0.408(5) 1 calc R . P A 2
C14_2 C 0.1399(17) 0.3673(15) 0.3623(10) 0.0190(19) Uani 0.408(5) 1 d D U P A 2
H14_2 H 0.222620 0.404473 0.388174 0.023 Uiso 0.408(5) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1_1 S1_1 2.153(3) . ?
Ni1_1 S2_1 2.184(3) . ?
Ni1_1 N1_1 1.941(5) . ?
Ni1_1 N2_1 1.986(5) . ?
S1_1 C1_1 1.838(6) . ?
S2_1 C9_1 1.754(6) . ?
N1_1 C2_1 1.499(8) . ?
N1_1 C3_1 1.485(8) . ?
N1_1 C6_1 1.504(8) . ?
N2_1 C5_1 1.507(8) . ?
N2_1 C7_1 1.491(9) . ?
N2_1 C8_1 1.482(8) . ?
C1_1 H1A_1 0.9900 . ?
C1_1 H1B_1 0.9900 . ?
C1_1 C2_1 1.505(8) . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2B_1 0.9900 . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
C3_1 C4_1 1.525(9) . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4B_1 0.9900 . ?
C4_1 C5_1 1.499(10) . ?
C5_1 H5A_1 0.9900 . ?
C5_1 H5B_1 0.9900 . ?
C6_1 H6A_1 0.9900 . ?
C6_1 H6B_1 0.9900 . ?
C6_1 C7_1 1.522(11) . ?
C7_1 H7A_1 0.9900 . ?
C7_1 H7B_1 0.9900 . ?
C8_1 H8A_1 0.9800 . ?
C8_1 H8B_1 0.9800 . ?
C8_1 H8C_1 0.9800 . ?
C9_1 C10_1 1.393(7) . ?
C9_1 C14_1 1.396(6) . ?
C10_1 H10_1 0.9500 . ?
C10_1 C11_1 1.380(8) . ?
C11_1 H11_1 0.9500 . ?
C11_1 C12_1 1.381(8) . ?
C12_1 H12_1 0.9500 . ?
C12_1 C13_1 1.384(8) . ?
C13_1 H13_1 0.9500 . ?
C13_1 C14_1 1.394(7) . ?
C14_1 H14_1 0.9500 . ?
Ni1_2 S1_2 2.152(4) . ?
Ni1_2 S2_2 2.186(3) . ?
Ni1_2 N1_2 1.940(5) . ?
Ni1_2 N2_2 1.987(5) . ?
S1_2 C1_2 1.840(6) . ?
S2_2 C9_2 1.756(6) . ?
N1_2 C2_2 1.496(8) . ?
N1_2 C3_2 1.488(8) . ?
N1_2 C6_2 1.502(8) . ?
N2_2 C5_2 1.506(8) . ?
N2_2 C7_2 1.490(9) . ?
N2_2 C8_2 1.487(8) . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1B_2 0.9900 . ?
C1_2 C2_2 1.505(9) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2B_2 0.9900 . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3B_2 0.9900 . ?
C3_2 C4_2 1.525(10) . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4B_2 0.9900 . ?
C4_2 C5_2 1.498(9) . ?
C5_2 H5A_2 0.9900 . ?
C5_2 H5B_2 0.9900 . ?
C6_2 H6A_2 0.9900 . ?
C6_2 H6B_2 0.9900 . ?
C6_2 C7_2 1.523(11) . ?
C7_2 H7A_2 0.9900 . ?
C7_2 H7B_2 0.9900 . ?
C8_2 H8A_2 0.9800 . ?
C8_2 H8B_2 0.9800 . ?
C8_2 H8C_2 0.9800 . ?
C9_2 C10_2 1.394(7) . ?
C9_2 C14_2 1.396(7) . ?
C10_2 H10_2 0.9500 . ?
C10_2 C11_2 1.380(8) . ?
C11_2 H11_2 0.9500 . ?
C11_2 C12_2 1.380(8) . ?
C12_2 H12_2 0.9500 . ?
C12_2 C13_2 1.382(8) . ?
C13_2 H13_2 0.9500 . ?
C13_2 C14_2 1.393(8) . ?
C14_2 H14_2 0.9500 . ?

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_1 Ni1_1 S2_1 88.4(3) . . ?
N1_1 Ni1_1 S1_1 90.3(2) . . ?
N1_1 Ni1_1 S2_1 173.5(3) . . ?
N1_1 Ni1_1 N2_1 81.7(3) . . ?
N2_1 Ni1_1 S1_1 169.9(3) . . ?
N2_1 Ni1_1 S2_1 100.3(3) . . ?
C1_1 S1_1 Ni1_1 99.2(3) . . ?
C9_1 S2_1 Ni1_1 111.2(3) . . ?
C2_1 N1_1 Ni1_1 110.9(4) . . ?
C3_1 N1_1 Ni1_1 107.0(4) . . ?
C3_1 N1_1 C2_1 110.8(5) . . ?
C3_1 N1_1 C6_1 110.0(6) . . ?
C6_1 N1_1 Ni1_1 107.7(5) . . ?
C6_1 N1_1 C2_1 110.4(6) . . ?
C5_1 N2_1 Ni1_1 104.6(4) . . ?
C7_1 N2_1 Ni1_1 106.0(5) . . ?
C7_1 N2_1 C5_1 111.0(7) . . ?
C8_1 N2_1 Ni1_1 119.1(4) . . ?
C8_1 N2_1 C5_1 107.4(6) . . ?
C8_1 N2_1 C7_1 108.7(6) . . ?
S1_1 C1_1 H1A_1 110.3 . . ?
S1_1 C1_1 H1B_1 110.3 . . ?
H1A_1 C1_1 H1B_1 108.5 . . ?
C2_1 C1_1 S1_1 107.1(6) . . ?
C2_1 C1_1 H1A_1 110.3 . . ?
C2_1 C1_1 H1B_1 110.3 . . ?
N1_1 C2_1 H2A_1 109.6 . . ?
N1_1 C2_1 H2B_1 109.6 . . ?
C1_1 C2_1 N1_1 110.1(5) . . ?
C1_1 C2_1 H2A_1 109.6 . . ?
C1_1 C2_1 H2B_1 109.6 . . ?
H2A_1 C2_1 H2B_1 108.2 . . ?
N1_1 C3_1 H3A_1 109.4 . . ?
N1_1 C3_1 H3B_1 109.4 . . ?
N1_1 C3_1 C4_1 111.4(6) . . ?
H3A_1 C3_1 H3B_1 108.0 . . ?
C4_1 C3_1 H3A_1 109.4 . . ?
C4_1 C3_1 H3B_1 109.4 . . ?
C3_1 C4_1 H4A_1 108.2 . . ?
C3_1 C4_1 H4B_1 108.2 . . ?
H4A_1 C4_1 H4B_1 107.4 . . ?
C5_1 C4_1 C3_1 116.2(7) . . ?
C5_1 C4_1 H4A_1 108.2 . . ?
C5_1 C4_1 H4B_1 108.2 . . ?
N2_1 C5_1 H5A_1 109.0 . . ?
N2_1 C5_1 H5B_1 109.0 . . ?
C4_1 C5_1 N2_1 113.0(7) . . ?
C4_1 C5_1 H5A_1 109.0 . . ?
C4_1 C5_1 H5B_1 109.0 . . ?
H5A_1 C5_1 H5B_1 107.8 . . ?
N1_1 C6_1 H6A_1 109.6 . . ?
N1_1 C6_1 H6B_1 109.6 . . ?
N1_1 C6_1 C7_1 110.3(6) . . ?
H6A_1 C6_1 H6B_1 108.1 . . ?
C7_1 C6_1 H6A_1 109.6 . . ?
C7_1 C6_1 H6B_1 109.6 . . ?
N2_1 C7_1 C6_1 110.6(6) . . ?
N2_1 C7_1 H7A_1 109.5 . . ?
N2_1 C7_1 H7B_1 109.5 . . ?
C6_1 C7_1 H7A_1 109.5 . . ?
C6_1 C7_1 H7B_1 109.5 . . ?
H7A_1 C7_1 H7B_1 108.1 . . ?
N2_1 C8_1 H8A_1 109.5 . . ?
N2_1 C8_1 H8B_1 109.5 . . ?
N2_1 C8_1 H8C_1 109.5 . . ?
H8A_1 C8_1 H8B_1 109.5 . . ?
H8A_1 C8_1 H8C_1 109.5 . . ?
H8B_1 C8_1 H8C_1 109.5 . . ?
C10_1 C9_1 S2_1 118.6(5) . . ?
C10_1 C9_1 C14_1 118.3(7) . . ?
C14_1 C9_1 S2_1 123.0(6) . . ?
C9_1 C10_1 H10_1 119.3 . . ?
C11_1 C10_1 C9_1 121.3(7) . . ?
C11_1 C10_1 H10_1 119.3 . . ?
C10_1 C11_1 H11_1 119.9 . . ?
C10_1 C11_1 C12_1 120.2(8) . . ?
C12_1 C11_1 H11_1 119.9 . . ?
C11_1 C12_1 H12_1 120.4 . . ?
C11_1 C12_1 C13_1 119.2(8) . . ?
C13_1 C12_1 H12_1 120.4 . . ?
C12_1 C13_1 H13_1 119.6 . . ?
C12_1 C13_1 C14_1 120.9(8) . . ?
C14_1 C13_1 H13_1 119.6 . . ?
C9_1 C14_1 C13_1 119.9(7) . . ?
C9_1 C14_1 H14_1 120.1 . . ?
C13_1 C14_1 H14_1 120.1 . . ?
S1_2 Ni1_2 S2_2 89.2(4) . . ?
N1_2 Ni1_2 S1_2 90.7(3) . . ?
N1_2 Ni1_2 S2_2 171.7(4) . . ?
N1_2 Ni1_2 N2_2 81.3(3) . . ?
N2_2 Ni1_2 S1_2 171.5(3) . . ?
N2_2 Ni1_2 S2_2 98.2(4) . . ?
C1_2 S1_2 Ni1_2 98.8(4) . . ?
C9_2 S2_2 Ni1_2 106.3(4) . . ?
C2_2 N1_2 Ni1_2 111.7(5) . . ?
C2_2 N1_2 C3_2 109.6(7) . . ?
C2_2 N1_2 C6_2 110.1(6) . . ?
C3_2 N1_2 Ni1_2 105.5(5) . . ?
C6_2 N1_2 Ni1_2 109.4(6) . . ?
C6_2 N1_2 C3_2 110.4(8) . . ?
C5_2 N2_2 Ni1_2 105.2(5) . . ?
C7_2 N2_2 Ni1_2 105.4(6) . . ?
C7_2 N2_2 C5_2 110.2(8) . . ?
C7_2 N2_2 C8_2 107.6(7) . . ?
C8_2 N2_2 Ni1_2 120.1(5) . . ?
C8_2 N2_2 C5_2 108.3(6) . . ?
S1_2 C1_2 H1A_2 110.3 . . ?
S1_2 C1_2 H1B_2 110.3 . . ?
H1A_2 C1_2 H1B_2 108.6 . . ?
C2_2 C1_2 S1_2 107.0(7) . . ?
C2_2 C1_2 H1A_2 110.3 . . ?
C2_2 C1_2 H1B_2 110.3 . . ?
N1_2 C2_2 C1_2 110.9(7) . . ?
N1_2 C2_2 H2A_2 109.5 . . ?
N1_2 C2_2 H2B_2 109.5 . . ?
C1_2 C2_2 H2A_2 109.5 . . ?
C1_2 C2_2 H2B_2 109.5 . . ?
H2A_2 C2_2 H2B_2 108.0 . . ?
N1_2 C3_2 H3A_2 109.1 . . ?
N1_2 C3_2 H3B_2 109.1 . . ?
N1_2 C3_2 C4_2 112.4(8) . . ?
H3A_2 C3_2 H3B_2 107.9 . . ?
C4_2 C3_2 H3A_2 109.1 . . ?
C4_2 C3_2 H3B_2 109.1 . . ?
C3_2 C4_2 H4A_2 108.6 . . ?
C3_2 C4_2 H4B_2 108.6 . . ?
H4A_2 C4_2 H4B_2 107.6 . . ?
C5_2 C4_2 C3_2 114.7(8) . . ?
C5_2 C4_2 H4A_2 108.6 . . ?
C5_2 C4_2 H4B_2 108.6 . . ?
N2_2 C5_2 H5A_2 108.8 . . ?
N2_2 C5_2 H5B_2 108.8 . . ?
C4_2 C5_2 N2_2 113.9(8) . . ?
C4_2 C5_2 H5A_2 108.8 . . ?
C4_2 C5_2 H5B_2 108.8 . . ?
H5A_2 C5_2 H5B_2 107.7 . . ?
N1_2 C6_2 H6A_2 110.1 . . ?
N1_2 C6_2 H6B_2 110.1 . . ?
N1_2 C6_2 C7_2 108.0(8) . . ?
H6A_2 C6_2 H6B_2 108.4 . . ?
C7_2 C6_2 H6A_2 110.1 . . ?
C7_2 C6_2 H6B_2 110.1 . . ?
N2_2 C7_2 C6_2 112.5(8) . . ?
N2_2 C7_2 H7A_2 109.1 . . ?
N2_2 C7_2 H7B_2 109.1 . . ?
C6_2 C7_2 H7A_2 109.1 . . ?
C6_2 C7_2 H7B_2 109.1 . . ?
H7A_2 C7_2 H7B_2 107.8 . . ?
N2_2 C8_2 H8A_2 109.5 . . ?
N2_2 C8_2 H8B_2 109.5 . . ?
N2_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C10_2 C9_2 S2_2 119.1(7) . . ?
C14_2 C9_2 S2_2 122.9(7) . . ?
C14_2 C9_2 C10_2 117.9(8) . . ?
C9_2 C10_2 H10_2 119.6 . . ?
C11_2 C10_2 C9_2 120.8(8) . . ?
C11_2 C10_2 H10_2 119.6 . . ?
C10_2 C11_2 H11_2 119.1 . . ?
C12_2 C11_2 C10_2 121.8(9) . . ?
C12_2 C11_2 H11_2 119.1 . . ?
C11_2 C12_2 H12_2 121.2 . . ?
C11_2 C12_2 C13_2 117.6(9) . . ?
C13_2 C12_2 H12_2 121.2 . . ?
C12_2 C13_2 H13_2 119.2 . . ?
C12_2 C13_2 C14_2 121.7(9) . . ?
C14_2 C13_2 H13_2 119.2 . . ?
C9_2 C14_2 H14_2 119.9 . . ?
C13_2 C14_2 C9_2 120.2(9) . . ?
C13_2 C14_2 H14_2 119.9 . . ?

_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_nise
_database_code_depnum_ccdc_archive 'CCDC 1861577'
_audit_update_record             
;
2018-08-11 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2017-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 N2 Ni S Se'
_chemical_formula_sum            'C14 H22 N2 Ni S Se'
_chemical_formula_weight         388.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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                   8.3021(14)
_cell_length_b                   16.204(3)
_cell_length_c                   11.6290(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.667(10)
_cell_angle_gamma                90
_cell_volume                     1490.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.452
_cell_measurement_theta_min      4.833
_shelx_estimated_absorpt_T_max   0.592
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    5.863
_exptl_absorpt_correction_T_max  0.2775
_exptl_absorpt_correction_T_min  0.1498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1097 before and 0.0615 after correction. The Ratio of minimum to maximum transmission is 0.5398. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.697
_diffrn_reflns_theta_min         4.835
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2566
_reflns_number_total             2947
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.073
_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)+(0.0372P)²+2.2608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0809
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.53766(4) 0.44856(2) 0.21557(3) 0.02631(11) Uani 1 1 d . . . . .
Ni1 Ni 0.56112(6) 0.33691(3) 0.34301(4) 0.02167(14) Uani 1 1 d . . . . .
S1 S 0.82757(9) 0.32066(4) 0.37027(7) 0.02340(16) Uani 1 1 d . . . . .
N1 N 0.5653(3) 0.24987(15) 0.4592(2) 0.0249(5) Uani 1 1 d . . . . .
N2 N 0.3179(3) 0.33826(16) 0.3333(2) 0.0263(6) Uani 1 1 d . . . . .
C1 C 0.8718(4) 0.2469(2) 0.4948(3) 0.0294(7) Uani 1 1 d . . . . .
H1A H 0.966835 0.210617 0.492580 0.035 Uiso 1 1 calc R . . . .
H1B H 0.904975 0.276807 0.572701 0.035 Uiso 1 1 calc R . . . .
C2 C 0.7184(4) 0.1960(2) 0.4846(3) 0.0316(7) Uani 1 1 d . . . . .
H2A H 0.733081 0.165344 0.560711 0.038 Uiso 1 1 calc R . . . .
H2B H 0.703202 0.155276 0.418610 0.038 Uiso 1 1 calc R . . . .
C3 C 0.4108(4) 0.1982(2) 0.4137(3) 0.0324(7) Uani 1 1 d . . . . .
H3A H 0.380280 0.174328 0.482634 0.039 Uiso 1 1 calc R . . . .
H3B H 0.433239 0.152161 0.364653 0.039 Uiso 1 1 calc R . . . .
C4 C 0.2640(4) 0.2505(2) 0.3367(3) 0.0314(7) Uani 1 1 d . . . . .
H4A H 0.225076 0.228104 0.253602 0.038 Uiso 1 1 calc R . . . .
H4B H 0.168413 0.247794 0.370779 0.038 Uiso 1 1 calc R . . . .
C5 C 0.5635(4) 0.2958(2) 0.5700(3) 0.0297(7) Uani 1 1 d . . . . .
H5A H 0.650334 0.339784 0.586301 0.036 Uiso 1 1 calc R . . . .
H5B H 0.593714 0.257509 0.639618 0.036 Uiso 1 1 calc R . . . .
C6 C 0.3927(4) 0.3345(2) 0.5590(3) 0.0328(7) Uani 1 1 d . . . . .
H6A H 0.313830 0.290007 0.564810 0.039 Uiso 1 1 calc R . . . .
H6B H 0.405940 0.371707 0.628805 0.039 Uiso 1 1 calc R . . . .
C7 C 0.3123(4) 0.3830(2) 0.4447(3) 0.0310(7) Uani 1 1 d . . . . .
H7A H 0.193002 0.394800 0.438761 0.037 Uiso 1 1 calc R . . . .
H7B H 0.371630 0.436488 0.449373 0.037 Uiso 1 1 calc R . . . .
C8 C 0.1945(4) 0.3780(2) 0.2283(3) 0.0334(7) Uani 1 1 d . . . . .
H8A H 0.216213 0.437494 0.230145 0.050 Uiso 1 1 calc GR . . . .
H8B H 0.079612 0.368200 0.231865 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.206107 0.354549 0.153573 0.050 Uiso 1 1 calc GR . . . .
C9 C 0.7523(4) 0.49571(17) 0.2225(3) 0.0228(6) Uani 1 1 d . . . . .
C10 C 0.7882(4) 0.51285(18) 0.1143(3) 0.0250(6) Uani 1 1 d . . . . .
H10 H 0.712894 0.494550 0.039633 0.030 Uiso 1 1 calc R . . . .
C11 C 0.9321(4) 0.55612(18) 0.1158(3) 0.0272(6) Uani 1 1 d . . . . .
H11 H 0.954431 0.567825 0.042024 0.033 Uiso 1 1 calc R . . . .
C12 C 1.0442(4) 0.5826(2) 0.2235(3) 0.0319(7) Uani 1 1 d . . . . .
H12 H 1.142379 0.612858 0.223967 0.038 Uiso 1 1 calc R . . . .
C13 C 1.0116(4) 0.56443(19) 0.3316(3) 0.0304(7) Uani 1 1 d . . . . .
H13 H 1.088846 0.581637 0.406123 0.036 Uiso 1 1 calc R . . . .
C14 C 0.8678(4) 0.52161(18) 0.3308(3) 0.0259(6) Uani 1 1 d . . . . .
H14 H 0.846926 0.509562 0.404925 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Ni1 2.3092(6) . ?
Se1 C9 1.918(3) . ?
Ni1 S1 2.1535(9) . ?
Ni1 N1 1.946(2) . ?
Ni1 N2 1.988(3) . ?
S1 C1 1.827(3) . ?
N1 C2 1.496(4) . ?
N1 C3 1.489(4) . ?
N1 C5 1.493(4) . ?
N2 C4 1.495(4) . ?
N2 C7 1.497(4) . ?
N2 C8 1.482(4) . ?
C1 C2 1.492(5) . ?
C3 C4 1.530(5) . ?
C5 C6 1.520(5) . ?
C6 C7 1.514(5) . ?
C9 C10 1.406(4) . ?
C9 C14 1.395(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.383(5) . ?
C12 C13 1.395(5) . ?
C13 C14 1.378(5) . ?

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
C9 Se1 Ni1 112.88(9) . . ?
S1 Ni1 Se1 94.19(3) . . ?
N1 Ni1 Se1 173.53(8) . . ?
N1 Ni1 S1 90.46(8) . . ?
N1 Ni1 N2 81.45(10) . . ?
N2 Ni1 Se1 93.94(8) . . ?
N2 Ni1 S1 171.87(8) . . ?
C1 S1 Ni1 98.46(11) . . ?
C2 N1 Ni1 113.27(19) . . ?
C3 N1 Ni1 109.18(19) . . ?
C3 N1 C2 109.3(2) . . ?
C3 N1 C5 110.8(2) . . ?
C5 N1 Ni1 103.60(18) . . ?
C5 N1 C2 110.6(2) . . ?
C4 N2 Ni1 107.13(19) . . ?
C4 N2 C7 110.5(2) . . ?
C7 N2 Ni1 104.71(18) . . ?
C8 N2 Ni1 119.2(2) . . ?
C8 N2 C4 107.3(2) . . ?
C8 N2 C7 107.9(2) . . ?
C2 C1 S1 109.7(2) . . ?
C1 C2 N1 110.3(3) . . ?
N1 C3 C4 110.1(2) . . ?
N2 C4 C3 110.5(2) . . ?
N1 C5 C6 112.8(3) . . ?
C7 C6 C5 116.1(3) . . ?
N2 C7 C6 112.7(3) . . ?
C10 C9 Se1 119.2(2) . . ?
C14 C9 Se1 122.2(2) . . ?
C14 C9 C10 118.3(3) . . ?
C11 C10 C9 120.4(3) . . ?
C10 C11 C12 120.7(3) . . ?
C11 C12 C13 119.3(3) . . ?
C14 C13 C12 120.3(3) . . ?
C13 C14 C9 120.9(3) . . ?

_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_163_3
_database_code_depnum_ccdc_archive 'CCDC 1861890'
_audit_update_record             
;
2018-08-13 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-08-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 Fe N2 Ni O2 S Se, B F4, C1 H2 Cl2'
_chemical_formula_sum            'C21 H30 B Cl2 F4 Fe N2 Ni O2 S Se'
_chemical_formula_weight         725.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4360(15)
_cell_length_b                   11.886(3)
_cell_length_c                   12.4060(17)
_cell_angle_alpha                108.489(8)
_cell_angle_beta                 114.188(5)
_cell_angle_gamma                103.182(9)
_cell_volume                     1328.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9017
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      4.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.879
_exptl_absorpt_correction_T_max  0.2772
_exptl_absorpt_correction_T_min  0.1257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1035 before and 0.0531 after correction. The Ratio of minimum to maximum transmission is 0.4535. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             730
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40945
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.354
_diffrn_reflns_theta_min         4.308
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Micro-Source CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4910
_reflns_number_total             5209
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.235
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5209
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.020
_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)+(0.0345P)²+2.3259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1_1-C1_1 = Cl2_1-C1_1
 1.771 with sigma of 0.01
 Cl1_1-Cl2_1
 2.916 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Cl1_1 \\sim Cl2_1 \\sim C1_1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uiso(Cl1_1) = Uiso(Cl2_1) = Uiso(C1_1)
4. Rigid body (RIGU) restrains
 Cl1_1, Cl2_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl1)=Sof(Cl2)=Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C1A(H1AA,H1AB), C1(H1A,H1B)
6.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
6.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.16285(3) 0.66490(3) 0.22237(3) 0.02072(8) Uani 1 1 d . . . . .
Ni1 Ni 0.47591(4) 0.81358(4) 0.46997(4) 0.01862(11) Uani 1 1 d . . . . .
Fe1 Fe 0.12238(4) 0.71287(4) 0.39795(4) 0.01789(10) Uani 1 1 d . . . . .
S1 S 0.33612(6) 0.87996(6) 0.51974(6) 0.02015(13) Uani 1 1 d . . . . .
O1 O 0.2255(2) 0.5395(2) 0.4881(2) 0.0353(5) Uani 1 1 d . . . . .
O2 O 0.34575(18) 0.73522(18) 0.28665(18) 0.0235(4) Uani 1 1 d . . . . .
N1 N 0.6126(2) 0.8809(2) 0.6545(2) 0.0217(4) Uani 1 1 d . . . . .
N2 N 0.6227(2) 0.7693(2) 0.4470(2) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.1873(3) 0.6090(3) 0.4511(3) 0.0234(5) Uani 1 1 d . . . . .
C2 C 0.4272(3) 0.9136(3) 0.6950(3) 0.0281(6) Uani 1 1 d . . . . .
H2A H 0.403552 0.974587 0.746250 0.034 Uiso 1 1 calc R . . . .
H2B H 0.401610 0.833901 0.702431 0.034 Uiso 1 1 calc R . . . .
C3 C 0.5823(3) 0.9715(3) 0.7438(3) 0.0251(6) Uani 1 1 d . . . . .
H3A H 0.608187 1.055159 0.743974 0.030 Uiso 1 1 calc R . . . .
H3B H 0.637416 0.985151 0.834290 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7548(3) 0.9492(3) 0.6785(3) 0.0245(5) Uani 1 1 d . . . . .
H4A H 0.826733 0.947893 0.754127 0.029 Uiso 1 1 calc R . . . .
H4B H 0.773062 1.039428 0.698466 0.029 Uiso 1 1 calc R . . . .
C5 C 0.7598(3) 0.8808(3) 0.5540(3) 0.0240(5) Uani 1 1 d . . . . .
H5A H 0.782169 0.942473 0.522137 0.029 Uiso 1 1 calc R . . . .
H5B H 0.833461 0.849580 0.576667 0.029 Uiso 1 1 calc R . . . .
C6 C 0.6058(3) 0.7633(3) 0.6777(3) 0.0254(6) Uani 1 1 d . . . . .
H6A H 0.508499 0.708401 0.641759 0.030 Uiso 1 1 calc R . . . .
H6B H 0.657234 0.791353 0.772821 0.030 Uiso 1 1 calc R . . . .
C7 C 0.6677(3) 0.6845(3) 0.6129(3) 0.0279(6) Uani 1 1 d . . . . .
H7A H 0.769274 0.732401 0.664300 0.033 Uiso 1 1 calc R . . . .
H7B H 0.647167 0.603362 0.618440 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6158(3) 0.6523(3) 0.4682(3) 0.0288(6) Uani 1 1 d . . . . .
H8A H 0.672732 0.615583 0.441338 0.035 Uiso 1 1 calc R . . . .
H8B H 0.519293 0.587153 0.412584 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6095(3) 0.7406(3) 0.3164(3) 0.0285(6) Uani 1 1 d . . . . .
H9A H 0.525096 0.663774 0.247848 0.043 Uiso 1 1 calc GR . . . .
H9B H 0.689560 0.726588 0.318223 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.605287 0.812865 0.298353 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.1305(3) 0.4825(3) 0.1526(2) 0.0227(5) Uani 1 1 d . . . . .
C11 C 0.2116(3) 0.4434(3) 0.1034(3) 0.0252(6) Uani 1 1 d . . . . .
H11 H 0.284873 0.504744 0.110275 0.030 Uiso 1 1 calc R . . . .
C12 C 0.1821(3) 0.3118(3) 0.0437(3) 0.0282(6) Uani 1 1 d . . . . .
H12 H 0.236209 0.284794 0.010941 0.034 Uiso 1 1 calc R . . . .
C13 C 0.0724(3) 0.2207(3) 0.0330(3) 0.0283(6) Uani 1 1 d . . . . .
H13 H 0.053255 0.132736 -0.006636 0.034 Uiso 1 1 calc R . . . .
C14 C -0.0091(3) 0.2600(3) 0.0809(3) 0.0293(6) Uani 1 1 d . . . . .
H14 H -0.083155 0.198486 0.072838 0.035 Uiso 1 1 calc R . . . .
C15 C 0.0200(3) 0.3914(3) 0.1410(3) 0.0272(6) Uani 1 1 d . . . . .
H15 H -0.034524 0.418159 0.173243 0.033 Uiso 1 1 calc R . . . .
C16 C -0.0913(3) 0.6596(3) 0.2669(3) 0.0264(6) Uani 1 1 d . . . . .
H16 H -0.139398 0.607849 0.175199 0.032 Uiso 1 1 calc R . . . .
C17 C -0.0759(3) 0.6146(3) 0.3623(3) 0.0261(6) Uani 1 1 d . . . . .
H17 H -0.111919 0.528003 0.344278 0.031 Uiso 1 1 calc R . . . .
C18 C 0.0046(3) 0.7251(3) 0.4913(3) 0.0264(6) Uani 1 1 d . . . . .
H18 H 0.030324 0.723543 0.572100 0.032 Uiso 1 1 calc R . . . .
C19 C 0.0376(3) 0.8365(3) 0.4734(3) 0.0245(6) Uani 1 1 d . . . . .
H19 H 0.089406 0.921903 0.541125 0.029 Uiso 1 1 calc R . . . .
C20 C -0.0206(3) 0.7978(3) 0.3354(3) 0.0245(5) Uani 1 1 d . . . . .
H20 H -0.013766 0.852675 0.296915 0.029 Uiso 1 1 calc R . . . .
F1 F 0.2167(2) 0.87652(18) 0.80777(19) 0.0390(4) Uani 1 1 d . . . . .
F2 F 0.2510(2) 1.06821(18) 0.79969(18) 0.0389(4) Uani 1 1 d . . . . .
F3 F 0.2612(2) 1.05532(18) 0.98167(16) 0.0390(4) Uani 1 1 d . . . . .
F4 F 0.05317(19) 0.9593(2) 0.78676(19) 0.0472(5) Uani 1 1 d . . . . .
B1 B 0.1950(3) 0.9899(3) 0.8445(3) 0.0225(6) Uani 1 1 d . . . . .
Cl1 Cl 0.43544(11) 0.61475(10) 0.82867(10) 0.0547(3) Uani 0.905(3) 1 d . . P A
-1
Cl2 Cl 0.35165(9) 0.71682(8) 1.01821(8) 0.0360(2) Uani 0.905(3) 1 d . . P A -1
C1A C 0.4305(5) 0.7520(4) 0.9301(4) 0.0411(9) Uani 0.905(3) 1 d . . P A -1
H1AA H 0.378227 0.786438 0.875361 0.049 Uiso 0.905(3) 1 calc R . P A -1
H1AB H 0.525791 0.818636 0.993138 0.049 Uiso 0.905(3) 1 calc R . P A -1
Cl1_1 Cl 0.374(2) 0.7375(19) 0.936(2) 0.103(5) Uiso 0.095(3) 1 d D U P A 2
Cl2_1 Cl 0.4906(19) 0.5491(17) 0.9739(18) 0.103(5) Uiso 0.095(3) 1 d D U P A 2
C1_1 C 0.449(8) 0.635(6) 0.881(6) 0.103(5) Uiso 0.095(3) 1 d D U P A 2
H1A_1 H 0.383151 0.572792 0.787509 0.124 Uiso 0.095(3) 1 calc R . P A 2
H1B_1 H 0.533795 0.686598 0.888875 0.124 Uiso 0.095(3) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Fe1 2.3330(5) . ?
Se1 O2 1.7671(18) . ?
Se1 C10 1.941(3) . ?
Ni1 S1 2.1528(8) . ?
Ni1 O2 1.8723(19) . ?
Ni1 N1 1.913(2) . ?
Ni1 N2 1.968(2) . ?
Fe1 S1 2.2491(9) . ?
Fe1 C1 1.745(3) . ?
Fe1 C16 2.098(3) . ?
Fe1 C17 2.084(3) . ?
Fe1 C18 2.106(3) . ?
Fe1 C19 2.120(3) . ?
Fe1 C20 2.122(3) . ?
S1 C2 1.838(3) . ?
O1 C1 1.150(3) . ?
N1 C3 1.495(3) . ?
N1 C4 1.497(3) . ?
N1 C6 1.507(3) . ?
N2 C5 1.486(3) . ?
N2 C8 1.487(4) . ?
N2 C9 1.480(3) . ?
C2 C3 1.512(4) . ?
C4 C5 1.532(4) . ?
C6 C7 1.522(4) . ?
C7 C8 1.519(4) . ?
C10 C11 1.389(4) . ?
C10 C15 1.384(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.388(4) . ?
C16 C17 1.410(4) . ?
C16 C20 1.421(4) . ?
C17 C18 1.429(4) . ?
C18 C19 1.404(4) . ?
C19 C20 1.418(4) . ?
F1 B1 1.394(4) . ?
F2 B1 1.391(4) . ?
F3 B1 1.382(3) . ?
F4 B1 1.374(3) . ?
Cl1 C1A 1.745(4) . ?
Cl2 C1A 1.764(4) . ?
Cl1_1 C1_1 1.768(10) . ?
Cl2_1 Cl2_1 1.52(3) 2_667 ?
Cl2_1 C1_1 1.762(10) . ?

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
O2 Se1 Fe1 109.49(6) . . ?
O2 Se1 C10 98.91(10) . . ?
C10 Se1 Fe1 106.82(8) . . ?
O2 Ni1 S1 92.74(6) . . ?
O2 Ni1 N1 175.12(9) . . ?
O2 Ni1 N2 93.98(9) . . ?
N1 Ni1 S1 90.95(7) . . ?
N1 Ni1 N2 82.48(9) . . ?
N2 Ni1 S1 172.88(7) . . ?
S1 Fe1 Se1 86.11(2) . . ?
C1 Fe1 Se1 95.04(9) . . ?
C1 Fe1 S1 93.41(9) . . ?
C1 Fe1 C16 123.77(12) . . ?
C1 Fe1 C17 92.46(12) . . ?
C1 Fe1 C18 96.02(12) . . ?
C1 Fe1 C19 130.50(11) . . ?
C1 Fe1 C20 158.29(12) . . ?
C16 Fe1 Se1 90.99(8) . . ?
C16 Fe1 S1 142.81(8) . . ?
C16 Fe1 C18 66.33(11) . . ?
C16 Fe1 C19 65.66(11) . . ?
C16 Fe1 C20 39.35(11) . . ?
C17 Fe1 Se1 119.82(8) . . ?
C17 Fe1 S1 152.76(8) . . ?
C17 Fe1 C16 39.42(11) . . ?
C17 Fe1 C18 39.87(11) . . ?
C17 Fe1 C19 65.73(11) . . ?
C17 Fe1 C20 66.04(11) . . ?
C18 Fe1 Se1 157.22(8) . . ?
C18 Fe1 S1 112.99(8) . . ?
C18 Fe1 C19 38.80(11) . . ?
C18 Fe1 C20 65.86(11) . . ?
C19 Fe1 Se1 134.46(8) . . ?
C19 Fe1 S1 90.58(8) . . ?
C19 Fe1 C20 39.06(11) . . ?
C20 Fe1 Se1 98.32(8) . . ?
C20 Fe1 S1 104.46(8) . . ?
Ni1 S1 Fe1 108.29(3) . . ?
C2 S1 Ni1 97.11(9) . . ?
C2 S1 Fe1 111.97(10) . . ?
Se1 O2 Ni1 120.99(10) . . ?
C3 N1 Ni1 112.40(16) . . ?
C3 N1 C4 110.3(2) . . ?
C3 N1 C6 110.3(2) . . ?
C4 N1 Ni1 108.43(16) . . ?
C4 N1 C6 109.9(2) . . ?
C6 N1 Ni1 105.33(16) . . ?
C5 N2 Ni1 106.88(16) . . ?
C5 N2 C8 109.8(2) . . ?
C8 N2 Ni1 105.37(17) . . ?
C9 N2 Ni1 116.43(17) . . ?
C9 N2 C5 109.2(2) . . ?
C9 N2 C8 109.0(2) . . ?
O1 C1 Fe1 176.7(2) . . ?
C3 C2 S1 105.09(18) . . ?
N1 C3 C2 109.4(2) . . ?
N1 C4 C5 109.4(2) . . ?
N2 C5 C4 110.9(2) . . ?
N1 C6 C7 111.8(2) . . ?
C8 C7 C6 115.9(2) . . ?
N2 C8 C7 111.9(2) . . ?
C11 C10 Se1 118.9(2) . . ?
C15 C10 Se1 120.3(2) . . ?
C15 C10 C11 120.5(3) . . ?
C12 C11 C10 119.4(3) . . ?
C13 C12 C11 120.1(3) . . ?
C14 C13 C12 120.3(3) . . ?
C13 C14 C15 119.9(3) . . ?
C10 C15 C14 119.7(3) . . ?
C17 C16 Fe1 69.76(15) . . ?
C17 C16 C20 108.1(2) . . ?
C20 C16 Fe1 71.25(15) . . ?
C16 C17 Fe1 70.82(15) . . ?
C16 C17 C18 108.2(2) . . ?
C18 C17 Fe1 70.90(15) . . ?
C17 C18 Fe1 69.23(15) . . ?
C19 C18 Fe1 71.12(15) . . ?
C19 C18 C17 107.3(2) . . ?
C18 C19 Fe1 70.08(15) . . ?
C18 C19 C20 109.1(2) . . ?
C20 C19 Fe1 70.56(15) . . ?
C16 C20 Fe1 69.41(15) . . ?
C19 C20 Fe1 70.38(15) . . ?
C19 C20 C16 107.3(2) . . ?
F2 B1 F1 108.8(2) . . ?
F3 B1 F1 109.4(2) . . ?
F3 B1 F2 109.8(2) . . ?
F4 B1 F1 109.9(2) . . ?
F4 B1 F2 108.8(2) . . ?
F4 B1 F3 110.2(2) . . ?
Cl1 C1A Cl2 112.2(2) . . ?
Cl2_1 Cl2_1 C1_1 168(3) 2_667 . ?
Cl2_1 C1_1 Cl1_1 111.6(14) . . ?

_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_040418_sheet
_database_code_depnum_ccdc_archive 'CCDC 1861580'
_audit_update_record             
;
2018-08-11 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 Fe N2 Ni O S Se, B F4'
_chemical_formula_sum            'C20 H27 B F4 Fe N2 Ni O S Se'
_chemical_formula_weight         623.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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                   8.7518(2)
_cell_length_b                   21.0078(6)
_cell_length_c                   13.1915(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.2270(10)
_cell_angle_gamma                90
_cell_volume                     2350.95(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9765
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.31
_cell_measurement_theta_min      4.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.972
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.4421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1479 before and 0.0869 after correction. The Ratio of minimum to maximum transmission is 0.5862. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31556
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.948
_diffrn_reflns_theta_min         4.209
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Micro-Source CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4749
_reflns_number_total             4985
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.336
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.00111(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4985
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.060
_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)+(0.0479P)²+13.9215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.48711(5) 0.44223(2) 0.84682(3) 0.01662(15) Uani 1 1 d . . . . .
Ni1 Ni 0.52906(8) 0.34322(3) 0.92619(5) 0.01524(18) Uani 1 1 d . . . . .
Fe1 Fe 0.74484(8) 0.43252(3) 0.81312(5) 0.01823(18) Uani 1 1 d . . . . .
S1 S 0.68658(12) 0.32825(5) 0.82813(8) 0.0196(2) Uani 1 1 d . . . . .
O1 O 0.8855(4) 0.45147(17) 1.0354(3) 0.0307(7) Uani 1 1 d . . . . .
N1 N 0.6177(4) 0.27323(16) 1.0158(3) 0.0181(7) Uani 1 1 d . . . . .
N2 N 0.3815(4) 0.34520(17) 1.0165(3) 0.0199(7) Uani 1 1 d . . . . .
C1 C 0.8298(5) 0.4441(2) 0.9473(4) 0.0228(9) Uani 1 1 d . . . . .
C2 C 0.8407(5) 0.5133(2) 0.7572(4) 0.0234(9) Uani 1 1 d . . . . .
H2 H 0.866081 0.552405 0.793735 0.028 Uiso 1 1 calc R . . . .
C3 C 0.9435(5) 0.4599(2) 0.7620(4) 0.0252(9) Uani 1 1 d . . . . .
H3 H 1.049275 0.457213 0.802402 0.030 Uiso 1 1 calc R . . . .
C4 C 0.8605(6) 0.4122(2) 0.6964(4) 0.0311(11) Uani 1 1 d . . . . .
H4 H 0.901678 0.371805 0.684301 0.037 Uiso 1 1 calc R . . . .
C5 C 0.7046(6) 0.4340(2) 0.6509(4) 0.0292(10) Uani 1 1 d . . . . .
H5 H 0.622959 0.411030 0.604655 0.035 Uiso 1 1 calc R . . . .
C6 C 0.6951(6) 0.4977(2) 0.6888(4) 0.0289(10) Uani 1 1 d . . . . .
H6 H 0.605503 0.524662 0.670695 0.035 Uiso 1 1 calc R . . . .
C7 C 0.3408(5) 0.4306(2) 0.7130(3) 0.0203(8) Uani 1 1 d . . . . .
C8 C 0.2951(6) 0.4850(2) 0.6519(4) 0.0293(10) Uani 1 1 d . . . . .
H8 H 0.333634 0.525614 0.677950 0.035 Uiso 1 1 calc R . . . .
C9 C 0.1941(6) 0.4797(3) 0.5538(4) 0.0340(11) Uani 1 1 d . . . . .
H9 H 0.162503 0.516683 0.512504 0.041 Uiso 1 1 calc R . . . .
C10 C 0.1396(6) 0.4210(3) 0.5160(4) 0.0379(13) Uani 1 1 d . . . . .
H10 H 0.074055 0.417157 0.447249 0.045 Uiso 1 1 calc R . . . .
C11 C 0.1796(6) 0.3671(3) 0.5776(4) 0.0338(11) Uani 1 1 d . . . . .
H11 H 0.137722 0.326870 0.551968 0.041 Uiso 1 1 calc R . . . .
C12 C 0.2809(5) 0.3717(2) 0.6772(4) 0.0249(9) Uani 1 1 d . . . . .
H12 H 0.308314 0.334924 0.719586 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8304(6) 0.2797(2) 0.9229(4) 0.0296(10) Uani 1 1 d . . . . .
H13A H 0.898478 0.255147 0.887221 0.036 Uiso 1 1 calc R . . . .
H13B H 0.897820 0.306961 0.977116 0.036 Uiso 1 1 calc R . . . .
C14 C 0.7300(6) 0.2353(2) 0.9710(4) 0.0252(9) Uani 1 1 d . . . . .
H14A H 0.670439 0.205948 0.916852 0.030 Uiso 1 1 calc R . . . .
H14B H 0.798880 0.209551 1.026795 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7048(5) 0.3032(2) 1.1168(3) 0.0218(9) Uani 1 1 d . . . . .
H15A H 0.773587 0.337531 1.101651 0.026 Uiso 1 1 calc R . . . .
H15B H 0.773144 0.270853 1.160256 0.026 Uiso 1 1 calc R . . . .
C16 C 0.5940(6) 0.3309(2) 1.1782(3) 0.0238(9) Uani 1 1 d . . . . .
H16A H 0.543918 0.295265 1.207064 0.029 Uiso 1 1 calc R . . . .
H16B H 0.657575 0.355297 1.238124 0.029 Uiso 1 1 calc R . . . .
C17 C 0.4649(6) 0.3741(2) 1.1170(4) 0.0250(9) Uani 1 1 d . . . . .
H17A H 0.388359 0.382885 1.159454 0.030 Uiso 1 1 calc R . . . .
H17B H 0.511728 0.415128 1.103400 0.030 Uiso 1 1 calc R . . . .
C18 C 0.4829(5) 0.2337(2) 1.0329(3) 0.0192(8) Uani 1 1 d . . . . .
H18A H 0.513936 0.212212 1.101646 0.023 Uiso 1 1 calc R . . . .
H18B H 0.454868 0.200669 0.977914 0.023 Uiso 1 1 calc R . . . .
C19 C 0.3405(5) 0.2772(2) 1.0290(3) 0.0198(8) Uani 1 1 d . . . . .
H19A H 0.252501 0.264525 0.969645 0.024 Uiso 1 1 calc R . . . .
H19B H 0.304989 0.272220 1.094231 0.024 Uiso 1 1 calc R . . . .
C20 C 0.2328(5) 0.3810(2) 0.9742(4) 0.0281(10) Uani 1 1 d . . . . .
H20A H 0.256652 0.426324 0.969959 0.042 Uiso 1 1 calc GR . . . .
H20B H 0.161822 0.375190 1.020581 0.042 Uiso 1 1 calc GR . . . .
H20C H 0.181840 0.364970 0.904318 0.042 Uiso 1 1 calc GR . . . .
F1 F 0.2809(5) 0.2944(3) 0.2934(3) 0.097(2) Uani 1 1 d . . . . .
F2 F 0.0829(4) 0.3238(2) 0.1613(3) 0.0546(10) Uani 1 1 d . . . . .
F3 F 0.0429(7) 0.3258(2) 0.3215(4) 0.0895(19) Uani 1 1 d . . . . .
F4 F 0.0631(5) 0.23344(18) 0.2477(4) 0.0721(14) Uani 1 1 d . . . . .
B1 B 0.1198(6) 0.2946(3) 0.2576(4) 0.0297(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Ni1 2.3171(8) . ?
Se1 Fe1 2.4124(8) . ?
Se1 C7 1.925(4) . ?
Ni1 S1 2.1329(12) . ?
Ni1 N1 1.926(3) . ?
Ni1 N2 1.962(4) . ?
Fe1 S1 2.2688(12) . ?
Fe1 C1 1.760(5) . ?
Fe1 C2 2.105(4) . ?
Fe1 C3 2.094(4) . ?
Fe1 C4 2.084(5) . ?
Fe1 C5 2.081(5) . ?
Fe1 C6 2.097(5) . ?
S1 C13 1.848(5) . ?
O1 C1 1.155(6) . ?
N1 C14 1.495(5) . ?
N1 C15 1.502(5) . ?
N1 C18 1.504(5) . ?
N2 C17 1.478(6) . ?
N2 C19 1.491(5) . ?
N2 C20 1.488(6) . ?
C2 C3 1.430(6) . ?
C2 C6 1.407(7) . ?
C3 C4 1.405(7) . ?
C4 C5 1.424(8) . ?
C5 C6 1.437(7) . ?
C7 C8 1.398(6) . ?
C7 C12 1.381(7) . ?
C8 C9 1.381(7) . ?
C9 C10 1.372(9) . ?
C10 C11 1.387(8) . ?
C11 C12 1.395(7) . ?
C13 C14 1.522(7) . ?
C15 C16 1.524(6) . ?
C16 C17 1.517(7) . ?
C18 C19 1.536(6) . ?
F1 B1 1.373(7) . ?
F2 B1 1.376(6) . ?
F3 B1 1.367(7) . ?
F4 B1 1.372(7) . ?

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
Ni1 Se1 Fe1 87.47(3) . . ?
C7 Se1 Ni1 107.26(13) . . ?
C7 Se1 Fe1 105.19(13) . . ?
S1 Ni1 Se1 84.98(4) . . ?
N1 Ni1 Se1 163.29(11) . . ?
N1 Ni1 S1 92.12(11) . . ?
N1 Ni1 N2 82.48(15) . . ?
N2 Ni1 Se1 101.57(11) . . ?
N2 Ni1 S1 172.73(11) . . ?
S1 Fe1 Se1 79.94(3) . . ?
C1 Fe1 Se1 89.21(14) . . ?
C1 Fe1 S1 95.43(15) . . ?
C1 Fe1 C2 97.70(19) . . ?
C1 Fe1 C3 96.1(2) . . ?
C1 Fe1 C4 127.5(2) . . ?
C1 Fe1 C5 162.6(2) . . ?
C1 Fe1 C6 130.6(2) . . ?
C2 Fe1 Se1 117.86(13) . . ?
C2 Fe1 S1 157.89(14) . . ?
C3 Fe1 Se1 157.51(14) . . ?
C3 Fe1 S1 121.05(14) . . ?
C3 Fe1 C2 39.81(18) . . ?
C3 Fe1 C6 66.29(18) . . ?
C4 Fe1 Se1 143.06(16) . . ?
C4 Fe1 S1 91.53(14) . . ?
C4 Fe1 C2 66.37(19) . . ?
C4 Fe1 C3 39.3(2) . . ?
C4 Fe1 C6 66.5(2) . . ?
C5 Fe1 Se1 104.98(15) . . ?
C5 Fe1 S1 96.86(14) . . ?
C5 Fe1 C2 66.99(18) . . ?
C5 Fe1 C3 66.97(19) . . ?
C5 Fe1 C4 40.0(2) . . ?
C5 Fe1 C6 40.2(2) . . ?
C6 Fe1 Se1 93.74(13) . . ?
C6 Fe1 S1 133.65(15) . . ?
C6 Fe1 C2 39.12(18) . . ?
Ni1 S1 Fe1 95.92(5) . . ?
C13 S1 Ni1 96.05(15) . . ?
C13 S1 Fe1 117.49(18) . . ?
C14 N1 Ni1 111.6(3) . . ?
C14 N1 C15 109.5(3) . . ?
C14 N1 C18 112.4(3) . . ?
C15 N1 Ni1 105.3(3) . . ?
C15 N1 C18 110.2(3) . . ?
C18 N1 Ni1 107.5(2) . . ?
C17 N2 Ni1 107.5(3) . . ?
C17 N2 C19 112.0(3) . . ?
C17 N2 C20 108.8(4) . . ?
C19 N2 Ni1 105.0(2) . . ?
C20 N2 Ni1 115.4(3) . . ?
C20 N2 C19 108.2(3) . . ?
O1 C1 Fe1 179.7(4) . . ?
C3 C2 Fe1 69.7(2) . . ?
C6 C2 Fe1 70.1(3) . . ?
C6 C2 C3 107.8(4) . . ?
C2 C3 Fe1 70.5(2) . . ?
C4 C3 Fe1 70.0(3) . . ?
C4 C3 C2 108.0(4) . . ?
C3 C4 Fe1 70.7(3) . . ?
C3 C4 C5 109.0(4) . . ?
C5 C4 Fe1 69.9(3) . . ?
C4 C5 Fe1 70.1(3) . . ?
C4 C5 C6 106.5(4) . . ?
C6 C5 Fe1 70.5(3) . . ?
C2 C6 Fe1 70.7(3) . . ?
C2 C6 C5 108.7(4) . . ?
C5 C6 Fe1 69.3(3) . . ?
C8 C7 Se1 117.2(4) . . ?
C12 C7 Se1 122.6(3) . . ?
C12 C7 C8 120.3(4) . . ?
C9 C8 C7 120.1(5) . . ?
C10 C9 C8 119.9(5) . . ?
C9 C10 C11 120.4(5) . . ?
C10 C11 C12 120.3(5) . . ?
C7 C12 C11 119.0(4) . . ?
C14 C13 S1 104.7(3) . . ?
N1 C14 C13 110.0(4) . . ?
N1 C15 C16 112.4(4) . . ?
C17 C16 C15 115.7(4) . . ?
N2 C17 C16 111.8(4) . . ?
N1 C18 C19 109.0(3) . . ?
N2 C19 C18 111.0(3) . . ?
F1 B1 F2 107.9(4) . . ?
F3 B1 F1 114.1(5) . . ?
F3 B1 F2 108.5(5) . . ?
F3 B1 F4 106.6(4) . . ?
F4 B1 F1 110.3(6) . . ?
F4 B1 F2 109.4(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_040418_needle
_database_code_depnum_ccdc_archive 'CCDC 1861579'
_audit_update_record             
;
2018-08-11 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 Fe N2 Ni O S Se, B F4'
_chemical_formula_sum            'C20 H27 B F4 Fe N2 Ni O S Se'
_chemical_formula_weight         623.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.3090(5)
_cell_length_b                   11.4239(4)
_cell_length_c                   24.8441(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4628.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9171
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.39
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.463
_shelx_estimated_absorpt_T_min   0.263
_exptl_absorpt_coefficient_mu    9.113
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1646 before and 0.0866 after correction. The Ratio of minimum to maximum transmission is 0.3085. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            60448
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.517
_diffrn_reflns_theta_min         4.474
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Micro-Source CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4430
_reflns_number_total             4563
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       0.00106(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.143
_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)+(0.1000P)²+37.6341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.1976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C14(H14A,H14B), C15(H15A,H15B), C13(H13A,
 H13B), C17(H17A,H17B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C12(H12), C8(H8), C10(H10), C5(H5), C11(H11), C6(H6), C9(H9),
 C2(H2)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.51802(4) 0.39758(5) 0.42777(2) 0.0203(2) Uani 1 1 d . . . . .
Ni1 Ni 0.49926(6) 0.25087(9) 0.36492(4) 0.0182(3) Uani 1 1 d . . . . .
Fe1 Fe 0.60522(6) 0.26342(10) 0.47569(4) 0.0261(3) Uani 1 1 d . . . . .
S1 S 0.61702(9) 0.19212(14) 0.39103(6) 0.0232(4) Uani 1 1 d . . . . .
F4 F 0.5699(2) 0.3124(4) 0.2545(2) 0.0424(10) Uani 1 1 d . . . . .
F3 F 0.6673(3) 0.1729(4) 0.2407(2) 0.0478(11) Uani 1 1 d . . . . .
O1 O 0.4636(3) 0.1260(5) 0.5072(2) 0.0398(12) Uani 1 1 d . . . . .
N1 N 0.4741(3) 0.1008(4) 0.3333(2) 0.0232(11) Uani 1 1 d . . . . .
N2 N 0.3939(3) 0.2941(5) 0.3342(2) 0.0217(10) Uani 1 1 d . . . . .
F2 F 0.6946(3) 0.3637(5) 0.2284(3) 0.081(2) Uani 1 1 d . . . . .
C18 C 0.4381(4) 0.1202(5) 0.2794(2) 0.0247(13) Uani 1 1 d . . . . .
H18A H 0.400114 0.055532 0.270450 0.030 Uiso 1 1 calc R . . . .
H18B H 0.482065 0.122063 0.251919 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7185(4) 0.3490(7) 0.4802(3) 0.0362(17) Uani 1 1 d . . . . .
H4 H 0.744078 0.389016 0.451137 0.043 Uiso 1 1 calc R . . . .
C7 C 0.5887(4) 0.5132(6) 0.3952(2) 0.0238(12) Uani 1 1 d . . . . .
C1 C 0.5193(4) 0.1792(6) 0.4941(3) 0.0296(14) Uani 1 1 d . . . . .
C19 C 0.3912(4) 0.2382(6) 0.2795(3) 0.0266(14) Uani 1 1 d . . . . .
H19A H 0.416103 0.291678 0.252789 0.032 Uiso 1 1 calc R . . . .
H19B H 0.333448 0.224590 0.269032 0.032 Uiso 1 1 calc R . . . .
C3 C 0.7287(4) 0.2282(8) 0.4932(3) 0.0387(17) Uani 1 1 d . . . . .
H3 H 0.762532 0.173922 0.474528 0.046 Uiso 1 1 calc R . . . .
C14 C 0.5493(4) 0.0235(6) 0.3303(3) 0.0317(14) Uani 1 1 d . . . . .
H14A H 0.583778 0.047078 0.299331 0.038 Uiso 1 1 calc R . . . .
H14B H 0.532584 -0.059048 0.325050 0.038 Uiso 1 1 calc R . . . .
C15 C 0.4119(4) 0.0483(6) 0.3706(3) 0.0311(14) Uani 1 1 d . . . . .
H15A H 0.431773 0.055027 0.408087 0.037 Uiso 1 1 calc R . . . .
H15B H 0.405630 -0.035914 0.362172 0.037 Uiso 1 1 calc R . . . .
C12 C 0.6418(4) 0.4876(6) 0.3526(3) 0.0296(14) Uani 1 1 d . . . . .
H12 H 0.645700 0.410100 0.338960 0.036 Uiso 1 1 calc R . . . .
C20 C 0.3775(4) 0.4218(6) 0.3284(3) 0.0278(13) Uani 1 1 d . . . . .
H20A H 0.371122 0.457054 0.364086 0.042 Uiso 1 1 calc GR . . . .
H20B H 0.327096 0.433247 0.307569 0.042 Uiso 1 1 calc GR . . . .
H20C H 0.423507 0.458939 0.309626 0.042 Uiso 1 1 calc GR . . . .
C13 C 0.5978(4) 0.0354(6) 0.3823(3) 0.0315(14) Uani 1 1 d . . . . .
H13A H 0.650179 -0.008097 0.379735 0.038 Uiso 1 1 calc R . . . .
H13B H 0.565986 0.004128 0.413004 0.038 Uiso 1 1 calc R . . . .
C8 C 0.5815(4) 0.6271(6) 0.4142(3) 0.0322(15) Uani 1 1 d . . . . .
H8 H 0.545299 0.644154 0.443047 0.039 Uiso 1 1 calc R . . . .
C17 C 0.3300(4) 0.2399(6) 0.3696(3) 0.0264(13) Uani 1 1 d . . . . .
H17A H 0.275523 0.271249 0.359470 0.032 Uiso 1 1 calc R . . . .
H17B H 0.340676 0.262702 0.407437 0.032 Uiso 1 1 calc R . . . .
F1 F 0.6113(6) 0.2679(7) 0.1721(2) 0.110(3) Uani 1 1 d . . . . .
C16 C 0.3280(4) 0.1087(6) 0.3659(3) 0.0323(16) Uani 1 1 d . . . . .
H16A H 0.303069 0.086674 0.330965 0.039 Uiso 1 1 calc R . . . .
H16B H 0.291857 0.078360 0.394704 0.039 Uiso 1 1 calc R . . . .
C10 C 0.6808(5) 0.6916(7) 0.3495(3) 0.0369(17) Uani 1 1 d . . . . .
H10 H 0.712516 0.752427 0.333826 0.044 Uiso 1 1 calc R . . . .
C5 C 0.6637(5) 0.3991(8) 0.5180(3) 0.0393(18) Uani 1 1 d . . . . .
H5 H 0.646446 0.478491 0.518685 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6885(4) 0.5761(7) 0.3305(3) 0.0310(15) Uani 1 1 d . . . . .
H11 H 0.725942 0.559003 0.302311 0.037 Uiso 1 1 calc R . . . .
B1 B 0.6366(5) 0.2776(6) 0.2237(3) 0.0262(15) Uani 1 1 d . . . . .
C6 C 0.6391(5) 0.3116(11) 0.5541(3) 0.059(3) Uani 1 1 d . . . . .
H6 H 0.602427 0.321093 0.583523 0.070 Uiso 1 1 calc R . . . .
C9 C 0.6277(5) 0.7164(7) 0.3907(3) 0.0406(18) Uani 1 1 d . . . . .
H9 H 0.622371 0.794500 0.403358 0.049 Uiso 1 1 calc R . . . .
C2 C 0.6800(5) 0.2036(10) 0.5384(3) 0.058(3) Uani 1 1 d . . . . .
H2 H 0.674692 0.129716 0.555647 0.069 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Ni1 2.3110(11) . ?
Se1 Fe1 2.4059(12) . ?
Se1 C7 1.930(6) . ?
Ni1 S1 2.1353(17) . ?
Ni1 N1 1.929(5) . ?
Ni1 N2 1.943(5) . ?
Fe1 S1 2.2635(18) . ?
Fe1 C4 2.093(7) . ?
Fe1 C1 1.760(7) . ?
Fe1 C3 2.100(7) . ?
Fe1 C5 2.101(7) . ?
Fe1 C6 2.099(8) . ?
Fe1 C2 2.094(7) . ?
S1 C13 1.831(7) . ?
F4 B1 1.388(8) . ?
F3 B1 1.364(8) . ?
O1 C1 1.140(8) . ?
N1 C18 1.479(8) . ?
N1 C14 1.513(8) . ?
N1 C15 1.499(8) . ?
N2 C19 1.502(8) . ?
N2 C20 1.490(8) . ?
N2 C17 1.498(8) . ?
F2 B1 1.370(10) . ?
C18 C19 1.549(9) . ?
C4 C3 1.428(12) . ?
C4 C5 1.418(11) . ?
C7 C12 1.399(9) . ?
C7 C8 1.389(10) . ?
C3 C2 1.405(11) . ?
C14 C13 1.520(10) . ?
C15 C16 1.537(10) . ?
C12 C11 1.379(9) . ?
C8 C9 1.396(10) . ?
C17 C16 1.502(9) . ?
F1 B1 1.350(10) . ?
C10 C11 1.407(11) . ?
C10 C9 1.370(12) . ?
C5 C6 1.402(13) . ?
C6 C2 1.457(16) . ?

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
Ni1 Se1 Fe1 87.17(4) . . ?
C7 Se1 Ni1 106.96(19) . . ?
C7 Se1 Fe1 106.89(19) . . ?
S1 Ni1 Se1 84.47(6) . . ?
N1 Ni1 Se1 161.34(16) . . ?
N1 Ni1 S1 92.04(17) . . ?
N1 Ni1 N2 83.0(2) . . ?
N2 Ni1 Se1 101.41(16) . . ?
N2 Ni1 S1 173.80(16) . . ?
S1 Fe1 Se1 79.62(5) . . ?
C4 Fe1 Se1 104.5(2) . . ?
C4 Fe1 S1 98.2(2) . . ?
C4 Fe1 C3 39.8(3) . . ?
C4 Fe1 C5 39.5(3) . . ?
C1 Fe1 Se1 90.3(2) . . ?
C1 Fe1 S1 96.4(2) . . ?
C1 Fe1 C4 160.8(3) . . ?
C1 Fe1 C3 127.3(3) . . ?
C1 Fe1 C5 129.4(3) . . ?
C1 Fe1 C6 96.4(3) . . ?
C1 Fe1 C2 95.3(3) . . ?
C3 Fe1 Se1 142.3(2) . . ?
C3 Fe1 S1 92.4(2) . . ?
C5 Fe1 Se1 92.6(2) . . ?
C5 Fe1 S1 133.7(2) . . ?
C5 Fe1 C3 66.6(3) . . ?
C6 Fe1 Se1 116.6(3) . . ?
C6 Fe1 S1 159.2(3) . . ?
C6 Fe1 C4 66.2(3) . . ?
C6 Fe1 C3 66.8(3) . . ?
C6 Fe1 C5 39.0(4) . . ?
C6 Fe1 C2 40.7(4) . . ?
C2 Fe1 Se1 157.0(4) . . ?
C2 Fe1 S1 121.6(3) . . ?
C2 Fe1 C4 66.4(3) . . ?
C2 Fe1 C3 39.1(3) . . ?
C2 Fe1 C5 66.7(4) . . ?
Ni1 S1 Fe1 95.32(7) . . ?
C13 S1 Ni1 96.7(2) . . ?
C13 S1 Fe1 116.6(2) . . ?
C18 N1 Ni1 108.7(4) . . ?
C18 N1 C14 111.4(5) . . ?
C18 N1 C15 110.5(5) . . ?
C14 N1 Ni1 111.5(4) . . ?
C15 N1 Ni1 104.3(4) . . ?
C15 N1 C14 110.2(5) . . ?
C19 N2 Ni1 105.8(4) . . ?
C20 N2 Ni1 116.5(4) . . ?
C20 N2 C19 108.8(5) . . ?
C20 N2 C17 109.7(5) . . ?
C17 N2 Ni1 106.3(4) . . ?
C17 N2 C19 109.6(5) . . ?
N1 C18 C19 108.9(5) . . ?
C3 C4 Fe1 70.3(4) . . ?
C5 C4 Fe1 70.5(4) . . ?
C5 C4 C3 108.3(7) . . ?
C12 C7 Se1 123.0(5) . . ?
C8 C7 Se1 116.7(5) . . ?
C8 C7 C12 120.3(6) . . ?
O1 C1 Fe1 178.2(6) . . ?
N2 C19 C18 110.9(5) . . ?
C4 C3 Fe1 69.9(4) . . ?
C2 C3 Fe1 70.2(4) . . ?
C2 C3 C4 108.0(8) . . ?
N1 C14 C13 109.1(5) . . ?
N1 C15 C16 112.1(6) . . ?
C11 C12 C7 119.3(7) . . ?
C14 C13 S1 106.1(5) . . ?
C9 C8 C7 119.9(7) . . ?
N2 C17 C16 113.0(5) . . ?
C17 C16 C15 115.1(5) . . ?
C9 C10 C11 120.1(6) . . ?
C4 C5 Fe1 70.0(4) . . ?
C6 C5 Fe1 70.4(5) . . ?
C6 C5 C4 108.5(8) . . ?
C12 C11 C10 120.3(7) . . ?
F3 B1 F4 111.7(6) . . ?
F3 B1 F2 110.4(6) . . ?
F2 B1 F4 106.9(6) . . ?
F1 B1 F4 107.9(7) . . ?
F1 B1 F3 109.5(7) . . ?
F1 B1 F2 110.5(7) . . ?
C5 C6 Fe1 70.6(4) . . ?
C5 C6 C2 107.5(7) . . ?
C2 C6 Fe1 69.5(5) . . ?
C10 C9 C8 120.1(7) . . ?
C3 C2 Fe1 70.7(4) . . ?
C3 C2 C6 107.7(8) . . ?
C6 C2 Fe1 69.9(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_md_a
_database_code_depnum_ccdc_archive 'CCDC 1861578'
_audit_update_record             
;
2018-08-11 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_audit_creation_date             2017-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 Fe N2 Ni O S2, 0.78(B F4), 0.22(Cl)'
_chemical_formula_sum            'C20 H27 B0.78 Cl0.22 F3.13 Fe N2 Ni O S2'
_chemical_formula_weight         565.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.2504(6)
_cell_length_b                   11.3127(4)
_cell_length_c                   24.8851(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4574.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.413
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5117
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1201 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.6790. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             2326
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            54741
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.354
_diffrn_reflns_theta_min         3.552
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD APEX2 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4155
_reflns_number_total             4521
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.174
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.00013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.180
_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)+(0.0512P)²+26.4449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{B1, Cl1}
3. Uiso/Uaniso restraints and constraints
Uanis(B1) = Uanis(Cl1)
4. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(B1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.50487(5) 0.75119(7) 0.63374(3) 0.0214(2) Uani 1 1 d . . . . .
Fe1 Fe 0.60628(5) 0.73116(8) 0.52530(3) 0.0272(2) Uani 1 1 d . . . . .
S1 S 0.62377(7) 0.80987(11) 0.60858(5) 0.0264(3) Uani 1 1 d . . . . .
S2 S 0.52402(7) 0.60779(11) 0.57541(5) 0.0241(3) Uani 1 1 d . . . . .
O1 O 0.4653(3) 0.8718(4) 0.49300(16) 0.0424(10) Uani 1 1 d . . . . .
N1 N 0.4792(3) 0.9032(4) 0.66485(16) 0.0256(9) Uani 1 1 d . . . . .
N2 N 0.3984(2) 0.7076(4) 0.66375(16) 0.0248(9) Uani 1 1 d . . . . .
C1 C 0.5207(4) 0.8164(5) 0.5071(2) 0.0316(12) Uani 1 1 d . . . . .
C2 C 0.6044(4) 0.9680(5) 0.6169(2) 0.0358(13) Uani 1 1 d . . . . .
H2A H 0.656876 1.011815 0.620114 0.043 Uiso 1 1 calc R . . . .
H2B H 0.573461 0.999455 0.585752 0.043 Uiso 1 1 calc R . . . .
C3 C 0.5542(4) 0.9802(5) 0.6680(2) 0.0323(12) Uani 1 1 d . . . . .
H3A H 0.588027 0.956887 0.699284 0.039 Uiso 1 1 calc R . . . .
H3B H 0.537407 1.063685 0.672771 0.039 Uiso 1 1 calc R . . . .
C4 C 0.4169(4) 0.9555(5) 0.6274(2) 0.0334(12) Uani 1 1 d . . . . .
H4A H 0.437409 0.949152 0.590100 0.040 Uiso 1 1 calc R . . . .
H4B H 0.410177 1.040485 0.635863 0.040 Uiso 1 1 calc R . . . .
C5 C 0.3331(4) 0.8945(5) 0.6313(2) 0.0375(13) Uani 1 1 d . . . . .
H5A H 0.307377 0.916721 0.665955 0.045 Uiso 1 1 calc R . . . .
H5B H 0.297444 0.925241 0.602243 0.045 Uiso 1 1 calc R . . . .
C6 C 0.3350(3) 0.7618(5) 0.6275(2) 0.0329(12) Uani 1 1 d . . . . .
H6A H 0.280131 0.730166 0.637098 0.039 Uiso 1 1 calc R . . . .
H6B H 0.346806 0.738687 0.589942 0.039 Uiso 1 1 calc R . . . .
C7 C 0.4420(3) 0.8821(5) 0.71893(19) 0.0283(11) Uani 1 1 d . . . . .
H7A H 0.403861 0.947405 0.727953 0.034 Uiso 1 1 calc R . . . .
H7B H 0.485802 0.879717 0.746547 0.034 Uiso 1 1 calc R . . . .
C8 C 0.3950(3) 0.7643(5) 0.7185(2) 0.0292(11) Uani 1 1 d . . . . .
H8A H 0.419461 0.710135 0.745411 0.035 Uiso 1 1 calc R . . . .
H8B H 0.336920 0.778286 0.728648 0.035 Uiso 1 1 calc R . . . .
C9 C 0.3822(3) 0.5788(5) 0.6696(2) 0.0324(12) Uani 1 1 d . . . . .
H9A H 0.375527 0.543300 0.633911 0.049 Uiso 1 1 calc GR . . . .
H9B H 0.331834 0.567019 0.690526 0.049 Uiso 1 1 calc GR . . . .
H9C H 0.428603 0.541328 0.688074 0.049 Uiso 1 1 calc GR . . . .
C10 C 0.5866(3) 0.4953(5) 0.60513(19) 0.0259(10) Uani 1 1 d . . . . .
C11 C 0.5800(4) 0.3826(5) 0.5841(2) 0.0358(13) Uani 1 1 d . . . . .
H11 H 0.545449 0.368145 0.554006 0.043 Uiso 1 1 calc R . . . .
C12 C 0.6240(4) 0.2907(5) 0.6072(3) 0.0426(15) Uani 1 1 d . . . . .
H12 H 0.618835 0.213059 0.593032 0.051 Uiso 1 1 calc R . . . .
C13 C 0.6748(4) 0.3104(5) 0.6500(2) 0.0385(14) Uani 1 1 d . . . . .
H13 H 0.704713 0.246767 0.665541 0.046 Uiso 1 1 calc R . . . .
C14 C 0.6826(3) 0.4234(5) 0.6708(2) 0.0342(12) Uani 1 1 d . . . . .
H14 H 0.718772 0.437403 0.700091 0.041 Uiso 1 1 calc R . . . .
C15 C 0.6380(3) 0.5163(5) 0.6491(2) 0.0305(11) Uani 1 1 d . . . . .
H15 H 0.642376 0.593361 0.663902 0.037 Uiso 1 1 calc R . . . .
C16 C 0.6589(4) 0.5910(6) 0.4816(2) 0.0433(15) Uani 1 1 d . . . . .
H16 H 0.638786 0.512148 0.481048 0.052 Uiso 1 1 calc R . . . .
C17 C 0.7173(4) 0.6375(6) 0.5186(2) 0.0398(14) Uani 1 1 d . . . . .
H17 H 0.742806 0.595217 0.547068 0.048 Uiso 1 1 calc R . . . .
C18 C 0.7307(4) 0.7582(7) 0.5056(2) 0.0455(16) Uani 1 1 d . . . . .
H18 H 0.767282 0.810256 0.523690 0.055 Uiso 1 1 calc R . . . .
C19 C 0.6802(4) 0.7879(8) 0.4611(3) 0.056(2) Uani 1 1 d . . . . .
H19 H 0.676133 0.863137 0.444366 0.067 Uiso 1 1 calc R . . . .
C20 C 0.6362(4) 0.6820(8) 0.4461(2) 0.0503(18) Uani 1 1 d . . . . .
H20 H 0.598401 0.675003 0.417144 0.060 Uiso 1 1 calc R . . . .
F1 F 0.6701(3) 0.8307(3) 0.76017(18) 0.0423(12) Uani 0.783(5) 1 d . . P A 1
F2 F 0.6984(3) 0.6388(4) 0.7723(3) 0.082(2) Uani 0.783(5) 1 d . . P A 1
F3 F 0.5722(2) 0.6888(3) 0.74906(18) 0.0368(10) Uani 0.783(5) 1 d . . P A 1
F4 F 0.6209(6) 0.7338(6) 0.8302(2) 0.114(4) Uani 0.783(5) 1 d . . P A 1
B1 B 0.63763(17) 0.7312(2) 0.77932(11) 0.0180(8) Uani 0.783(5) 1 d . . P A 1
Cl1 Cl 0.63763(17) 0.7312(2) 0.77932(11) 0.0180(8) Uani 0.217(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1368(15) . ?
Ni1 S2 2.1990(14) . ?
Ni1 N1 1.931(4) . ?
Ni1 N2 1.947(4) . ?
Fe1 S1 2.2736(15) . ?
Fe1 S2 2.3000(15) . ?
Fe1 C1 1.752(6) . ?
Fe1 C16 2.104(6) . ?
Fe1 C17 2.098(6) . ?
Fe1 C18 2.102(6) . ?
Fe1 C19 2.099(6) . ?
Fe1 C20 2.105(6) . ?
S1 C2 1.828(6) . ?
S2 C10 1.789(5) . ?
O1 C1 1.152(7) . ?
N1 C3 1.500(7) . ?
N1 C4 1.498(6) . ?
N1 C7 1.495(6) . ?
N2 C6 1.500(6) . ?
N2 C8 1.507(6) . ?
N2 C9 1.488(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.516(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.529(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.505(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.536(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.382(8) . ?
C10 C15 1.396(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.422(9) . ?
C16 C20 1.407(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.420(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.419(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.444(12) . ?
C20 H20 0.9500 . ?
F1 B1 1.331(5) . ?
F2 B1 1.449(6) . ?
F3 B1 1.389(5) . ?
F4 B1 1.294(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Ni1 S2 84.71(5) . . ?
N1 Ni1 S1 92.08(14) . . ?
N1 Ni1 S2 162.17(13) . . ?
N1 Ni1 N2 83.09(18) . . ?
N2 Ni1 S1 173.78(13) . . ?
N2 Ni1 S2 101.07(13) . . ?
S1 Fe1 S2 79.40(5) . . ?
C1 Fe1 S1 96.86(18) . . ?
C1 Fe1 S2 90.76(19) . . ?
C1 Fe1 C16 127.2(2) . . ?
C1 Fe1 C17 160.0(2) . . ?
C1 Fe1 C18 128.5(3) . . ?
C1 Fe1 C19 95.1(3) . . ?
C1 Fe1 C20 95.0(2) . . ?
C16 Fe1 S1 135.65(18) . . ?
C16 Fe1 S2 93.38(19) . . ?
C16 Fe1 C20 39.1(3) . . ?
C17 Fe1 S1 99.35(17) . . ?
C17 Fe1 S2 103.66(18) . . ?
C17 Fe1 C16 39.6(2) . . ?
C17 Fe1 C18 39.5(3) . . ?
C17 Fe1 C19 66.6(2) . . ?
C17 Fe1 C20 66.0(2) . . ?
C18 Fe1 S1 92.01(19) . . ?
C18 Fe1 S2 140.66(19) . . ?
C18 Fe1 C16 66.3(3) . . ?
C18 Fe1 C20 66.3(3) . . ?
C19 Fe1 S1 120.2(3) . . ?
C19 Fe1 S2 158.6(3) . . ?
C19 Fe1 C16 66.7(3) . . ?
C19 Fe1 C18 39.5(2) . . ?
C19 Fe1 C20 40.2(3) . . ?
C20 Fe1 S1 158.2(2) . . ?
C20 Fe1 S2 118.8(2) . . ?
Ni1 S1 Fe1 91.85(6) . . ?
C2 S1 Ni1 96.60(19) . . ?
C2 S1 Fe1 117.71(19) . . ?
Ni1 S2 Fe1 89.57(5) . . ?
C10 S2 Ni1 109.41(17) . . ?
C10 S2 Fe1 109.00(17) . . ?
C3 N1 Ni1 111.3(3) . . ?
C4 N1 Ni1 104.4(3) . . ?
C4 N1 C3 110.6(4) . . ?
C7 N1 Ni1 107.8(3) . . ?
C7 N1 C3 112.0(4) . . ?
C7 N1 C4 110.4(4) . . ?
C6 N2 Ni1 106.0(3) . . ?
C6 N2 C8 110.1(4) . . ?
C8 N2 Ni1 105.8(3) . . ?
C9 N2 Ni1 116.3(3) . . ?
C9 N2 C6 109.7(4) . . ?
C9 N2 C8 108.8(4) . . ?
O1 C1 Fe1 177.3(5) . . ?
S1 C2 H2A 110.5 . . ?
S1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 S1 106.1(4) . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
N1 C3 C2 109.9(4) . . ?
N1 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
N1 C4 C5 112.6(4) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 115.3(5) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
N2 C6 C5 112.6(4) . . ?
N2 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N1 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
N1 C7 C8 109.5(4) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
N2 C8 C7 110.9(4) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S2 117.1(4) . . ?
C11 C10 C15 120.0(5) . . ?
C15 C10 S2 122.9(4) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(5) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(6) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.3(5) . . ?
C14 C15 H15 120.3 . . ?
Fe1 C16 H16 125.1 . . ?
C17 C16 Fe1 70.0(3) . . ?
C17 C16 H16 125.9 . . ?
C20 C16 Fe1 70.5(4) . . ?
C20 C16 H16 125.9 . . ?
C20 C16 C17 108.1(6) . . ?
Fe1 C17 H17 124.8 . . ?
C16 C17 Fe1 70.4(3) . . ?
C16 C17 H17 125.9 . . ?
C18 C17 Fe1 70.4(3) . . ?
C18 C17 C16 108.1(6) . . ?
C18 C17 H17 125.9 . . ?
Fe1 C18 H18 125.6 . . ?
C17 C18 Fe1 70.1(3) . . ?
C17 C18 H18 125.8 . . ?
C19 C18 Fe1 70.1(3) . . ?
C19 C18 C17 108.5(6) . . ?
C19 C18 H18 125.8 . . ?
Fe1 C19 H19 124.6 . . ?
C18 C19 Fe1 70.4(3) . . ?
C18 C19 H19 126.5 . . ?
C18 C19 C20 107.0(6) . . ?
C20 C19 Fe1 70.1(3) . . ?
C20 C19 H19 126.5 . . ?
Fe1 C20 H20 125.6 . . ?
C16 C20 Fe1 70.4(3) . . ?
C16 C20 C19 108.3(6) . . ?
C16 C20 H20 125.8 . . ?
C19 C20 Fe1 69.7(4) . . ?
C19 C20 H20 125.8 . . ?
F1 B1 F2 107.2(4) . . ?
F1 B1 F3 113.7(3) . . ?
F3 B1 F2 101.9(3) . . ?
F4 B1 F1 114.5(4) . . ?
F4 B1 F2 106.1(6) . . ?
F4 B1 F3 112.1(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
