1-(2-Bromo­benzyl)­pyridinium bis­(maleodi­nitrile­di­thiol­ato)­nickelate(III)

Ren, X.-M.; Xie, J.-L.; Li, Y.-Z.; Meng, Q.-J.

doi:10.1107/S1600536803025182

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1-(2-Bromobenzyl)pyridinium bis(maleodinitriledithiolato)nickelate(III)

X.-M. Ren, J.-L. Xie, Y.-Z. Li and Q.-J. Meng

In the title compound, (C₁₂H₁₁BrN)[Ni(C₄N₂S₂)₂], completely segregated columnar stacks of anions and cations are observed. There are three symmetry-independent anions in the asymmetric unit (A, B and C), all of them essentially planar. Two types of anionic columns are both stacked along the b axis of the crystal; columns of the first type are made up entirely of one of the three independent anions (anion A) and have identical Ni

Ni distances of 4.1401 (10) Å, while columns of the second type are made up of alternating anions B and C and have slightly different, alternating Ni

Ni distances [4.1695 (11) and 4.0971 (11) Å]. The columns of Λ-shaped bromobenzylpyridinium cations show no π–π interactions within the stack; there are, however, short S

Br contacts between the anionic and cationic stacks.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025182/ya6181sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025182/ya6181Isup2.hkl Contains datablock I

CCDC reference: 227745

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.047
wR factor = 0.120
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2       =       1.48 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C4       =       1.48 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5     -   C6       =       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7     -   C8       =       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1'    -   C2'      =       1.49 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3'    -   C4'      =       1.48 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5'    -   C6'      =       1.49 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7'    -   C8'      =       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1"    -   C2"      =       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3"    -   C4"      =       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5"    -   C6"      =       1.49 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7"    -   C8"      =       1.47 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  S4       =       3.59 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1'   ..  S2"      =       3.59 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

(C₁₂H₁₁BrN)[Ni(C₄N₂S₂)₂]	F(000) = 3516
M_r = 588.20	D_x = 1.705 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 863 reflections
a = 31.400 (6) Å	θ = 2.8–22.3°
b = 6.9700 (14) Å	µ = 2.97 mm⁻¹
c = 33.760 (7) Å	T = 293 K
β = 111.50 (3)°	Block, brown
V = 6875 (2) Å³	0.3 × 0.2 × 0.2 mm
Z = 12

Data collection top

Bruker SMART CCD area-detector diffractometer	12054 independent reflections
Radiation source: fine-focus sealed tube	7095 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −37→34
T_min = 0.50, T_max = 0.55	k = −8→7
33754 measured reflections	l = −30→40

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.055P)²] where P = (F_o² + 2F_c²)/3
12054 reflections	(Δ/σ)_max = 0.001
838 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.474060 (18)	0.60757 (8)	0.716830 (17)	0.04841 (17)
Br1	0.345920 (17)	0.03235 (7)	0.669170 (16)	0.06507 (17)
C1	0.48386 (17)	0.6266 (7)	0.58146 (16)	0.0671 (14)
C2	0.47120 (16)	0.6257 (6)	0.61954 (15)	0.0570 (12)
C3	0.42916 (16)	0.6323 (6)	0.61413 (14)	0.0564 (12)
C4	0.39671 (16)	0.6502 (7)	0.56952 (16)	0.0615 (13)
C5	0.46946 (16)	0.6029 (7)	0.85462 (16)	0.0593 (13)
C6	0.47985 (16)	0.6045 (6)	0.81551 (14)	0.0532 (12)
C7	0.52143 (16)	0.6126 (6)	0.81969 (14)	0.0510 (12)
C8	0.55527 (16)	0.6167 (7)	0.86333 (15)	0.0540 (12)
N5	0.28779 (13)	0.1954 (6)	0.55855 (11)	0.0540 (10)
C9	0.30364 (17)	0.0286 (7)	0.54827 (14)	0.0623 (13)
H9A	0.3344	−0.0021	0.5617	0.075*
C10	0.2754 (2)	−0.0968 (7)	0.51848 (16)	0.0700 (15)
H10A	0.2868	−0.2098	0.5116	0.084*
C11	0.23098 (18)	−0.0511 (8)	0.49976 (16)	0.0685 (15)
H11A	0.2111	−0.1348	0.4802	0.082*
C12	0.21534 (17)	0.1135 (8)	0.50901 (15)	0.0672 (14)
H12A	0.1847	0.1460	0.4951	0.081*
C13	0.24406 (16)	0.2371 (7)	0.53918 (15)	0.0618 (13)
H13A	0.2324	0.3502	0.5458	0.074*
C14	0.31825 (14)	0.3399 (6)	0.59162 (13)	0.0561 (12)
H14A	0.3494	0.2922	0.6012	0.067*
H14B	0.3177	0.4597	0.5768	0.067*
C15	0.30760 (15)	0.3860 (7)	0.63071 (15)	0.0560 (12)
C16	0.31872 (14)	0.2679 (7)	0.66676 (15)	0.0560 (12)
C17	0.30898 (15)	0.3234 (7)	0.70225 (15)	0.0624 (13)
H17A	0.3161	0.2428	0.7258	0.075*
C18	0.28900 (16)	0.4966 (8)	0.70210 (16)	0.0677 (15)
H18A	0.2825	0.5365	0.7255	0.081*
C19	0.27838 (16)	0.6143 (7)	0.66594 (18)	0.0681 (14)
H19A	0.2649	0.7331	0.6661	0.082*
C20	0.28690 (16)	0.5623 (7)	0.63084 (16)	0.0625 (13)
H20A	0.2790	0.6429	0.6073	0.075*
N1	0.49214 (15)	0.6326 (6)	0.54877 (13)	0.0818 (14)
N2	0.37076 (14)	0.6718 (6)	0.53382 (13)	0.0715 (12)
N3	0.46184 (14)	0.5979 (6)	0.88784 (13)	0.0724 (12)
N4	0.58251 (13)	0.6280 (6)	0.89823 (12)	0.0621 (11)
S1	0.50992 (4)	0.60699 (17)	0.67288 (4)	0.0534 (3)
S2	0.41421 (4)	0.62238 (17)	0.66027 (4)	0.0544 (3)
S3	0.43995 (4)	0.60121 (17)	0.76251 (4)	0.0542 (3)
S4	0.53451 (4)	0.61006 (17)	0.77223 (4)	0.0509 (3)
Ni1'	0.139360 (18)	0.55847 (8)	0.719000 (17)	0.04787 (17)
Br1'	1.014390 (16)	−0.00292 (7)	0.664920 (15)	0.06030 (16)
C1'	0.15637 (16)	0.5677 (7)	0.58645 (15)	0.0581 (13)
C2'	0.14131 (16)	0.5724 (6)	0.62333 (14)	0.0515 (12)
C3'	0.09895 (16)	0.5853 (6)	0.61540 (14)	0.0528 (12)
C4'	0.06840 (16)	0.6043 (6)	0.57030 (16)	0.0560 (13)
C5'	0.12807 (16)	0.5401 (7)	0.85376 (16)	0.0579 (13)
C6'	0.14205 (15)	0.5424 (6)	0.81622 (14)	0.0508 (12)
C7'	0.18341 (15)	0.5495 (6)	0.82224 (14)	0.0494 (11)
C8'	0.21562 (16)	0.5494 (6)	0.86652 (15)	0.0534 (12)
N5'	0.95862 (12)	0.1540 (6)	0.55439 (11)	0.0531 (10)
C9'	0.97616 (16)	−0.0100 (7)	0.54424 (14)	0.0586 (13)
H9'	1.0073	−0.0346	0.5572	0.070*
C10'	0.94889 (18)	−0.1388 (7)	0.51548 (15)	0.0656 (14)
H10'	0.9612	−0.2504	0.5090	0.079*
C11'	0.90396 (18)	−0.1009 (7)	0.49676 (15)	0.0671 (14)
H11'	0.8848	−0.1871	0.4773	0.081*
C12'	0.88689 (16)	0.0617 (7)	0.50628 (16)	0.0660 (14)
H12'	0.8559	0.0889	0.4929	0.079*
C13'	0.91452 (16)	0.1881 (7)	0.53550 (15)	0.0603 (13)
H13'	0.9020	0.2991	0.5421	0.072*
C14'	0.98701 (15)	0.3023 (7)	0.58717 (14)	0.0602 (13)
H14C	1.0186	0.2597	0.5970	0.072*
H14D	0.9855	0.4215	0.5719	0.072*
C15'	0.97659 (16)	0.3505 (7)	0.62635 (16)	0.0601 (13)
C16'	0.98694 (15)	0.2301 (7)	0.66233 (16)	0.0601 (13)
C17'	0.97695 (15)	0.2880 (7)	0.69771 (15)	0.0603 (13)
H17'	0.9841	0.2083	0.7214	0.072*
C18'	0.95668 (15)	0.4619 (7)	0.69737 (16)	0.0603 (13)
H18'	0.9496	0.5015	0.7206	0.072*
C19'	0.94682 (15)	0.5782 (7)	0.66175 (17)	0.0667 (14)
H19'	0.9334	0.6972	0.6616	0.080*
C20'	0.95633 (15)	0.5234 (7)	0.62634 (16)	0.0589 (13)
H20'	0.9489	0.6039	0.6028	0.071*
N1'	0.16946 (14)	0.5624 (6)	0.55737 (13)	0.0727 (12)
N2'	0.04408 (13)	0.6210 (6)	0.53409 (12)	0.0638 (11)
N3'	0.11907 (14)	0.5319 (6)	0.88614 (13)	0.0703 (12)
N4'	0.24211 (13)	0.5520 (5)	0.90149 (12)	0.0588 (10)
S1'	0.17784 (4)	0.55630 (16)	0.67783 (4)	0.0510 (3)
S2'	0.08122 (4)	0.57971 (16)	0.66004 (4)	0.0515 (3)
S3'	0.10275 (4)	0.54528 (17)	0.76232 (4)	0.0537 (3)
S4'	0.19849 (4)	0.55547 (16)	0.77611 (4)	0.0511 (3)
Ni1"	0.192510 (18)	0.05231 (8)	0.784200 (17)	0.04811 (16)
Br1"	0.319000 (17)	0.48846 (7)	0.836120 (15)	0.06405 (16)
C1"	0.20421 (16)	0.0687 (6)	0.64898 (15)	0.0562 (13)
C2"	0.19071 (15)	0.0624 (6)	0.68642 (14)	0.0508 (12)
C3"	0.14889 (15)	0.0649 (6)	0.68090 (14)	0.0504 (12)
C4"	0.11656 (15)	0.0738 (6)	0.63666 (15)	0.0513 (12)
C5"	0.17321 (16)	0.0282 (7)	0.91559 (16)	0.0625 (14)
C6"	0.18940 (16)	0.0447 (6)	0.87949 (14)	0.0534 (12)
C7"	0.23150 (16)	0.0535 (6)	0.88781 (14)	0.0514 (12)
C8"	0.26116 (16)	0.0658 (7)	0.93298 (16)	0.0594 (13)
N5"	0.37064 (13)	0.6023 (6)	0.94694 (12)	0.0589 (11)
C9"	0.41592 (18)	0.6078 (8)	0.95923 (16)	0.0761 (16)
H9"	0.4298	0.7063	0.9498	0.091*
C10"	0.4420 (2)	0.4714 (9)	0.98534 (18)	0.0899 (19)
H10"	0.4685	0.4071	0.9925	0.108*
C11"	0.4226 (2)	0.3224 (8)	0.99876 (16)	0.0806 (17)
H11"	0.4407	0.2268	1.0160	0.097*
C12"	0.37705 (18)	0.3158 (7)	0.98680 (15)	0.0659 (14)
H12"	0.3630	0.2169	0.9960	0.079*
C13"	0.35165 (16)	0.4565 (7)	0.96096 (15)	0.0595 (13)
H13"	0.3200	0.4520	0.9526	0.071*
C14"	0.34679 (15)	0.7708 (7)	0.91726 (15)	0.0650 (14)
H14E	0.3142	0.7440	0.9069	0.078*
H14F	0.3516	0.8837	0.9352	0.078*
C15"	0.35753 (16)	0.8282 (7)	0.87947 (17)	0.0648 (14)
C16"	0.34689 (15)	0.7205 (7)	0.84157 (17)	0.0648 (14)
C17"	0.35793 (15)	0.7891 (7)	0.80766 (16)	0.0649 (14)
H17"	0.3509	0.7164	0.7830	0.078*
C18"	0.37881 (16)	0.9607 (7)	0.81063 (17)	0.0650 (14)
H18"	0.3860	1.0074	0.7880	0.078*
C19"	0.38938 (16)	1.0661 (7)	0.84767 (18)	0.0707 (15)
H19"	0.4040	1.1839	0.8498	0.085*
C20"	0.37870 (16)	1.0000 (7)	0.88191 (16)	0.0645 (14)
H20"	0.3861	1.0739	0.9065	0.077*
N1"	0.21359 (13)	0.0710 (6)	0.61723 (13)	0.0684 (12)
N2"	0.08969 (13)	0.0831 (5)	0.60189 (12)	0.0570 (10)
N3"	0.15875 (14)	0.0153 (6)	0.94331 (13)	0.0742 (13)
N4"	0.28278 (13)	0.0688 (6)	0.97004 (12)	0.0657 (12)
S1"	0.22936 (4)	0.05474 (17)	0.74102 (4)	0.0537 (3)
S2"	0.13372 (4)	0.05791 (16)	0.72699 (3)	0.0505 (3)
S3"	0.15323 (4)	0.04230 (17)	0.82445 (4)	0.0523 (3)
S4"	0.25004 (4)	0.06031 (17)	0.84380 (4)	0.0542 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0442 (3)	0.0495 (4)	0.0516 (4)	0.0004 (3)	0.0177 (3)	−0.0005 (3)
Br1	0.0610 (3)	0.0671 (3)	0.0648 (4)	0.0007 (3)	0.0204 (3)	0.0060 (3)
C1	0.067 (4)	0.078 (4)	0.057 (3)	−0.014 (3)	0.024 (3)	−0.013 (3)
C2	0.059 (3)	0.057 (3)	0.061 (3)	−0.003 (2)	0.029 (3)	−0.002 (3)
C3	0.050 (3)	0.061 (3)	0.056 (3)	−0.006 (2)	0.017 (3)	0.000 (3)
C4	0.056 (3)	0.071 (4)	0.056 (3)	−0.010 (3)	0.019 (3)	−0.001 (3)
C5	0.055 (3)	0.064 (3)	0.060 (3)	0.007 (2)	0.023 (3)	0.003 (3)
C6	0.053 (3)	0.054 (3)	0.056 (3)	0.002 (2)	0.025 (3)	0.003 (2)
C7	0.054 (3)	0.047 (3)	0.052 (3)	0.004 (2)	0.021 (3)	−0.002 (2)
C8	0.054 (3)	0.058 (3)	0.052 (3)	0.005 (2)	0.022 (3)	0.001 (3)
N5	0.048 (3)	0.063 (3)	0.052 (2)	0.001 (2)	0.021 (2)	0.003 (2)
C9	0.057 (3)	0.074 (4)	0.051 (3)	−0.003 (3)	0.014 (3)	0.002 (3)
C10	0.086 (4)	0.067 (4)	0.065 (4)	0.001 (3)	0.038 (3)	−0.009 (3)
C11	0.058 (4)	0.077 (4)	0.066 (4)	−0.013 (3)	0.018 (3)	−0.011 (3)
C12	0.052 (3)	0.085 (4)	0.065 (4)	−0.001 (3)	0.021 (3)	−0.004 (3)
C13	0.060 (3)	0.068 (3)	0.066 (3)	0.004 (3)	0.033 (3)	0.001 (3)
C14	0.048 (3)	0.068 (3)	0.056 (3)	−0.009 (2)	0.024 (2)	−0.004 (3)
C15	0.048 (3)	0.068 (3)	0.056 (3)	−0.009 (2)	0.024 (2)	−0.004 (3)
C16	0.048 (3)	0.068 (3)	0.056 (3)	−0.009 (2)	0.024 (3)	−0.004 (3)
C17	0.054 (3)	0.071 (4)	0.058 (3)	0.002 (3)	0.015 (3)	0.006 (3)
C18	0.054 (3)	0.086 (4)	0.065 (4)	−0.003 (3)	0.024 (3)	−0.020 (3)
C19	0.055 (3)	0.063 (3)	0.086 (4)	0.000 (3)	0.025 (3)	−0.001 (3)
C20	0.060 (3)	0.070 (4)	0.061 (4)	−0.010 (3)	0.026 (3)	0.005 (3)
N1	0.091 (3)	0.094 (3)	0.072 (3)	−0.020 (3)	0.043 (3)	−0.015 (3)
N2	0.064 (3)	0.089 (3)	0.056 (3)	−0.017 (2)	0.015 (2)	0.002 (2)
N3	0.071 (3)	0.085 (3)	0.066 (3)	0.012 (2)	0.031 (2)	0.008 (3)
N4	0.059 (3)	0.072 (3)	0.055 (3)	0.007 (2)	0.020 (2)	0.003 (2)
S1	0.0482 (7)	0.0582 (8)	0.0563 (8)	−0.0010 (6)	0.0220 (6)	−0.0018 (6)
S2	0.0458 (7)	0.0608 (8)	0.0548 (8)	−0.0022 (6)	0.0161 (6)	0.0006 (6)
S3	0.0475 (7)	0.0601 (8)	0.0569 (8)	0.0033 (6)	0.0212 (6)	0.0016 (6)
S4	0.0451 (7)	0.0546 (7)	0.0526 (8)	0.0018 (5)	0.0173 (6)	0.0005 (6)
Ni1'	0.0426 (4)	0.0493 (4)	0.0512 (4)	0.0006 (3)	0.0165 (3)	−0.0008 (3)
Br1'	0.0574 (3)	0.0613 (3)	0.0606 (3)	0.0033 (2)	0.0198 (2)	0.0058 (2)
C1'	0.053 (3)	0.065 (3)	0.051 (3)	0.002 (2)	0.013 (3)	−0.004 (3)
C2'	0.056 (3)	0.045 (3)	0.058 (3)	0.003 (2)	0.026 (3)	0.000 (2)
C3'	0.055 (3)	0.052 (3)	0.050 (3)	−0.002 (2)	0.017 (3)	−0.002 (2)
C4'	0.056 (3)	0.056 (3)	0.056 (3)	−0.007 (2)	0.021 (3)	−0.002 (3)
C5'	0.053 (3)	0.059 (3)	0.062 (3)	−0.002 (2)	0.021 (3)	−0.001 (3)
C6'	0.053 (3)	0.049 (3)	0.053 (3)	−0.001 (2)	0.024 (2)	−0.001 (2)
C7'	0.050 (3)	0.050 (3)	0.048 (3)	−0.003 (2)	0.018 (2)	−0.001 (2)
C8'	0.052 (3)	0.056 (3)	0.055 (3)	0.005 (2)	0.022 (3)	0.004 (3)
N5'	0.043 (2)	0.065 (3)	0.052 (3)	−0.003 (2)	0.019 (2)	0.006 (2)
C9'	0.057 (3)	0.062 (3)	0.054 (3)	0.001 (3)	0.016 (3)	−0.001 (3)
C10'	0.075 (4)	0.066 (3)	0.059 (3)	0.005 (3)	0.029 (3)	−0.008 (3)
C11'	0.069 (4)	0.071 (4)	0.059 (3)	−0.018 (3)	0.020 (3)	−0.013 (3)
C12'	0.047 (3)	0.075 (4)	0.070 (4)	−0.007 (3)	0.015 (3)	−0.004 (3)
C13'	0.059 (3)	0.064 (3)	0.066 (3)	0.003 (3)	0.033 (3)	0.001 (3)
C14'	0.059 (3)	0.064 (3)	0.066 (3)	0.003 (2)	0.033 (3)	0.001 (3)
C15'	0.059 (3)	0.064 (3)	0.066 (4)	0.003 (3)	0.033 (3)	0.001 (3)
C16'	0.059 (3)	0.064 (3)	0.066 (3)	0.003 (2)	0.033 (3)	0.001 (3)
C17'	0.059 (3)	0.064 (3)	0.066 (4)	0.003 (3)	0.033 (3)	0.001 (3)
C18'	0.059 (3)	0.064 (3)	0.066 (4)	0.003 (3)	0.033 (3)	0.001 (3)
C19'	0.056 (3)	0.058 (3)	0.086 (4)	0.003 (2)	0.026 (3)	−0.001 (3)
C20'	0.054 (3)	0.059 (3)	0.067 (3)	−0.005 (2)	0.026 (3)	0.008 (3)
N1'	0.075 (3)	0.089 (3)	0.060 (3)	0.006 (2)	0.031 (2)	−0.001 (3)
N2'	0.057 (3)	0.076 (3)	0.055 (3)	−0.012 (2)	0.017 (2)	0.004 (2)
N3'	0.070 (3)	0.084 (3)	0.062 (3)	0.000 (2)	0.030 (2)	−0.002 (2)
N4'	0.054 (3)	0.068 (3)	0.055 (3)	0.000 (2)	0.020 (2)	−0.001 (2)
S1'	0.0448 (7)	0.0558 (7)	0.0532 (7)	0.0018 (5)	0.0190 (6)	0.0002 (6)
S2'	0.0438 (7)	0.0563 (7)	0.0523 (8)	−0.0017 (5)	0.0152 (6)	−0.0003 (6)
S3'	0.0461 (7)	0.0605 (8)	0.0555 (8)	0.0011 (6)	0.0196 (6)	−0.0017 (6)
S4'	0.0442 (7)	0.0562 (7)	0.0513 (7)	0.0015 (5)	0.0157 (6)	0.0009 (6)
Ni1"	0.0436 (4)	0.0503 (4)	0.0498 (4)	0.0002 (3)	0.0163 (3)	0.0010 (3)
Br1"	0.0590 (3)	0.0701 (4)	0.0620 (3)	−0.0046 (2)	0.0208 (3)	−0.0059 (3)
C1"	0.059 (3)	0.059 (3)	0.056 (3)	0.001 (2)	0.027 (3)	0.004 (3)
C2"	0.047 (3)	0.048 (3)	0.055 (3)	0.001 (2)	0.016 (2)	0.004 (2)
C3"	0.050 (3)	0.046 (3)	0.053 (3)	0.000 (2)	0.016 (2)	0.002 (2)
C4"	0.049 (3)	0.053 (3)	0.054 (3)	−0.002 (2)	0.021 (3)	0.003 (2)
C5"	0.056 (3)	0.073 (4)	0.057 (3)	−0.003 (3)	0.020 (3)	0.006 (3)
C6"	0.051 (3)	0.054 (3)	0.056 (3)	0.003 (2)	0.021 (3)	0.006 (2)
C7"	0.050 (3)	0.054 (3)	0.047 (3)	0.004 (2)	0.014 (2)	0.003 (2)
C8"	0.058 (3)	0.065 (3)	0.056 (3)	0.008 (3)	0.022 (3)	0.004 (3)
N5"	0.045 (3)	0.079 (3)	0.054 (3)	0.006 (2)	0.020 (2)	−0.004 (2)
C9"	0.065 (4)	0.097 (4)	0.077 (4)	−0.004 (3)	0.039 (3)	0.014 (3)
C10"	0.072 (4)	0.107 (5)	0.093 (5)	0.026 (4)	0.032 (3)	0.041 (4)
C11"	0.080 (4)	0.092 (5)	0.067 (4)	0.027 (3)	0.023 (3)	0.017 (3)
C12"	0.073 (4)	0.068 (4)	0.057 (3)	0.002 (3)	0.025 (3)	0.003 (3)
C13"	0.048 (3)	0.071 (3)	0.059 (3)	−0.002 (3)	0.019 (3)	−0.001 (3)
C14"	0.057 (3)	0.063 (3)	0.074 (4)	0.003 (3)	0.023 (3)	−0.014 (3)
C15"	0.057 (3)	0.063 (4)	0.074 (4)	0.003 (3)	0.023 (3)	−0.014 (3)
C16"	0.057 (3)	0.063 (3)	0.074 (4)	0.003 (3)	0.023 (3)	−0.014 (3)
C17"	0.057 (3)	0.063 (4)	0.074 (4)	0.003 (3)	0.023 (3)	−0.014 (3)
C18"	0.057 (3)	0.063 (4)	0.074 (4)	0.003 (3)	0.023 (3)	−0.014 (3)
C19"	0.059 (3)	0.064 (3)	0.092 (4)	−0.008 (3)	0.031 (3)	−0.006 (3)
C20"	0.064 (3)	0.075 (4)	0.062 (3)	0.004 (3)	0.032 (3)	−0.012 (3)
N1"	0.069 (3)	0.076 (3)	0.065 (3)	0.000 (2)	0.030 (2)	0.003 (2)
N2"	0.052 (3)	0.068 (3)	0.050 (3)	0.002 (2)	0.017 (2)	0.003 (2)
N3"	0.067 (3)	0.094 (3)	0.063 (3)	−0.008 (2)	0.026 (2)	0.005 (3)
N4"	0.055 (3)	0.082 (3)	0.057 (3)	0.016 (2)	0.017 (2)	−0.003 (2)
S1"	0.0474 (7)	0.0592 (8)	0.0558 (8)	−0.0006 (6)	0.0206 (6)	0.0021 (6)
S2"	0.0447 (7)	0.0554 (7)	0.0503 (7)	−0.0011 (5)	0.0163 (6)	0.0001 (6)
S3"	0.0455 (7)	0.0594 (7)	0.0531 (7)	−0.0005 (6)	0.0191 (6)	0.0019 (6)
S4"	0.0451 (7)	0.0614 (8)	0.0542 (8)	0.0023 (6)	0.0161 (6)	−0.0011 (6)

Geometric parameters (Å, º) top

Ni1—S1	2.1666 (13)	C9'—C10'	1.368 (6)
Ni1—S2	2.1350 (15)	C9'—H9'	0.9300
Ni1—S3	2.1767 (14)	C10'—C11'	1.344 (6)
Ni1—S4	2.1211 (14)	C10'—H10'	0.9300
Br1—C16	1.838 (5)	C11'—C12'	1.342 (6)
C1—N1	1.224 (6)	C11'—H11'	0.9300
C1—C2	1.478 (6)	C12'—C13'	1.369 (6)
C2—C3	1.265 (6)	C12'—H12'	0.9300
C2—S1	1.770 (5)	C13'—H13'	0.9300
C3—C4	1.482 (6)	C14'—C15'	1.512 (6)
C3—S2	1.785 (5)	C14'—H14C	0.9700
C4—N2	1.191 (5)	C14'—H14D	0.9700
C5—N3	1.230 (6)	C15'—C20'	1.363 (6)
C5—C6	1.472 (6)	C15'—C16'	1.413 (6)
C6—C7	1.262 (5)	C16'—C17'	1.401 (6)
C6—S3	1.769 (5)	C17'—C18'	1.368 (6)
C7—C8	1.467 (6)	C17'—H17'	0.9300
C7—S4	1.794 (5)	C18'—C19'	1.388 (6)
C8—N4	1.178 (5)	C18'—H18'	0.9300
N5—C13	1.319 (5)	C19'—C20'	1.388 (6)
N5—C9	1.359 (5)	C19'—H19'	0.9300
N5—C14	1.547 (5)	C20'—H20'	0.9300
C9—C10	1.381 (6)	Ni1"—S1"	2.1681 (13)
C9—H9A	0.9300	Ni1"—S2"	2.1275 (15)
C10—C11	1.341 (6)	Ni1"—S3"	2.1450 (13)
C10—H10A	0.9300	Ni1"—S4"	2.1565 (15)
C11—C12	1.329 (6)	Br1"—C16"	1.816 (5)
C11—H11A	0.9300	C1"—N1"	1.211 (5)
C12—C13	1.386 (6)	C1"—C2"	1.474 (6)
C12—H12A	0.9210	C2"—C3"	1.257 (5)
C13—H13A	0.9300	C2"—S1"	1.798 (4)
C14—C15	1.510 (6)	C3"—C4"	1.468 (6)
C14—H14A	0.9700	C3"—S2"	1.787 (5)
C14—H14B	0.9700	C4"—N2"	1.170 (5)
C15—C20	1.391 (6)	C5"—N3"	1.184 (6)
C15—C16	1.403 (6)	C5"—C6"	1.487 (6)
C16—C17	1.396 (6)	C6"—C7"	1.248 (6)
C17—C18	1.360 (6)	C6"—S3"	1.788 (5)
C17—H17A	0.9300	C7"—C8"	1.469 (6)
C18—C19	1.406 (6)	C7"—S4"	1.784 (5)
C18—H18A	0.9300	C8"—N4"	1.185 (5)
C19—C20	1.356 (6)	N5"—C9"	1.328 (5)
C19—H19A	0.9300	N5"—C13"	1.349 (5)
C20—H20A	0.9300	N5"—C14"	1.547 (5)
Ni1'—S1'	2.1501 (13)	C9"—C10"	1.350 (7)
Ni1'—S2'	2.1571 (15)	C9"—H9"	0.9300
Ni1'—S3'	2.1682 (14)	C10"—C11"	1.363 (7)
Ni1'—S4'	2.1310 (15)	C10"—H10"	0.8975
Br1'—C16'	1.826 (5)	C11"—C12"	1.335 (6)
C1'—N1'	1.196 (5)	C11"—H11"	0.9300
C1'—C2'	1.485 (6)	C12"—C13"	1.360 (6)
C2'—C3'	1.260 (6)	C12"—H12"	0.9300
C2'—S1'	1.779 (5)	C13"—H13"	0.9300
C3'—C4'	1.478 (6)	C14"—C15"	1.489 (6)
C3'—S2'	1.788 (5)	C14"—H14E	0.9700
C4'—N2'	1.186 (5)	C14"—H14F	0.9700
C5'—N3'	1.227 (6)	C15"—C20"	1.357 (6)
C5'—C6'	1.486 (6)	C15"—C16"	1.414 (6)
C6'—C7'	1.240 (5)	C16"—C17"	1.396 (6)
C6'—S3'	1.786 (5)	C17"—C18"	1.350 (6)
C7'—C8'	1.466 (6)	C17"—H17"	0.9300
C7'—S4'	1.787 (4)	C18"—C19"	1.382 (6)
C8'—N4'	1.169 (5)	C18"—H18"	0.9300
N5'—C13'	1.317 (5)	C19"—C20"	1.395 (6)
N5'—C9'	1.366 (5)	C19"—H19"	0.9300
N5'—C14'	1.538 (5)	C20"—H20"	0.9300

S4—Ni1—S2	176.51 (5)	C11'—C12'—C13'	120.9 (5)
S4—Ni1—S1	94.71 (5)	C11'—C12'—H12'	120.1
S2—Ni1—S1	84.01 (5)	C13'—C12'—H12'	119.0
S4—Ni1—S3	83.63 (5)	N5'—C13'—C12'	120.6 (5)
S2—Ni1—S3	97.71 (5)	N5'—C13'—H13'	119.7
S1—Ni1—S3	177.90 (5)	C12'—C13'—H13'	119.7
N1—C1—C2	176.5 (6)	C15'—C14'—N5'	121.6 (4)
C3—C2—C1	118.2 (5)	C15'—C14'—H14C	106.9
C3—C2—S1	116.2 (4)	N5'—C14'—H14C	106.9
C1—C2—S1	125.6 (4)	C15'—C14'—H14D	106.9
C2—C3—C4	116.2 (5)	N5'—C14'—H14D	106.9
C2—C3—S2	117.8 (4)	H14C—C14'—H14D	106.7
C4—C3—S2	126.0 (4)	C20'—C15'—C16'	119.1 (4)
N2—C4—C3	177.6 (5)	C20'—C15'—C14'	116.5 (5)
N3—C5—C6	178.1 (5)	C16'—C15'—C14'	124.4 (4)
C7—C6—C5	117.4 (4)	C17'—C16'—C15'	120.6 (4)
C7—C6—S3	115.7 (4)	C17'—C16'—Br1'	117.7 (4)
C5—C6—S3	126.9 (4)	C15'—C16'—Br1'	121.7 (4)
C6—C7—C8	116.9 (4)	C18'—C17'—C16'	119.8 (5)
C6—C7—S4	117.8 (4)	C18'—C17'—H17'	120.1
C8—C7—S4	125.3 (4)	C16'—C17'—H17'	120.1
N4—C8—C7	177.3 (5)	C17'—C18'—C19'	118.7 (5)
C13—N5—C9	118.3 (4)	C17'—C18'—H18'	120.6
C13—N5—C14	118.0 (4)	C19'—C18'—H18'	120.6
C9—N5—C14	123.6 (4)	C20'—C19'—C18'	122.4 (5)
N5—C9—C10	122.0 (5)	C20'—C19'—H19'	118.8
N5—C9—H9A	119.0	C18'—C19'—H19'	118.8
C10—C9—H9A	119.0	C15'—C20'—C19'	119.4 (5)
C11—C10—C9	118.2 (5)	C15'—C20'—H20'	120.3
C11—C10—H10A	120.9	C19'—C20'—H20'	120.3
C9—C10—H10A	120.9	C2'—S1'—Ni1'	111.47 (16)
C12—C11—C10	120.3 (5)	C3'—S2'—Ni1'	111.07 (16)
C12—C11—H11A	119.9	C6'—S3'—Ni1'	110.40 (16)
C10—C11—H11A	119.9	C7'—S4'—Ni1'	111.56 (16)
C11—C12—C13	120.8 (5)	S2"—Ni1"—S3"	93.82 (5)
C11—C12—H12A	120.4	S2"—Ni1"—S4"	176.36 (5)
C13—C12—H12A	118.8	S3"—Ni1"—S4"	83.64 (5)
N5—C13—C12	120.4 (5)	S2"—Ni1"—S1"	83.61 (5)
N5—C13—H13A	119.8	S3"—Ni1"—S1"	177.05 (5)
C12—C13—H13A	119.8	S4"—Ni1"—S1"	98.98 (5)
C15—C14—N5	119.5 (4)	N1"—C1"—C2"	177.4 (5)
C15—C14—H14A	107.4	C3"—C2"—C1"	119.1 (4)
N5—C14—H14A	107.4	C3"—C2"—S1"	115.4 (4)
C15—C14—H14B	107.4	C1"—C2"—S1"	125.6 (3)
N5—C14—H14B	107.4	C2"—C3"—C4"	116.5 (4)
H14A—C14—H14B	107.0	C2"—C3"—S2"	117.9 (4)
C20—C15—C16	118.9 (4)	C4"—C3"—S2"	125.6 (3)
C20—C15—C14	116.4 (4)	N2"—C4"—C3"	177.7 (5)
C16—C15—C14	124.7 (5)	N3"—C5"—C6"	177.6 (5)
C17—C16—C15	121.2 (4)	C7"—C6"—C5"	118.1 (4)
C17—C16—Br1	117.0 (4)	C7"—C6"—S3"	116.8 (4)
C15—C16—Br1	121.7 (4)	C5"—C6"—S3"	125.0 (4)
C18—C17—C16	119.3 (5)	C6"—C7"—C8"	116.9 (4)
C18—C17—H17A	120.4	C6"—C7"—S4"	117.1 (4)
C16—C17—H17A	120.4	C8"—C7"—S4"	125.9 (4)
C17—C18—C19	118.9 (5)	N4"—C8"—C7"	175.4 (5)
C17—C18—H18A	120.5	C9"—N5"—C13"	118.2 (4)
C19—C18—H18A	120.5	C9"—N5"—C14"	112.9 (4)
C20—C19—C18	122.8 (5)	C13"—N5"—C14"	128.9 (4)
C20—C19—H19A	118.6	N5"—C9"—C10"	120.5 (5)
C18—C19—H19A	118.6	N5"—C9"—H9"	119.7
C19—C20—C15	118.8 (5)	C10"—C9"—H9"	119.7
C19—C20—H20A	120.6	C9"—C10"—C11"	121.0 (6)
C15—C20—H20A	120.6	C9"—C10"—H10"	144.0
C2—S1—Ni1	111.16 (17)	C11"—C10"—H10"	90.8
C3—S2—Ni1	110.82 (16)	C12"—C11"—C10"	119.0 (5)
C6—S3—Ni1	111.49 (16)	C12"—C11"—H11"	120.5
C7—S4—Ni1	111.33 (16)	C10"—C11"—H11"	120.5
S4'—Ni1'—S1'	94.31 (5)	C11"—C12"—C13"	118.7 (5)
S4'—Ni1'—S2'	176.06 (5)	C11"—C12"—H12"	120.7
S1'—Ni1'—S2'	83.69 (5)	C13"—C12"—H12"	120.7
S4'—Ni1'—S3'	83.73 (5)	N5"—C13"—C12"	122.5 (5)
S1'—Ni1'—S3'	176.57 (5)	N5"—C13"—H13"	118.7
S2'—Ni1'—S3'	98.44 (5)	C12"—C13"—H13"	118.7
N1'—C1'—C2'	178.5 (5)	C15"—C14"—N5"	123.5 (4)
C3'—C2'—C1'	117.3 (4)	C15"—C14"—H14E	106.5
C3'—C2'—S1'	117.0 (4)	N5"—C14"—H14E	106.5
C1'—C2'—S1'	125.6 (4)	C15"—C14"—H14F	106.5
C2'—C3'—C4'	117.5 (4)	N5"—C14"—H14F	106.5
C2'—C3'—S2'	116.7 (4)	H14E—C14"—H14F	106.5
C4'—C3'—S2'	125.8 (4)	C20"—C15"—C16"	118.1 (5)
N2'—C4'—C3'	179.4 (6)	C20"—C15"—C14"	116.4 (5)
N3'—C5'—C6'	175.9 (5)	C16"—C15"—C14"	125.4 (5)
C7'—C6'—C5'	118.7 (4)	C17"—C16"—C15"	120.8 (5)
C7'—C6'—S3'	117.2 (4)	C17"—C16"—Br1"	118.5 (4)
C5'—C6'—S3'	124.0 (3)	C15"—C16"—Br1"	120.7 (4)
C6'—C7'—C8'	117.2 (4)	C18"—C17"—C16"	120.1 (5)
C6'—C7'—S4'	117.0 (4)	C18"—C17"—H17"	119.9
C8'—C7'—S4'	125.8 (3)	C16"—C17"—H17"	119.9
N4'—C8'—C7'	178.2 (5)	C17"—C18"—C19"	119.2 (5)
C13'—N5'—C9'	118.6 (4)	C17"—C18"—H18"	120.4
C13'—N5'—C14'	117.2 (4)	C19"—C18"—H18"	120.4
C9'—N5'—C14'	124.2 (4)	C18"—C19"—C20"	121.6 (5)
N5'—C9'—C10'	121.5 (5)	C18"—C19"—H19"	119.2
N5'—C9'—H9'	119.3	C20"—C19"—H19"	119.2
C10'—C9'—H9'	119.3	C15"—C20"—C19"	120.1 (5)
C11'—C10'—C9'	118.8 (5)	C15"—C20"—H20"	119.9
C11'—C10'—H10'	120.6	C19"—C20"—H20"	119.9
C9'—C10'—H10'	120.6	C2"—S1"—Ni1"	111.31 (16)
C12'—C11'—C10'	119.7 (5)	C3"—S2"—Ni1"	111.81 (16)
C12'—C11'—H11'	120.1	C6"—S3"—Ni1"	111.37 (16)
C10'—C11'—H11'	120.1	C7"—S4"—Ni1"	111.03 (16)

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