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The title compound, (C12H12BrN2)[Ni(C4N2S2)2], is an ion-pair complex, isostructural with the Cl-containing analogue. The anion lies on an inversion centre and the NiII ion is coordinated by four S atoms, giving the expected square-planar coordination geometry. The cation adopts a conformation where the benzene and pyrazine rings are twisted with respect to the plane of the central C—C—N chain which links them. C—H...S and π–π inter­actions between cations and anions are observed in the crystal structure, and C—H...π inter­actions mediate the formation of ribbons of cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008373/bh2003sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008373/bh2003Isup2.hkl
Contains datablock I

CCDC reference: 604965

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.117
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.42 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.46 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis[1-(4-bromobenzyl)-3-methylpyrazinium] bis(1,2-dicyanoethene-1,2-dithiolato-κ3S,S')nickelate(II) top
Crystal data top
(C12H12BrN2)2[Ni(C4N2S2)2]F(000) = 868
Mr = 867.36Dx = 1.641 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 908 reflections
a = 7.182 (2) Åθ = 2.9–23.6°
b = 15.944 (4) ŵ = 3.10 mm1
c = 15.384 (4) ÅT = 293 K
β = 94.692 (10)°Block, red
V = 1755.7 (8) Å30.25 × 0.20 × 0.15 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3085 independent reflections
Radiation source: sealed tube2162 reflections with I > 2σ(I)
Graphite' monochromatorRint = 0.097
φ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 88
Tmin = 0.480, Tmax = 0.628k = 1618
8550 measured reflectionsl = 1718
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0649P)2]
where P = (Fo2 + 2Fc2)/3
3085 reflections(Δ/σ)max = 0.032
215 parametersΔρmax = 0.84 e Å3
0 restraintsΔρmin = 0.82 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
Ni10.00000.50000.00000.0406 (2)
S10.14451 (15)0.41032 (6)0.07610 (7)0.0509 (3)
S20.25519 (15)0.50956 (6)0.08510 (7)0.0550 (3)
N10.0389 (8)0.2542 (3)0.2512 (3)0.0980 (16)
N20.4563 (8)0.6344 (3)0.2724 (3)0.1075 (18)
Br10.14550 (7)0.08035 (4)0.02801 (4)0.0853 (2)
C20.0105 (7)0.3100 (3)0.2089 (3)0.0610 (12)
C10.0283 (6)0.3780 (2)0.1533 (2)0.0477 (10)
C40.3445 (8)0.6136 (3)0.2216 (3)0.0674 (13)
C30.2009 (6)0.5865 (2)0.1574 (3)0.0511 (10)
C50.7388 (6)0.3799 (3)0.1473 (3)0.0570 (11)
H50.62960.37690.11050.068*
C60.7544 (7)0.4357 (3)0.2145 (3)0.0631 (12)
H60.65330.47060.22210.076*
C71.0480 (7)0.3937 (3)0.2553 (3)0.0544 (11)
C81.0379 (6)0.3373 (2)0.1877 (3)0.0542 (10)
H81.14090.30410.17850.065*
C90.8800 (6)0.2701 (3)0.0595 (3)0.0618 (12)
H9A0.91060.30090.00820.074*
H9B0.97660.22830.07200.074*
C100.6972 (6)0.2261 (2)0.0392 (2)0.0461 (9)
C110.5613 (7)0.2574 (3)0.0204 (3)0.0667 (13)
H110.58040.30860.04740.080*
C120.3980 (6)0.2143 (3)0.0407 (3)0.0679 (13)
H120.30690.23590.08100.081*
C130.3713 (6)0.1396 (3)0.0011 (3)0.0534 (10)
C140.5055 (6)0.1064 (2)0.0579 (3)0.0537 (10)
H140.48570.05500.08430.064*
C150.6691 (6)0.1495 (2)0.0777 (2)0.0502 (10)
H150.76090.12710.11700.060*
C161.2231 (8)0.4018 (3)0.3144 (3)0.0795 (15)
H16A1.25680.45990.32030.119*
H16B1.32200.37150.29010.119*
H16C1.20270.37920.37060.119*
N30.8821 (5)0.32974 (19)0.13510 (19)0.0473 (8)
N40.9049 (6)0.4432 (2)0.2696 (2)0.0621 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0459 (4)0.0344 (4)0.0402 (4)0.0001 (3)0.0049 (3)0.0010 (3)
S10.0521 (7)0.0464 (6)0.0534 (6)0.0040 (5)0.0006 (5)0.0068 (4)
S20.0531 (7)0.0539 (6)0.0550 (6)0.0058 (5)0.0126 (5)0.0088 (5)
N10.150 (5)0.066 (3)0.082 (3)0.005 (3)0.037 (3)0.024 (2)
N20.120 (4)0.094 (4)0.098 (4)0.001 (3)0.057 (3)0.028 (3)
Br10.0474 (3)0.0896 (4)0.1168 (5)0.0135 (3)0.0068 (3)0.0258 (3)
C20.090 (4)0.047 (2)0.046 (2)0.003 (2)0.010 (2)0.001 (2)
C10.066 (3)0.040 (2)0.037 (2)0.005 (2)0.0000 (18)0.0049 (16)
C40.084 (4)0.057 (3)0.057 (3)0.005 (3)0.019 (3)0.010 (2)
C30.064 (3)0.044 (2)0.044 (2)0.008 (2)0.0088 (19)0.0011 (17)
C50.050 (3)0.053 (3)0.067 (3)0.006 (2)0.003 (2)0.000 (2)
C60.059 (3)0.056 (3)0.075 (3)0.000 (2)0.007 (2)0.004 (2)
C70.063 (3)0.048 (2)0.050 (3)0.007 (2)0.004 (2)0.003 (2)
C80.053 (3)0.047 (2)0.062 (3)0.002 (2)0.002 (2)0.003 (2)
C90.062 (3)0.063 (3)0.061 (3)0.022 (2)0.014 (2)0.015 (2)
C100.051 (3)0.045 (2)0.042 (2)0.0065 (19)0.0000 (18)0.0043 (17)
C110.088 (4)0.048 (3)0.062 (3)0.009 (2)0.013 (2)0.013 (2)
C120.065 (3)0.052 (3)0.081 (3)0.008 (2)0.028 (2)0.003 (2)
C130.043 (2)0.052 (3)0.064 (3)0.0024 (19)0.0054 (19)0.010 (2)
C140.061 (3)0.044 (2)0.055 (3)0.010 (2)0.002 (2)0.0058 (18)
C150.051 (3)0.048 (2)0.050 (2)0.0014 (19)0.0096 (18)0.0043 (18)
C160.081 (4)0.085 (4)0.069 (3)0.001 (3)0.017 (3)0.009 (3)
N30.050 (2)0.0430 (18)0.0490 (19)0.0125 (16)0.0031 (16)0.0017 (15)
N40.071 (3)0.055 (2)0.060 (2)0.003 (2)0.005 (2)0.0077 (17)
Geometric parameters (Å, º) top
Ni1—S1i2.1659 (10)C7—C161.495 (6)
Ni1—S12.1659 (10)C8—N31.332 (5)
Ni1—S2i2.1687 (11)C8—H80.9300
Ni1—S22.1687 (11)C9—C101.498 (5)
S1—C11.724 (4)C9—N31.502 (5)
S2—C31.722 (4)C9—H9A0.9700
N1—C21.131 (5)C9—H9B0.9700
N2—C41.124 (6)C10—C151.378 (5)
Br1—C131.893 (4)C10—C111.378 (6)
C2—C11.423 (6)C11—C121.373 (6)
C1—C3i1.360 (6)C11—H110.9300
C4—C31.435 (6)C12—C131.359 (6)
C3—C1i1.360 (6)C12—H120.9300
C5—N31.328 (5)C13—C141.374 (6)
C5—C61.362 (6)C14—C151.374 (5)
C5—H50.9300C14—H140.9300
C6—N41.324 (6)C15—H150.9300
C6—H60.9300C16—H16A0.9600
C7—N41.328 (6)C16—H16B0.9600
C7—C81.373 (6)C16—H16C0.9600
S1i—Ni1—S1180.00 (5)C10—C9—H9B108.7
S1i—Ni1—S2i87.36 (4)N3—C9—H9B108.7
S1—Ni1—S2i92.64 (4)H9A—C9—H9B107.6
S1i—Ni1—S292.64 (4)C15—C10—C11119.1 (4)
S1—Ni1—S287.36 (4)C15—C10—C9118.8 (4)
S2i—Ni1—S2180.00 (5)C11—C10—C9122.0 (4)
C1—S1—Ni1102.68 (15)C12—C11—C10121.0 (4)
C3—S2—Ni1102.43 (15)C12—C11—H11119.5
N1—C2—C1177.7 (5)C10—C11—H11119.5
C3i—C1—C2120.8 (4)C13—C12—C11119.1 (4)
C3i—C1—S1120.7 (3)C13—C12—H12120.4
C2—C1—S1118.4 (3)C11—C12—H12120.4
N2—C4—C3179.4 (7)C12—C13—C14121.1 (4)
C1i—C3—C4120.5 (4)C12—C13—Br1119.2 (3)
C1i—C3—S2121.3 (3)C14—C13—Br1119.6 (3)
C4—C3—S2118.1 (4)C13—C14—C15119.6 (4)
N3—C5—C6118.9 (4)C13—C14—H14120.2
N3—C5—H5120.5C15—C14—H14120.2
C6—C5—H5120.5C14—C15—C10120.1 (4)
N4—C6—C5123.9 (5)C14—C15—H15120.0
N4—C6—H6118.0C10—C15—H15120.0
C5—C6—H6118.0C7—C16—H16A109.5
N4—C7—C8121.4 (4)C7—C16—H16B109.5
N4—C7—C16118.2 (4)H16A—C16—H16B109.5
C8—C7—C16120.4 (4)C7—C16—H16C109.5
N3—C8—C7120.6 (4)H16A—C16—H16C109.5
N3—C8—H8119.7H16B—C16—H16C109.5
C7—C8—H8119.7C5—N3—C8118.8 (4)
C10—C9—N3114.3 (3)C5—N3—C9122.1 (4)
C10—C9—H9A108.7C8—N3—C9118.8 (4)
N3—C9—H9A108.7C6—N4—C7116.2 (4)
Symmetry code: (i) x, y+1, z.
 

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