Download citation
Download citation
link to html
In the title compound, (C13H13BrN)[Ni(C6H4S2)2], the NiIII atom is surrounded by four S atoms in a square-planar geometry. The asymmetric unit contains half each of two centrosymmetric anions and a single cation in a general position. The anions exhibit two packing modes, viz. stacked in a face-to-face fashion with an alternate arrangement of anions and cations, and stacked in a side-by-side fashion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025931/hk2072sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025931/hk2072Isup2.hkl
Contains datablock I

CCDC reference: 618232

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.058
  • wR factor = 0.159
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-(4-Bromobenzylmethyl)pyridinium bis(benzene-1,2-dithiolato)nickelate(III) top
Crystal data top
(C13H13BrN)[Ni(C6H4S2)2]Z = 2
Mr = 602.29F(000) = 610
Triclinic, P1Dx = 1.611 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2661 (11) ÅCell parameters from 1623 reflections
b = 12.4666 (19) Åθ = 2.5–22.2°
c = 14.255 (2) ŵ = 2.74 mm1
α = 76.446 (3)°T = 294 K
β = 82.992 (3)°Prism, dark green
γ = 83.819 (3)°0.30 × 0.10 × 0.10 mm
V = 1241.7 (3) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4282 independent reflections
Radiation source: fine-focus sealed tube3257 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 88
Tmin = 0.489, Tmax = 0.764k = 1114
6105 measured reflectionsl = 1616
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0575P)2 + 0.6467P]
where P = (Fo2 + 2Fc2)/3
4282 reflections(Δ/σ)max < 0.001
293 parametersΔρmax = 1.33 e Å3
0 restraintsΔρmin = 0.94 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50001.00000.00000.0505 (3)
Ni20.50000.00000.50000.0532 (3)
S10.51763 (19)0.02698 (11)0.64217 (9)0.0568 (4)
S20.4490 (2)0.17402 (12)0.44098 (9)0.0636 (4)
S30.77346 (18)0.92470 (11)0.02538 (10)0.0573 (4)
S40.39580 (19)0.84263 (12)0.00997 (11)0.0618 (4)
Br10.28122 (16)0.48203 (6)0.25601 (6)0.1222 (4)
N10.0316 (6)0.0223 (4)0.2701 (3)0.0580 (11)
C10.4290 (7)0.2341 (4)0.5407 (3)0.0514 (12)
C20.3802 (8)0.3483 (5)0.5311 (4)0.0631 (14)
H20.36130.39320.47040.076*
C30.3605 (9)0.3934 (5)0.6114 (5)0.0718 (16)
H30.32800.46880.60530.086*
C40.3896 (8)0.3255 (5)0.7021 (4)0.0701 (16)
H40.37580.35590.75640.084*
C50.4380 (7)0.2152 (5)0.7119 (4)0.0598 (13)
H50.45860.17130.77270.072*
C60.4570 (7)0.1672 (4)0.6315 (4)0.0532 (12)
C70.5859 (7)0.7463 (4)0.0326 (4)0.0543 (12)
C80.5726 (9)0.6340 (5)0.0445 (4)0.0661 (15)
H80.45850.60850.04110.079*
C90.7249 (10)0.5597 (5)0.0613 (4)0.0730 (16)
H90.71420.48450.06850.088*
C100.8927 (9)0.5969 (5)0.0672 (4)0.0714 (16)
H100.99560.54630.07890.086*
C110.9117 (8)0.7075 (5)0.0563 (4)0.0657 (15)
H111.02680.73150.06020.079*
C120.7570 (7)0.7839 (4)0.0394 (3)0.0531 (12)
C130.1644 (11)0.3587 (5)0.2425 (4)0.0723 (17)
C140.0232 (13)0.3572 (6)0.2623 (5)0.094 (2)
H140.09280.41660.28200.112*
C150.1110 (9)0.2669 (6)0.2533 (5)0.084 (2)
H150.23890.26480.26840.100*
C160.0064 (8)0.1803 (4)0.2215 (4)0.0583 (13)
C170.1817 (8)0.1860 (5)0.2015 (4)0.0614 (14)
H170.25290.12780.18070.074*
C180.2696 (8)0.2754 (5)0.2110 (4)0.0638 (14)
H180.39750.27810.19620.077*
C190.0963 (9)0.0841 (5)0.2064 (5)0.0707 (16)
H19A0.23020.09660.21910.085*
H19B0.06880.07900.13910.085*
C200.0527 (8)0.0333 (5)0.3662 (4)0.0646 (14)
H200.10150.02670.39230.078*
C210.0036 (8)0.1315 (5)0.4262 (4)0.0690 (15)
H210.01710.13800.49300.083*
C220.0665 (7)0.2219 (5)0.3883 (5)0.0655 (15)
C230.0879 (9)0.2067 (6)0.2901 (5)0.0798 (18)
H230.13670.26530.26220.096*
C240.0393 (9)0.1077 (5)0.2326 (5)0.0730 (16)
H240.05570.09910.16560.088*
C250.1158 (10)0.3327 (6)0.4537 (6)0.094 (2)
H25A0.01400.37840.46250.140*
H25B0.14000.32200.51550.140*
H25C0.22470.36810.42480.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0480 (5)0.0560 (5)0.0494 (5)0.0133 (4)0.0078 (4)0.0101 (4)
Ni20.0553 (6)0.0614 (6)0.0392 (5)0.0011 (4)0.0018 (4)0.0070 (4)
S10.0606 (8)0.0641 (8)0.0423 (7)0.0011 (6)0.0076 (6)0.0059 (6)
S20.0807 (10)0.0652 (8)0.0404 (7)0.0017 (7)0.0044 (6)0.0053 (6)
S30.0492 (7)0.0613 (8)0.0646 (8)0.0134 (6)0.0112 (6)0.0137 (6)
S40.0524 (8)0.0625 (8)0.0743 (9)0.0163 (6)0.0137 (7)0.0139 (7)
Br10.2086 (11)0.0710 (5)0.0948 (6)0.0456 (6)0.0377 (6)0.0073 (4)
N10.053 (3)0.064 (3)0.057 (3)0.015 (2)0.015 (2)0.005 (2)
C10.045 (3)0.063 (3)0.045 (3)0.007 (2)0.002 (2)0.009 (2)
C20.062 (3)0.066 (4)0.059 (3)0.004 (3)0.011 (3)0.008 (3)
C30.077 (4)0.061 (3)0.079 (4)0.004 (3)0.009 (3)0.017 (3)
C40.075 (4)0.077 (4)0.064 (4)0.011 (3)0.003 (3)0.027 (3)
C50.054 (3)0.074 (4)0.049 (3)0.008 (3)0.006 (2)0.009 (3)
C60.044 (3)0.063 (3)0.053 (3)0.006 (2)0.002 (2)0.013 (2)
C70.058 (3)0.063 (3)0.046 (3)0.016 (2)0.005 (2)0.014 (2)
C80.079 (4)0.066 (4)0.058 (3)0.017 (3)0.008 (3)0.017 (3)
C90.094 (5)0.060 (3)0.069 (4)0.006 (3)0.012 (3)0.021 (3)
C100.076 (4)0.067 (4)0.073 (4)0.003 (3)0.005 (3)0.025 (3)
C110.056 (3)0.079 (4)0.062 (3)0.004 (3)0.003 (3)0.018 (3)
C120.059 (3)0.057 (3)0.043 (3)0.010 (2)0.001 (2)0.011 (2)
C130.110 (5)0.060 (4)0.046 (3)0.019 (3)0.011 (3)0.003 (3)
C140.132 (7)0.062 (4)0.075 (4)0.005 (4)0.013 (4)0.006 (3)
C150.069 (4)0.078 (4)0.088 (5)0.001 (3)0.014 (3)0.002 (4)
C160.057 (3)0.062 (3)0.048 (3)0.005 (3)0.009 (2)0.004 (2)
C170.070 (4)0.064 (3)0.051 (3)0.002 (3)0.016 (3)0.010 (3)
C180.069 (4)0.073 (4)0.049 (3)0.016 (3)0.011 (3)0.007 (3)
C190.066 (4)0.069 (4)0.071 (4)0.013 (3)0.017 (3)0.004 (3)
C200.071 (4)0.071 (4)0.054 (3)0.013 (3)0.006 (3)0.015 (3)
C210.067 (4)0.083 (4)0.056 (3)0.018 (3)0.011 (3)0.005 (3)
C220.044 (3)0.071 (4)0.079 (4)0.010 (3)0.017 (3)0.004 (3)
C230.071 (4)0.081 (5)0.088 (5)0.006 (3)0.009 (3)0.024 (4)
C240.076 (4)0.079 (4)0.069 (4)0.006 (3)0.013 (3)0.022 (3)
C250.078 (5)0.080 (4)0.113 (6)0.006 (4)0.031 (4)0.008 (4)
Geometric parameters (Å, º) top
Ni1—S3i2.1389 (14)C9—H90.9300
Ni1—S32.1389 (14)C10—C111.370 (8)
Ni1—S42.1460 (13)C10—H100.9300
Ni1—S4i2.1461 (13)C11—C121.399 (8)
Ni2—S22.1445 (14)C11—H110.9300
Ni2—S2ii2.1445 (14)C13—C181.352 (8)
Ni2—S1ii2.1514 (13)C13—C141.359 (10)
Ni2—S12.1515 (13)C14—C151.390 (10)
S1—C61.732 (5)C14—H140.9300
S2—C11.740 (5)C15—C161.385 (8)
S3—C121.735 (5)C15—H150.9300
S4—C71.738 (6)C16—C171.368 (7)
Br1—C131.892 (6)C16—C191.495 (8)
N1—C241.329 (7)C17—C181.384 (8)
N1—C201.336 (7)C17—H170.9300
N1—C191.486 (7)C18—H180.9300
C1—C61.390 (7)C19—H19A0.9700
C1—C21.409 (7)C19—H19B0.9700
C2—C31.375 (8)C20—C211.359 (8)
C2—H20.9300C20—H200.9300
C3—C41.396 (8)C21—C221.384 (8)
C3—H30.9300C21—H210.9300
C4—C51.361 (8)C22—C231.359 (9)
C4—H40.9300C22—C251.509 (8)
C5—C61.399 (7)C23—C241.350 (9)
C5—H50.9300C23—H230.9300
C7—C81.383 (7)C24—H240.9300
C7—C121.397 (7)C25—H25A0.9600
C8—C91.371 (9)C25—H25B0.9600
C8—H80.9300C25—H25C0.9600
C9—C101.369 (8)
S3i—Ni1—S3180.0C10—C11—H11120.2
S3i—Ni1—S488.12 (5)C12—C11—H11120.2
S3—Ni1—S491.88 (5)C7—C12—C11119.4 (5)
S3i—Ni1—S4i91.88 (5)C7—C12—S3119.2 (4)
S3—Ni1—S4i88.12 (5)C11—C12—S3121.4 (4)
S4—Ni1—S4i180.00 (8)C18—C13—C14121.7 (6)
S2—Ni2—S2ii180.0C18—C13—Br1118.9 (5)
S2—Ni2—S1ii88.17 (5)C14—C13—Br1119.3 (5)
S2ii—Ni2—S1ii91.82 (5)C13—C14—C15120.0 (6)
S2—Ni2—S191.82 (5)C13—C14—H14120.0
S2ii—Ni2—S188.18 (5)C15—C14—H14120.0
S1ii—Ni2—S1179.999 (1)C16—C15—C14119.5 (6)
C6—S1—Ni2104.57 (18)C16—C15—H15120.3
C1—S2—Ni2104.66 (18)C14—C15—H15120.3
C12—S3—Ni1105.15 (19)C17—C16—C15118.4 (6)
C7—S4—Ni1105.03 (17)C17—C16—C19120.4 (5)
C24—N1—C20119.9 (5)C15—C16—C19121.2 (5)
C24—N1—C19120.6 (5)C16—C17—C18122.3 (5)
C20—N1—C19119.4 (5)C16—C17—H17118.8
C6—C1—C2119.8 (5)C18—C17—H17118.8
C6—C1—S2119.1 (4)C13—C18—C17118.1 (6)
C2—C1—S2121.0 (4)C13—C18—H18120.9
C3—C2—C1120.0 (5)C17—C18—H18120.9
C3—C2—H2120.0N1—C19—C16112.4 (5)
C1—C2—H2120.0N1—C19—H19A109.1
C2—C3—C4119.7 (6)C16—C19—H19A109.1
C2—C3—H3120.2N1—C19—H19B109.1
C4—C3—H3120.2C16—C19—H19B109.1
C5—C4—C3120.8 (5)H19A—C19—H19B107.9
C5—C4—H4119.6N1—C20—C21120.5 (6)
C3—C4—H4119.6N1—C20—H20119.7
C4—C5—C6120.6 (5)C21—C20—H20119.7
C4—C5—H5119.7C20—C21—C22120.2 (6)
C6—C5—H5119.7C20—C21—H21119.9
C1—C6—C5119.1 (5)C22—C21—H21119.9
C1—C6—S1119.3 (4)C23—C22—C21117.3 (6)
C5—C6—S1121.5 (4)C23—C22—C25121.7 (6)
C8—C7—C12119.1 (5)C21—C22—C25121.1 (6)
C8—C7—S4122.1 (4)C24—C23—C22121.0 (6)
C12—C7—S4118.8 (4)C24—C23—H23119.5
C9—C8—C7121.1 (6)C22—C23—H23119.5
C9—C8—H8119.5N1—C24—C23121.1 (6)
C7—C8—H8119.5N1—C24—H24119.5
C10—C9—C8119.6 (6)C23—C24—H24119.5
C10—C9—H9120.2C22—C25—H25A109.5
C8—C9—H9120.2C22—C25—H25B109.5
C9—C10—C11121.2 (6)H25A—C25—H25B109.5
C9—C10—H10119.4C22—C25—H25C109.5
C11—C10—H10119.4H25A—C25—H25C109.5
C10—C11—C12119.6 (6)H25B—C25—H25C109.5
S2—Ni2—S1—C66.26 (18)S4—C7—C12—C11179.2 (4)
S2ii—Ni2—S1—C6173.74 (18)C8—C7—C12—S3179.5 (4)
S1ii—Ni2—S2—C1174.51 (18)S4—C7—C12—S30.1 (6)
S1—Ni2—S2—C15.49 (18)C10—C11—C12—C70.9 (8)
S4—Ni1—S3—C120.11 (17)C10—C11—C12—S3179.9 (4)
S4i—Ni1—S3—C12179.89 (17)Ni1—S3—C12—C70.0 (4)
S3i—Ni1—S4—C7179.83 (18)Ni1—S3—C12—C11179.3 (4)
S3—Ni1—S4—C70.17 (18)C18—C13—C14—C152.0 (10)
Ni2—S2—C1—C63.3 (4)Br1—C13—C14—C15179.6 (5)
Ni2—S2—C1—C2175.0 (4)C13—C14—C15—C161.7 (10)
C6—C1—C2—C30.0 (8)C14—C15—C16—C171.0 (9)
S2—C1—C2—C3178.3 (4)C14—C15—C16—C19177.1 (6)
C1—C2—C3—C40.2 (9)C15—C16—C17—C180.6 (8)
C2—C3—C4—C50.3 (9)C19—C16—C17—C18177.5 (5)
C3—C4—C5—C60.9 (9)C14—C13—C18—C171.5 (9)
C2—C1—C6—C50.7 (7)Br1—C13—C18—C17179.9 (4)
S2—C1—C6—C5179.0 (4)C16—C17—C18—C130.8 (8)
C2—C1—C6—S1179.8 (4)C24—N1—C19—C16125.2 (6)
S2—C1—C6—S11.9 (6)C20—N1—C19—C1657.7 (7)
C4—C5—C6—C11.1 (8)C17—C16—C19—N163.4 (7)
C4—C5—C6—S1179.8 (4)C15—C16—C19—N1118.6 (6)
Ni2—S1—C6—C16.0 (4)C24—N1—C20—C210.5 (8)
Ni2—S1—C6—C5174.9 (4)C19—N1—C20—C21176.6 (5)
Ni1—S4—C7—C8179.5 (4)N1—C20—C21—C221.0 (9)
Ni1—S4—C7—C120.2 (4)C20—C21—C22—C231.8 (8)
C12—C7—C8—C91.0 (8)C20—C21—C22—C25177.9 (5)
S4—C7—C8—C9179.3 (4)C21—C22—C23—C241.1 (9)
C7—C8—C9—C100.6 (9)C25—C22—C23—C24178.5 (6)
C8—C9—C10—C110.3 (9)C20—N1—C24—C231.2 (9)
C9—C10—C11—C120.4 (9)C19—N1—C24—C23175.9 (6)
C8—C7—C12—C111.2 (7)C22—C23—C24—N10.3 (10)
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds