#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/08/1570858.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1570858
loop_
_publ_author_name
'Ruiz, Sarah E.'
'Arman, Hadi D.'
'Adrian, Rafael A.'
_publ_section_title
;
 Bis[2,6-bis(benzimidazol-2-yl)pyridine-κ3
 N,N′,N′′]nickel(II) bis(trifluoromethanesulfonate)
 diethyl ether monosolvate
;
_journal_coeditor_code           VM4063
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x240088
_journal_paper_doi               10.1107/S2414314624000889
_journal_volume                  9
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          '[Ni (C19 H13 N5)2] (C F3 S O3)2, C4 H10 O'
_chemical_formula_moiety         'C38 H26 N10 Ni 2+, 2(C F3 O3 S -), C4 H10 O'
_chemical_formula_sum            'C44 H36 F6 N10 Ni O7 S2'
_chemical_formula_weight         1053.66
_chemical_name_systematic
'Bis[2,6-bis(benzimidazol-2-yl)pyridine-κ³N,N',N'']nickel(II) bis(trifluoromethanesulfonate) diethyl ether monosolvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.955(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1089(3)
_cell_length_b                   13.3568(3)
_cell_length_c                   14.0513(4)
_cell_measurement_reflns_used    12040
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      73.4530
_cell_measurement_theta_min      3.6760
_cell_volume                     2244.90(10)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11492
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.177
_diffrn_reflns_theta_min         3.184
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_T_max  0.145
_exptl_absorpt_correction_T_min  0.014
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.082
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.275
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         11492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0575
_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)+(0.0500P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1364
_reflns_number_gt                10931
_reflns_number_total             11492
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm4063.cif
_cod_data_source_block           I
_cod_database_code               1570858
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.876
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.50632(10) 0.65435(10) 0.76555(8) 0.0407(3) Uani d 1 . .
S S2 0.12531(15) 0.16821(17) 0.73086(13) 0.0483(5) Uani d 1 . .
S S1 0.56101(15) 0.65885(17) 0.26452(11) 0.0444(4) Uani d 1 . .
F F3 0.4341(4) 0.5038(4) 0.2844(4) 0.0600(13) Uani d 1 . .
F F5 -0.0436(4) 0.2869(4) 0.7412(4) 0.0591(12) Uani d 1 . .
F F1 0.3856(4) 0.6378(5) 0.3527(4) 0.0776(17) Uani d 1 . .
O O6 0.1414(5) 0.0643(5) 0.7476(5) 0.0582(15) Uani d 1 . .
N N2 0.7063(5) 0.6697(5) 0.5513(4) 0.0432(14) Uani d 1 . .
H H2 0.718066 0.642731 0.496620 0.052 Uiso calc 1 . .
N N7 0.7275(5) 0.6077(5) 1.0201(4) 0.0423(14) Uani d 1 . .
H H7 0.755640 0.636859 1.074683 0.051 Uiso calc 1 . .
F F2 0.3508(4) 0.6213(6) 0.1983(4) 0.0850(19) Uani d 1 . .
F F4 -0.0233(5) 0.1658(6) 0.8446(5) 0.104(3) Uani d 1 . .
O O1 0.5401(5) 0.7636(5) 0.2534(4) 0.0581(15) Uani d 1 . .
O O3 0.5901(5) 0.6091(4) 0.1816(4) 0.0490(13) Uani d 1 . .
N N9 0.3994(5) 0.7710(5) 0.7021(4) 0.0415(14) Uani d 1 . .
N N8 0.5189(5) 0.7559(5) 0.8729(4) 0.0398(13) Uani d 1 . .
O O2 0.6271(5) 0.6297(5) 0.3543(4) 0.0552(15) Uani d 1 . .
N N5 0.2661(5) 0.4311(5) 0.7626(4) 0.0433(14) Uani d 1 . .
H H5 0.239063 0.376827 0.731903 0.052 Uiso calc 1 . .
N N6 0.6242(5) 0.5851(5) 0.8767(4) 0.0399(14) Uani d 1 . .
N N1 0.6335(5) 0.6949(5) 0.6854(4) 0.0404(14) Uani d 1 . .
O O4 0.1889(6) 0.2296(6) 0.7993(6) 0.092(3) Uani d 1 . .
C C14 0.2991(6) 0.5575(6) 0.8663(5) 0.0428(16) Uani d 1 . .
C C13 0.3487(6) 0.4907(6) 0.7390(5) 0.0404(16) Uani d 1 . .
N N4 0.3704(5) 0.5680(5) 0.7993(4) 0.0425(14) Uani d 1 . .
N N10 0.3142(5) 0.9148(5) 0.7293(4) 0.0413(14) Uani d 1 . .
H H10 0.294992 0.968015 0.759795 0.050 Uiso calc 1 . .
F F6 -0.0903(4) 0.1373(5) 0.6991(6) 0.110(3) Uani d 1 . .
C C33 0.3290(6) 0.7978(6) 0.6186(5) 0.0428(17) Uani d 1 . .
O O7 1.0079(6) 0.5886(6) 0.6835(5) 0.0737(19) Uani d 1 . .
C C31 0.4549(6) 0.8398(6) 0.8615(5) 0.0397(16) Uani d 1 . .
O O5 0.1204(7) 0.1962(8) 0.6346(6) 0.119(4) Uani d 1 . .
C C9 0.5365(6) 0.4890(6) 0.5125(5) 0.0424(17) Uani d 1 . .
H H9 0.581500 0.492939 0.462963 0.051 Uiso calc 1 . .
C C16 0.2085(7) 0.5847(7) 1.0009(6) 0.052(2) Uani d 1 . .
H H16 0.198024 0.623517 1.055447 0.062 Uiso calc 1 . .
N N3 0.4863(5) 0.5508(5) 0.6588(4) 0.0429(14) Uani d 1 . .
C C30 0.4568(6) 0.9081(6) 0.9357(5) 0.0414(16) Uani d 1 . .
H H30 0.413634 0.967738 0.926984 0.050 Uiso calc 1 . .
C C19 0.2326(6) 0.4718(6) 0.8436(5) 0.0440(17) Uani d 1 . .
C C20 0.6452(6) 0.6446(6) 0.9524(5) 0.0403(16) Uani d 1 . .
C C29 0.5237(7) 0.8875(7) 1.0234(6) 0.0475(19) Uani d 1 . .
H H29 0.524204 0.931933 1.076295 0.057 Uiso calc 1 . .
C C2 0.7176(6) 0.7643(6) 0.6827(5) 0.0419(16) Uani d 1 . .
C C15 0.2872(6) 0.6146(7) 0.9465(5) 0.0469(18) Uani d 1 . .
H H15 0.331897 0.672334 0.963139 0.056 Uiso calc 1 . .
C C32 0.3890(6) 0.8421(6) 0.7656(5) 0.0398(16) Uani d 1 . .
C C26 0.7587(6) 0.5168(6) 0.9879(6) 0.0450(18) Uani d 1 . .
C C3 0.7568(6) 0.8402(6) 0.7474(6) 0.0474(18) Uani d 1 . .
H H3 0.725107 0.850940 0.804352 0.057 Uiso calc 1 . .
C C25 0.8349(7) 0.4442(7) 1.0284(6) 0.0483(19) Uani d 1 . .
H H25 0.879128 0.453552 1.089815 0.058 Uiso calc 1 . .
C C11 0.3895(6) 0.4101(6) 0.5839(5) 0.0438(17) Uani d 1 . .
H H11 0.333945 0.359801 0.583438 0.053 Uiso calc 1 . .
C C34 0.3121(7) 0.7529(7) 0.5277(5) 0.0477(18) Uani d 1 . .
H H34 0.349060 0.692578 0.515659 0.057 Uiso calc 1 . .
C C21 0.6940(6) 0.5033(6) 0.8973(6) 0.0448(18) Uani d 1 . .
C C10 0.4549(7) 0.4157(7) 0.5118(5) 0.0491(19) Uani d 1 . .
H H10A 0.443901 0.368480 0.460650 0.059 Uiso calc 1 . .
C C37 0.1997(7) 0.9344(7) 0.5629(6) 0.0501(19) Uani d 1 . .
H H37 0.161663 0.994138 0.575059 0.060 Uiso calc 1 . .
C C28 0.5898(6) 0.8014(6) 1.0335(5) 0.0409(16) Uani d 1 . .
H H28 0.636807 0.786987 1.092531 0.049 Uiso calc 1 . .
C C38 0.2748(7) 0.8874(6) 0.6343(5) 0.0430(17) Uani d 1 . .
C C12 0.4081(6) 0.4811(6) 0.6571(5) 0.0419(17) Uani d 1 . .
C C36 0.1839(7) 0.8892(7) 0.4742(6) 0.051(2) Uani d 1 . .
H H36 0.133862 0.918901 0.423180 0.061 Uiso calc 1 . .
C C6 0.8510(7) 0.8095(6) 0.5749(6) 0.0473(18) Uani d 1 . .
H H6 0.882512 0.799691 0.517750 0.057 Uiso calc 1 . .
C C7 0.7627(6) 0.7498(6) 0.5978(5) 0.0431(17) Uani d 1 . .
C C5 0.8887(7) 0.8831(7) 0.6409(6) 0.053(2) Uani d 1 . .
H H5A 0.948210 0.925049 0.628445 0.064 Uiso calc 1 . .
C C17 0.1428(7) 0.4987(7) 0.9789(6) 0.0501(19) Uani d 1 . .
H H17 0.090028 0.480291 1.019249 0.060 Uiso calc 1 . .
C C1 0.6294(6) 0.6404(6) 0.6058(5) 0.0404(16) Uani d 1 . .
C C27 0.5854(6) 0.7388(6) 0.9567(5) 0.0399(16) Uani d 1 . .
C C4 0.8430(7) 0.8989(7) 0.7259(6) 0.051(2) Uani d 1 . .
H H4 0.871959 0.950831 0.768849 0.061 Uiso calc 1 . .
C C42 1.0015(8) 0.6461(11) 0.7661(7) 0.074(3) Uani d 1 . .
H H42A 0.983211 0.716507 0.748110 0.088 Uiso calc 1 . .
H H42B 1.073803 0.644660 0.810065 0.088 Uiso calc 1 . .
C C35 0.2398(7) 0.7998(7) 0.4563(6) 0.056(2) Uani d 1 . .
H H35 0.227103 0.771517 0.393543 0.067 Uiso calc 1 . .
C C24 0.8430(7) 0.3586(7) 0.9757(6) 0.052(2) Uani d 1 . .
H H24 0.894924 0.308332 1.000978 0.063 Uiso calc 1 . .
C C39 0.4253(7) 0.6035(8) 0.2760(6) 0.053(2) Uani d 1 . .
C C18 0.1535(7) 0.4407(7) 0.9002(6) 0.0474(18) Uani d 1 . .
H H18 0.109387 0.382328 0.884968 0.057 Uiso calc 1 . .
C C23 0.7766(7) 0.3433(7) 0.8854(7) 0.054(2) Uani d 1 . .
H H23 0.783922 0.282640 0.851552 0.065 Uiso calc 1 . .
C C40 -0.0173(7) 0.1910(7) 0.7536(7) 0.055(2) Uani d 1 . .
C C22 0.7008(7) 0.4149(7) 0.8449(6) 0.0485(19) Uani d 1 . .
H H22 0.655383 0.404490 0.784214 0.058 Uiso calc 1 . .
C C8 0.5495(6) 0.5563(6) 0.5889(5) 0.0427(17) Uani d 1 . .
C C43 1.0938(7) 0.6242(8) 0.6328(7) 0.061(2) Uani d 1 . .
H H43A 1.166897 0.623792 0.675634 0.074 Uiso calc 1 . .
H H43B 1.077298 0.693607 0.610174 0.074 Uiso calc 1 . .
C C44 1.0970(9) 0.5566(9) 0.5495(8) 0.076(3) Uani d 1 . .
H H44A 1.026320 0.561634 0.505107 0.114 Uiso calc 1 . .
H H44B 1.107936 0.487496 0.572428 0.114 Uiso calc 1 . .
H H44C 1.158890 0.576087 0.516031 0.114 Uiso calc 1 . .
C C41 0.9092(9) 0.5999(10) 0.8152(9) 0.093(4) Uani d 1 . .
H H41A 0.837036 0.607265 0.773246 0.140 Uiso calc 1 . .
H H41B 0.906508 0.634276 0.876452 0.140 Uiso calc 1 . .
H H41C 0.924961 0.528713 0.827395 0.140 Uiso calc 1 . .
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'
F F 0.0727 0.0534 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -6 -6 0.0386
-6 -4 4 0.0397
-2 6 6 0.0268
6 3 -5 0.0374
0 -6 -6 0.0327
5 -6 3 0.0521
0 6 6 0.0386
-5 6 -4 0.0059
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N9 Ni1 N6 . . 155.3(2) y
N8 Ni1 N9 . . 78.0(2) y
N8 Ni1 N6 . . 77.4(2) y
N8 Ni1 N1 . . 104.5(2) y
N8 Ni1 N4 . . 99.8(2) y
N8 Ni1 N3 . . 177.3(3) y
N1 Ni1 N9 . . 92.0(2) y
N1 Ni1 N6 . . 92.3(2) y
N1 Ni1 N4 . . 155.8(2) y
N4 Ni1 N9 . . 92.8(2) y
N4 Ni1 N6 . . 93.1(2) y
N3 Ni1 N9 . . 101.2(2) y
N3 Ni1 N6 . . 103.5(2) y
N3 Ni1 N1 . . 78.1(2) y
N3 Ni1 N4 . . 77.7(2) y
O6 S2 C40 . . 104.1(4) ?
O4 S2 O6 . . 114.4(4) ?
O4 S2 C40 . . 102.5(5) ?
O5 S2 O6 . . 114.0(5) ?
O5 S2 O4 . . 116.5(6) ?
O5 S2 C40 . . 103.0(4) ?
O1 S1 O3 . . 115.4(3) ?
O1 S1 O2 . . 115.3(4) ?
O1 S1 C39 . . 105.0(4) ?
O3 S1 O2 . . 114.5(4) ?
O3 S1 C39 . . 102.8(4) ?
O2 S1 C39 . . 101.4(4) ?
C7 N2 H2 . . 126.6 ?
C1 N2 H2 . . 126.6 ?
C1 N2 C7 . . 106.9(6) ?
C20 N7 H7 . . 126.3 ?
C20 N7 C26 . . 107.4(6) ?
C26 N7 H7 . . 126.3 ?
C33 N9 Ni1 . . 142.9(5) ?
C32 N9 Ni1 . . 111.0(5) ?
C32 N9 C33 . . 105.9(6) ?
C31 N8 Ni1 . . 119.5(5) ?
C27 N8 Ni1 . . 120.5(5) ?
C27 N8 C31 . . 120.0(6) ?
C13 N5 H5 . . 126.5 ?
C13 N5 C19 . . 107.0(7) ?
C19 N5 H5 . . 126.5 ?
C20 N6 Ni1 . . 110.4(5) ?
C20 N6 C21 . . 105.7(6) ?
C21 N6 Ni1 . . 143.6(5) ?
C2 N1 Ni1 . . 141.9(5) ?
C1 N1 Ni1 . . 111.9(5) ?
C1 N1 C2 . . 105.9(6) ?
N4 C14 C19 . . 108.9(7) ?
N4 C14 C15 . . 130.9(7) ?
C15 C14 C19 . . 120.2(7) ?
N5 C13 C12 . . 127.9(7) ?
N4 C13 N5 . . 112.2(6) ?
N4 C13 C12 . . 119.8(7) ?
C14 N4 Ni1 . . 142.7(5) ?
C13 N4 Ni1 . . 111.2(5) ?
C13 N4 C14 . . 105.8(6) ?
C32 N10 H10 . . 126.9 ?
C32 N10 C38 . . 106.1(6) ?
C38 N10 H10 . . 126.9 ?
N9 C33 C34 . . 130.2(7) ?
N9 C33 C38 . . 109.3(6) ?
C34 C33 C38 . . 120.3(7) ?
C42 O7 C43 . . 111.6(8) ?
N8 C31 C30 . . 120.9(7) ?
N8 C31 C32 . . 110.3(6) ?
C30 C31 C32 . . 128.8(7) ?
C10 C9 H9 . . 121.4 ?
C8 C9 H9 . . 121.4 ?
C8 C9 C10 . . 117.1(7) ?
C15 C16 H16 . . 118.8 ?
C15 C16 C17 . . 122.4(7) ?
C17 C16 H16 . . 118.8 ?
C12 N3 Ni1 . . 119.7(5) ?
C12 N3 C8 . . 121.0(7) ?
C8 N3 Ni1 . . 119.3(5) ?
C31 C30 H30 . . 120.8 ?
C31 C30 C29 . . 118.4(7) ?
C29 C30 H30 . . 120.8 ?
N5 C19 C14 . . 106.1(7) ?
N5 C19 C18 . . 131.9(8) ?
C18 C19 C14 . . 122.0(7) ?
N7 C20 C27 . . 126.8(7) ?
N6 C20 N7 . . 112.0(7) ?
N6 C20 C27 . . 121.2(6) ?
C30 C29 H29 . . 120.1 ?
C30 C29 C28 . . 119.8(8) ?
C28 C29 H29 . . 120.1 ?
N1 C2 C3 . . 130.3(7) ?
N1 C2 C7 . . 108.5(7) ?
C3 C2 C7 . . 121.2(7) ?
C14 C15 H15 . . 121.2 ?
C16 C15 C14 . . 117.5(8) ?
C16 C15 H15 . . 121.2 ?
N9 C32 N10 . . 112.6(7) ?
N9 C32 C31 . . 120.9(7) ?
N10 C32 C31 . . 126.5(7) ?
N7 C26 C25 . . 132.8(8) ?
N7 C26 C21 . . 105.8(7) ?
C25 C26 C21 . . 121.5(8) ?
C2 C3 H3 . . 121.2 ?
C4 C3 C2 . . 117.6(8) ?
C4 C3 H3 . . 121.2 ?
C26 C25 H25 . . 121.4 ?
C24 C25 C26 . . 117.1(8) ?
C24 C25 H25 . . 121.4 ?
C10 C11 H11 . . 121.3 ?
C10 C11 C12 . . 117.4(7) ?
C12 C11 H11 . . 121.3 ?
C33 C34 H34 . . 121.4 ?
C35 C34 C33 . . 117.2(8) ?
C35 C34 H34 . . 121.4 ?
N6 C21 C26 . . 109.0(7) ?
N6 C21 C22 . . 129.7(7) ?
C26 C21 C22 . . 121.1(8) ?
C9 C10 H10A . . 119.3 ?
C11 C10 C9 . . 121.4(8) ?
C11 C10 H10A . . 119.3 ?
C38 C37 H37 . . 122.0 ?
C36 C37 H37 . . 122.0 ?
C36 C37 C38 . . 116.0(8) ?
C29 C28 H28 . . 120.8 ?
C27 C28 C29 . . 118.4(7) ?
C27 C28 H28 . . 120.8 ?
N10 C38 C33 . . 106.0(7) ?
C37 C38 N10 . . 131.2(8) ?
C37 C38 C33 . . 122.8(7) ?
N3 C12 C13 . . 111.4(7) ?
N3 C12 C11 . . 121.6(7) ?
C11 C12 C13 . . 127.0(7) ?
C37 C36 H36 . . 119.0 ?
C37 C36 C35 . . 122.0(8) ?
C35 C36 H36 . . 119.0 ?
C7 C6 H6 . . 122.2 ?
C5 C6 H6 . . 122.2 ?
C5 C6 C7 . . 115.7(7) ?
N2 C7 C2 . . 106.3(7) ?
N2 C7 C6 . . 132.0(7) ?
C2 C7 C6 . . 121.7(7) ?
C6 C5 H5A . . 118.5 ?
C6 C5 C4 . . 123.0(8) ?
C4 C5 H5A . . 118.5 ?
C16 C17 H17 . . 119.4 ?
C18 C17 C16 . . 121.2(8) ?
C18 C17 H17 . . 119.4 ?
N2 C1 C8 . . 128.3(6) ?
N1 C1 N2 . . 112.3(7) ?
N1 C1 C8 . . 119.3(6) ?
N8 C27 C20 . . 110.3(7) ?
N8 C27 C28 . . 122.4(7) ?
C28 C27 C20 . . 127.3(7) ?
C3 C4 C5 . . 120.9(8) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
O7 C42 H42A . . 110.3 ?
O7 C42 H42B . . 110.3 ?
O7 C42 C41 . . 106.9(10) ?
H42A C42 H42B . . 108.6 ?
C41 C42 H42A . . 110.3 ?
C41 C42 H42B . . 110.3 ?
C34 C35 C36 . . 121.5(8) ?
C34 C35 H35 . . 119.2 ?
C36 C35 H35 . . 119.2 ?
C25 C24 H24 . . 119.0 ?
C25 C24 C23 . . 121.9(8) ?
C23 C24 H24 . . 119.0 ?
F3 C39 S1 . . 110.5(6) ?
F1 C39 S1 . . 112.0(6) ?
F1 C39 F3 . . 107.8(7) ?
F2 C39 S1 . . 111.1(6) ?
F2 C39 F3 . . 106.6(7) ?
F2 C39 F1 . . 108.6(7) ?
C19 C18 H18 . . 121.7 ?
C17 C18 C19 . . 116.7(8) ?
C17 C18 H18 . . 121.7 ?
C24 C23 H23 . . 119.4 ?
C22 C23 C24 . . 121.2(8) ?
C22 C23 H23 . . 119.4 ?
F5 C40 S2 . . 110.6(6) ?
F5 C40 F4 . . 108.7(8) ?
F4 C40 S2 . . 108.6(6) ?
F6 C40 S2 . . 112.4(7) ?
F6 C40 F5 . . 109.3(7) ?
F6 C40 F4 . . 107.0(9) ?
C21 C22 H22 . . 121.5 ?
C23 C22 C21 . . 117.1(8) ?
C23 C22 H22 . . 121.5 ?
C9 C8 C1 . . 127.5(7) ?
N3 C8 C9 . . 121.5(7) ?
N3 C8 C1 . . 111.0(6) ?
O7 C43 H43A . . 110.2 ?
O7 C43 H43B . . 110.2 ?
O7 C43 C44 . . 107.5(9) ?
H43A C43 H43B . . 108.5 ?
C44 C43 H43A . . 110.2 ?
C44 C43 H43B . . 110.2 ?
C43 C44 H44A . . 109.5 ?
C43 C44 H44B . . 109.5 ?
C43 C44 H44C . . 109.5 ?
H44A C44 H44B . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
C42 C41 H41A . . 109.5 ?
C42 C41 H41B . . 109.5 ?
C42 C41 H41C . . 109.5 ?
H41A C41 H41B . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N9 . 2.130(7) y
Ni1 N8 . 2.017(6) y
Ni1 N6 . 2.153(6) y
Ni1 N1 . 2.114(6) y
Ni1 N4 . 2.123(7) y
Ni1 N3 . 2.028(6) y
S2 O6 . 1.416(7) ?
S2 O4 . 1.400(7) ?
S2 O5 . 1.396(7) ?
S2 C40 . 1.829(8) ?
S1 O1 . 1.426(6) ?
S1 O3 . 1.432(6) ?
S1 O2 . 1.438(6) ?
S1 C39 . 1.832(9) ?
F3 C39 . 1.339(11) ?
F5 C40 . 1.325(10) ?
F1 C39 . 1.328(10) ?
N2 H2 . 0.8800 ?
N2 C7 . 1.378(10) ?
N2 C1 . 1.352(9) ?
N7 H7 . 0.8800 ?
N7 C20 . 1.359(9) ?
N7 C26 . 1.369(10) ?
F2 C39 . 1.325(9) ?
F4 C40 . 1.335(10) ?
N9 C33 . 1.385(9) ?
N9 C32 . 1.323(9) ?
N8 C31 . 1.358(10) ?
N8 C27 . 1.339(9) ?
N5 H5 . 0.8800 ?
N5 C13 . 1.359(10) ?
N5 C19 . 1.378(9) ?
N6 C20 . 1.321(9) ?
N6 C21 . 1.384(10) ?
N1 C2 . 1.383(10) ?
N1 C1 . 1.329(9) ?
C14 N4 . 1.381(9) ?
C14 C19 . 1.408(11) ?
C14 C15 . 1.386(11) ?
C13 N4 . 1.334(10) ?
C13 C12 . 1.454(10) ?
N10 H10 . 0.8800 ?
N10 C32 . 1.370(10) ?
N10 C38 . 1.395(9) ?
F6 C40 . 1.293(11) ?
C33 C34 . 1.397(10) ?
C33 C38 . 1.398(11) ?
O7 C42 . 1.404(13) ?
O7 C43 . 1.431(10) ?
C31 C30 . 1.382(10) ?
C31 C32 . 1.456(10) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.390(11) ?
C9 C8 . 1.390(10) ?
C16 H16 . 0.9500 ?
C16 C15 . 1.371(11) ?
C16 C17 . 1.404(12) ?
N3 C12 . 1.325(10) ?
N3 C8 . 1.338(9) ?
C30 H30 . 0.9500 ?
C30 C29 . 1.393(11) ?
C19 C18 . 1.401(11) ?
C20 C27 . 1.457(11) ?
C29 H29 . 0.9500 ?
C29 C28 . 1.396(11) ?
C2 C3 . 1.395(11) ?
C2 C7 . 1.401(10) ?
C15 H15 . 0.9500 ?
C26 C25 . 1.398(11) ?
C26 C21 . 1.398(11) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.377(12) ?
C25 H25 . 0.9500 ?
C25 C24 . 1.374(12) ?
C11 H11 . 0.9500 ?
C11 C10 . 1.382(10) ?
C11 C12 . 1.392(11) ?
C34 H34 . 0.9500 ?
C34 C35 . 1.375(11) ?
C21 C22 . 1.401(11) ?
C10 H10A . 0.9500 ?
C37 H37 . 0.9500 ?
C37 C38 . 1.394(11) ?
C37 C36 . 1.371(11) ?
C28 H28 . 0.9500 ?
C28 C27 . 1.361(10) ?
C36 H36 . 0.9500 ?
C36 C35 . 1.414(12) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.411(11) ?
C6 C5 . 1.379(12) ?
C5 H5A . 0.9500 ?
C5 C4 . 1.408(12) ?
C17 H17 . 0.9500 ?
C17 C18 . 1.372(11) ?
C1 C8 . 1.478(11) ?
C4 H4 . 0.9500 ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C42 C41 . 1.532(14) ?
C35 H35 . 0.9500 ?
C24 H24 . 0.9500 ?
C24 C23 . 1.408(12) ?
C18 H18 . 0.9500 ?
C23 H23 . 0.9500 ?
C23 C22 . 1.385(12) ?
C22 H22 . 0.9500 ?
C43 H43A . 0.9900 ?
C43 H43B . 0.9900 ?
C43 C44 . 1.483(14) ?
C44 H44A . 0.9800 ?
C44 H44B . 0.9800 ?
C44 H44C . 0.9800 ?
C41 H41A . 0.9800 ?
C41 H41B . 0.9800 ?
C41 H41C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O2 . 0.88 2.14 2.836(8) 136 yes
N7 H7 O4 2_657 0.88 2.18 3.052(11) 171 yes
N5 H5 O4 . 0.88 2.31 2.922(11) 127 yes
N10 H10 O6 1_565 0.88 2.25 2.933(9) 135 yes
N10 H10 O3 2_656 0.88 2.41 3.032(9) 128 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ni1 N9 C33 C34 . . . . -10.4(14) ?
Ni1 N9 C33 C38 . . . . 173.4(6) ?
Ni1 N9 C32 N10 . . . . -175.5(5) ?
Ni1 N9 C32 C31 . . . . 6.2(9) ?
Ni1 N8 C31 C30 . . . . 176.3(5) ?
Ni1 N8 C31 C32 . . . . -2.8(8) ?
Ni1 N8 C27 C20 . . . . 3.0(8) ?
Ni1 N8 C27 C28 . . . . -174.8(6) ?
Ni1 N6 C20 N7 . . . . -173.9(5) ?
Ni1 N6 C20 C27 . . . . 4.9(8) ?
Ni1 N6 C21 C26 . . . . 172.7(6) ?
Ni1 N6 C21 C22 . . . . -11.3(14) ?
Ni1 N1 C2 C3 . . . . 5.2(14) ?
Ni1 N1 C2 C7 . . . . -173.5(6) ?
Ni1 N1 C1 N2 . . . . 176.4(5) ?
Ni1 N1 C1 C8 . . . . -6.0(8) ?
Ni1 N3 C12 C13 . . . . -1.6(8) ?
Ni1 N3 C12 C11 . . . . 178.3(6) ?
Ni1 N3 C8 C9 . . . . -177.9(6) ?
Ni1 N3 C8 C1 . . . . 1.9(8) ?
O6 S2 C40 F5 . . . . 179.4(6) ?
O6 S2 C40 F4 . . . . 60.2(8) ?
O6 S2 C40 F6 . . . . -58.1(8) ?
N2 C1 C8 C9 . . . . -0.1(13) ?
N2 C1 C8 N3 . . . . -179.9(7) ?
N7 C20 C27 N8 . . . . 173.2(7) ?
N7 C20 C27 C28 . . . . -9.1(12) ?
N7 C26 C25 C24 . . . . 178.2(8) ?
N7 C26 C21 N6 . . . . -0.7(8) ?
N7 C26 C21 C22 . . . . -177.1(7) ?
O1 S1 C39 F3 . . . . 178.4(5) ?
O1 S1 C39 F1 . . . . -61.4(7) ?
O1 S1 C39 F2 . . . . 60.3(7) ?
O3 S1 C39 F3 . . . . 57.4(6) ?
O3 S1 C39 F1 . . . . 177.5(6) ?
O3 S1 C39 F2 . . . . -60.8(7) ?
N9 C33 C34 C35 . . . . -176.8(8) ?
N9 C33 C38 N10 . . . . 0.1(8) ?
N9 C33 C38 C37 . . . . 179.0(7) ?
N8 C31 C30 C29 . . . . -1.8(11) ?
N8 C31 C32 N9 . . . . -2.6(10) ?
N8 C31 C32 N10 . . . . 179.2(7) ?
O2 S1 C39 F3 . . . . -61.3(6) ?
O2 S1 C39 F1 . . . . 58.9(7) ?
O2 S1 C39 F2 . . . . -179.4(7) ?
N5 C13 N4 Ni1 . . . . 176.5(5) ?
N5 C13 N4 C14 . . . . 0.7(9) ?
N5 C13 C12 N3 . . . . -177.8(7) ?
N5 C13 C12 C11 . . . . 2.3(13) ?
N5 C19 C18 C17 . . . . 178.4(8) ?
N6 C20 C27 N8 . . . . -5.3(10) ?
N6 C20 C27 C28 . . . . 172.3(7) ?
N6 C21 C22 C23 . . . . -177.5(8) ?
N1 C2 C3 C4 . . . . -179.9(8) ?
N1 C2 C7 N2 . . . . -1.4(8) ?
N1 C2 C7 C6 . . . . -179.7(7) ?
N1 C1 C8 C9 . . . . -177.2(7) ?
N1 C1 C8 N3 . . . . 3.0(10) ?
O4 S2 C40 F5 . . . . 60.0(7) ?
O4 S2 C40 F4 . . . . -59.2(8) ?
O4 S2 C40 F6 . . . . -177.5(8) ?
C14 C19 C18 C17 . . . . 0.7(12) ?
C13 N5 C19 C14 . . . . 0.0(9) ?
C13 N5 C19 C18 . . . . -178.0(9) ?
N4 C14 C19 N5 . . . . 0.5(9) ?
N4 C14 C19 C18 . . . . 178.7(7) ?
N4 C14 C15 C16 . . . . -179.4(8) ?
N4 C13 C12 N3 . . . . 5.2(10) ?
N4 C13 C12 C11 . . . . -174.7(7) ?
C33 N9 C32 N10 . . . . 0.6(9) ?
C33 N9 C32 C31 . . . . -177.8(7) ?
C33 C34 C35 C36 . . . . -0.6(13) ?
C31 N8 C27 C20 . . . . 179.7(6) ?
C31 N8 C27 C28 . . . . 1.9(11) ?
C31 C30 C29 C28 . . . . 2.5(11) ?
O5 S2 C40 F5 . . . . -61.3(8) ?
O5 S2 C40 F4 . . . . 179.4(8) ?
O5 S2 C40 F6 . . . . 61.2(9) ?
C16 C17 C18 C19 . . . . -0.1(13) ?
C30 C31 C32 N9 . . . . 178.4(8) ?
C30 C31 C32 N10 . . . . 0.2(13) ?
C30 C29 C28 C27 . . . . -1.1(11) ?
C19 N5 C13 N4 . . . . -0.4(9) ?
C19 N5 C13 C12 . . . . -177.6(7) ?
C19 C14 N4 Ni1 . . . . -174.3(6) ?
C19 C14 N4 C13 . . . . -0.7(9) ?
C19 C14 C15 C16 . . . . -0.6(12) ?
C20 N7 C26 C25 . . . . -177.0(8) ?
C20 N7 C26 C21 . . . . 1.8(8) ?
C20 N6 C21 C26 . . . . -0.7(8) ?
C20 N6 C21 C22 . . . . 175.3(8) ?
C29 C28 C27 N8 . . . . -1.1(11) ?
C29 C28 C27 C20 . . . . -178.5(7) ?
C2 N1 C1 N2 . . . . 0.3(8) ?
C2 N1 C1 C8 . . . . 177.8(6) ?
C2 C3 C4 C5 . . . . 0.6(13) ?
C15 C14 N4 Ni1 . . . . 4.6(15) ?
C15 C14 N4 C13 . . . . 178.2(8) ?
C15 C14 C19 N5 . . . . -178.6(7) ?
C15 C14 C19 C18 . . . . -0.4(12) ?
C15 C16 C17 C18 . . . . -0.9(14) ?
C32 N9 C33 C34 . . . . 175.8(8) ?
C32 N9 C33 C38 . . . . -0.4(8) ?
C32 N10 C38 C33 . . . . 0.2(8) ?
C32 N10 C38 C37 . . . . -178.5(9) ?
C32 C31 C30 C29 . . . . 177.1(7) ?
C26 N7 C20 N6 . . . . -2.4(8) ?
C26 N7 C20 C27 . . . . 178.9(7) ?
C26 C25 C24 C23 . . . . -1.0(13) ?
C26 C21 C22 C23 . . . . -1.9(12) ?
C3 C2 C7 N2 . . . . 179.8(7) ?
C3 C2 C7 C6 . . . . 1.5(12) ?
C25 C26 C21 N6 . . . . 178.3(7) ?
C25 C26 C21 C22 . . . . 1.8(12) ?
C25 C24 C23 C22 . . . . 0.9(13) ?
C34 C33 C38 N10 . . . . -176.5(7) ?
C34 C33 C38 C37 . . . . 2.3(12) ?
C21 N6 C20 N7 . . . . 1.9(8) ?
C21 N6 C20 C27 . . . . -179.3(7) ?
C21 C26 C25 C24 . . . . -0.4(12) ?
C10 C9 C8 N3 . . . . 0.0(11) ?
C10 C9 C8 C1 . . . . -179.8(7) ?
C10 C11 C12 C13 . . . . 179.0(8) ?
C10 C11 C12 N3 . . . . -0.8(11) ?
C37 C36 C35 C34 . . . . 0.8(14) ?
C38 N10 C32 N9 . . . . -0.5(9) ?
C38 N10 C32 C31 . . . . 177.8(7) ?
C38 C33 C34 C35 . . . . -0.9(12) ?
C38 C37 C36 C35 . . . . 0.5(13) ?
C12 C13 N4 Ni1 . . . . -6.1(9) ?
C12 C13 N4 C14 . . . . 178.1(7) ?
C12 N3 C8 C9 . . . . -0.5(11) ?
C12 N3 C8 C1 . . . . 179.3(7) ?
C12 C11 C10 C9 . . . . 0.3(12) ?
C36 C37 C38 N10 . . . . 176.4(8) ?
C36 C37 C38 C33 . . . . -2.0(12) ?
C6 C5 C4 C3 . . . . 0.1(14) ?
C7 N2 C1 N1 . . . . -1.2(8) ?
C7 N2 C1 C8 . . . . -178.4(7) ?
C7 C2 C3 C4 . . . . -1.4(12) ?
C7 C6 C5 C4 . . . . -0.1(12) ?
C5 C6 C7 N2 . . . . -178.5(8) ?
C5 C6 C7 C2 . . . . -0.7(11) ?
C17 C16 C15 C14 . . . . 1.2(13) ?
C1 N2 C7 C2 . . . . 1.5(8) ?
C1 N2 C7 C6 . . . . 179.6(8) ?
C1 N1 C2 C3 . . . . 179.4(8) ?
C1 N1 C2 C7 . . . . 0.7(8) ?
C27 N8 C31 C30 . . . . -0.4(11) ?
C27 N8 C31 C32 . . . . -179.5(6) ?
C42 O7 C43 C44 . . . . 177.8(8) ?
C24 C23 C22 C21 . . . . 0.6(12) ?
C8 C9 C10 C11 . . . . 0.1(12) ?
C8 N3 C12 C13 . . . . -178.9(7) ?
C8 N3 C12 C11 . . . . 1.0(11) ?
C43 O7 C42 C41 . . . . -178.8(8) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5896 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 0.4104 1.0002 0.0004 0.2669 0.0004 -1.0000 -0.0003 -0.0017 0.0002 -1.0003
