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The title ionic complex, (C12H12BrN2)2[Ni(C4N2S2)2], crystallizes in a monoclinic unit cell, with the Ni atom on an inversion centre. All bond lengths and angles in the anions and cations are normal. The crystal structure is stabilized by intermol­ecular N—H...S and N—H...N hydrogen bonds, and the weak C—H...N interactions of the anions and cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005343/cv6272sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005343/cv6272Isup2.hkl
Contains datablock I

CCDC reference: 238641

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.051
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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: SAINT (Bruker, 2000); 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.

Bis[1-(3-bromobenzyl)-3-aminopyridinium] bis(maleonitriledithiolato)nickel(II) top
Crystal data top
(C12H12BrN2)2[Ni(C4N2S2)2]F(000) = 1736
Mr = 867.36Dx = 1.685 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 856 reflections
a = 27.219 (7) Åθ = 2.6–23.1°
b = 8.081 (2) ŵ = 3.19 mm1
c = 20.601 (5) ÅT = 293 K
β = 131.01 (1)°Block, red
V = 3419.5 (15) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3011 independent reflections
Radiation source: sealed tube2258 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 3230
Tmin = 0.47, Tmax = 0.53k = 99
16304 measured reflectionsl = 2422
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0913P)2]
where P = (Fo2 + 2Fc2)/3
3011 reflections(Δ/σ)max = 0.001
214 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.65 e Å3
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
xyzUiso*/Ueq
Ni10.25000.25000.50000.0449 (2)
S10.17001 (6)0.37171 (13)0.38150 (8)0.0537 (3)
S20.28594 (5)0.14178 (13)0.44195 (7)0.0536 (3)
N10.0927 (2)0.4027 (5)0.1535 (3)0.0655 (10)
N20.2400 (2)0.1018 (5)0.2291 (3)0.0698 (11)
N30.37722 (15)0.7148 (4)0.5834 (2)0.0450 (8)
N40.30378 (18)0.6064 (5)0.4455 (2)0.0639 (10)
H4A0.28470.55260.45960.077*
H4B0.28980.59870.39420.077*
C10.1310 (2)0.3602 (5)0.2224 (3)0.0529 (10)
C20.17941 (19)0.3053 (5)0.3101 (3)0.0475 (9)
C30.2289 (2)0.2066 (5)0.3364 (3)0.0480 (9)
C40.2357 (2)0.1487 (5)0.2768 (3)0.0530 (10)
C50.35468 (19)0.7010 (5)0.5030 (3)0.0483 (9)
C60.3861 (2)0.7896 (6)0.4811 (3)0.0582 (11)
H6A0.37200.78010.42610.070*
C70.4374 (2)0.8896 (6)0.5401 (3)0.0626 (12)
H7A0.45830.94820.52550.075*
C80.4582 (2)0.9039 (5)0.6211 (3)0.0569 (11)
H8A0.49310.97220.66170.068*
C90.42730 (19)0.8178 (5)0.6412 (3)0.0514 (10)
H9A0.44060.82920.69560.062*
C100.3450 (2)0.6153 (6)0.6076 (3)0.0581 (11)
H10A0.30230.66210.57880.070*
H10B0.33860.50350.58620.070*
C110.38076 (19)0.6068 (5)0.7010 (3)0.0490 (10)
C120.43414 (19)0.5022 (5)0.7533 (3)0.0500 (10)
H12A0.44810.43960.73020.060*
C130.46588 (19)0.4923 (5)0.8389 (3)0.0542 (11)
C140.4453 (2)0.5802 (6)0.8739 (3)0.0646 (12)
H14A0.46690.57100.93210.077*
C150.3921 (3)0.6825 (6)0.8217 (3)0.0691 (13)
H15A0.37770.74300.84490.083*
C160.3606 (2)0.6959 (6)0.7368 (3)0.0586 (11)
H16A0.32480.76610.70230.070*
Br10.54059 (2)0.35526 (6)0.91119 (3)0.0727 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0471 (4)0.0423 (4)0.0594 (5)0.0009 (3)0.0410 (4)0.0017 (3)
S10.0557 (6)0.0555 (7)0.0651 (7)0.0097 (5)0.0461 (6)0.0040 (5)
S20.0517 (6)0.0605 (7)0.0612 (7)0.0089 (5)0.0426 (6)0.0031 (5)
N10.058 (2)0.072 (3)0.064 (3)0.008 (2)0.039 (2)0.002 (2)
N20.066 (3)0.089 (3)0.067 (3)0.012 (2)0.050 (2)0.002 (2)
N30.0377 (16)0.0479 (19)0.0508 (19)0.0024 (14)0.0296 (15)0.0041 (15)
N40.054 (2)0.079 (3)0.049 (2)0.0151 (19)0.0300 (18)0.0031 (18)
C10.053 (3)0.050 (3)0.066 (3)0.002 (2)0.044 (3)0.006 (2)
C20.047 (2)0.046 (2)0.060 (3)0.0011 (18)0.040 (2)0.0006 (19)
C30.049 (2)0.050 (2)0.054 (2)0.0024 (18)0.038 (2)0.0017 (18)
C40.050 (2)0.056 (3)0.059 (3)0.0009 (19)0.039 (2)0.002 (2)
C50.042 (2)0.051 (2)0.053 (2)0.0024 (18)0.032 (2)0.0061 (19)
C60.057 (3)0.063 (3)0.063 (3)0.000 (2)0.043 (2)0.009 (2)
C70.059 (3)0.058 (3)0.082 (3)0.002 (2)0.051 (3)0.014 (2)
C80.046 (2)0.048 (2)0.073 (3)0.0063 (19)0.038 (2)0.001 (2)
C90.045 (2)0.048 (2)0.060 (3)0.0046 (18)0.034 (2)0.000 (2)
C100.047 (2)0.071 (3)0.058 (3)0.015 (2)0.036 (2)0.001 (2)
C110.044 (2)0.054 (2)0.054 (2)0.0111 (19)0.033 (2)0.0019 (19)
C120.048 (2)0.048 (2)0.062 (3)0.0045 (19)0.039 (2)0.002 (2)
C130.054 (2)0.049 (3)0.061 (3)0.0019 (19)0.038 (2)0.007 (2)
C140.077 (3)0.068 (3)0.058 (3)0.005 (3)0.048 (3)0.011 (2)
C150.079 (3)0.073 (3)0.074 (3)0.012 (3)0.058 (3)0.005 (3)
C160.060 (3)0.058 (3)0.067 (3)0.009 (2)0.045 (2)0.012 (2)
Br10.0621 (3)0.0595 (4)0.0821 (4)0.0092 (2)0.0411 (3)0.0175 (2)
Geometric parameters (Å, º) top
Ni1—S22.1649 (11)C7—C81.372 (7)
Ni1—S2i2.1649 (11)C7—H7A0.9300
Ni1—S1i2.1662 (12)C8—C91.348 (6)
Ni1—S12.1662 (12)C8—H8A0.9300
S1—C21.735 (4)C9—H9A0.9300
S2—C31.727 (4)C10—C111.482 (6)
N1—C11.131 (6)C10—H10A0.9700
N2—C41.129 (5)C10—H10B0.9700
N3—C51.341 (5)C11—C161.378 (6)
N3—C91.356 (5)C11—C121.390 (6)
N3—C101.497 (5)C12—C131.366 (6)
N4—C51.324 (6)C12—H12A0.9300
N4—H4A0.8600C13—C141.367 (6)
N4—H4B0.8600C13—Br11.899 (4)
C1—C21.440 (7)C14—C151.375 (7)
C2—C31.336 (6)C14—H14A0.9300
C3—C41.436 (6)C15—C161.356 (7)
C5—C61.399 (6)C15—H15A0.9300
C6—C71.360 (7)C16—H16A0.9300
C6—H6A0.9300
S2—Ni1—S2i180.00 (4)C9—C8—C7119.1 (4)
S2—Ni1—S1i87.41 (5)C9—C8—H8A120.4
S2i—Ni1—S1i92.59 (5)C7—C8—H8A120.4
S2—Ni1—S192.59 (5)C8—C9—N3121.2 (4)
S2i—Ni1—S187.41 (5)C8—C9—H9A119.4
S1i—Ni1—S1180.00 (7)N3—C9—H9A119.4
C2—S1—Ni1102.51 (15)C11—C10—N3115.4 (3)
C3—S2—Ni1102.33 (14)C11—C10—H10A108.4
C5—N3—C9121.1 (3)N3—C10—H10A108.4
C5—N3—C10118.3 (3)C11—C10—H10B108.4
C9—N3—C10120.6 (4)N3—C10—H10B108.4
C5—N4—H4A120.0H10A—C10—H10B107.5
C5—N4—H4B120.0C16—C11—C12119.0 (4)
H4A—N4—H4B120.0C16—C11—C10121.2 (4)
N1—C1—C2179.6 (5)C12—C11—C10119.8 (4)
C3—C2—C1122.8 (4)C13—C12—C11119.3 (4)
C3—C2—S1120.7 (3)C13—C12—H12A120.3
C1—C2—S1116.4 (3)C11—C12—H12A120.3
C2—C3—C4120.6 (4)C12—C13—C14121.3 (4)
C2—C3—S2121.7 (3)C12—C13—Br1119.4 (3)
C4—C3—S2117.6 (3)C14—C13—Br1119.2 (3)
N2—C4—C3178.7 (5)C13—C14—C15119.0 (4)
N4—C5—N3120.9 (4)C13—C14—H14A120.5
N4—C5—C6120.7 (4)C15—C14—H14A120.5
N3—C5—C6118.4 (4)C16—C15—C14120.5 (4)
C7—C6—C5120.0 (4)C16—C15—H15A119.7
C7—C6—H6A120.0C14—C15—H15A119.7
C5—C6—H6A120.0C15—C16—C11120.8 (4)
C6—C7—C8120.0 (4)C15—C16—H16A119.6
C6—C7—H7A120.0C11—C16—H16A119.6
C8—C7—H7A120.0
Symmetry code: (i) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···S10.862.813.506 (4)140
N4—H4B···N2ii0.862.102.956 (6)175
C6—H6A···N1ii0.932.583.308 (6)136
Symmetry code: (ii) x+1/2, y+1/2, z+1/2.
 

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