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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m972.
Published online 2009 July 22. doi:  10.1107/S1600536809028128
PMCID: PMC2977401

Bis[4-(dimethyl­amino)pyridinium] tetra­bromidocuprate(II)

Abstract

The metal atom in the anion of the title salt, (C7H11N2)2[CuBr4], shows a distorted tetra­hedral coordination. The primary contacts between the ions are of the N—H(...)Br type.

Related literature

For other pyridinium tetra­bromidocuprates, see: Coffey et al. (1996 [triangle]); Haddad & Al-Far (2008 [triangle]); Luque et al. (2001 [triangle]); Willet et al. (2000 [triangle], 2003 [triangle]).

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Object name is e-65-0m972-scheme1.jpg

Experimental

Crystal data

  • (C7H11N2)2[CuBr4]
  • M r = 629.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m972-efi1.jpg
  • a = 8.1768 (2) Å
  • b = 9.2406 (3) Å
  • c = 14.3686 (4) Å
  • α = 93.689 (2)°
  • β = 94.814 (2)°
  • γ = 105.073 (2)°
  • V = 1040.42 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 8.73 mm−1
  • T = 233 K
  • 0.35 × 0.30 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.321, T max = 0.746 (expected range = 0.180–0.418)
  • 7224 measured reflections
  • 4595 independent reflections
  • 3168 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.123
  • S = 1.00
  • 4595 reflections
  • 213 parameters
  • H-atom parameters constrained
  • Δρmax = 0.84 e Å−3
  • Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028128/tk2503sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028128/tk2503Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya (RG020/09AFR) for supporting this study.

supplementary crystallographic information

Experimental

Copper sulfate pentahydrate (2.1 g, 8.3 mmol) dissolved in water (5 ml) was mixed with 4-dimethylaminopyridine hydrobromide perbromide (3 g, 8.3 mmol) dissolved in ethanol (10 ml). The mixture was heated for 30 min. The filtered green solution when allowed to evaporate yielded black crystals.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.94–0.97 Å; N–H 0.88 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5Ueq(C, N).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of 2[C7H11N2][CuBr4] at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(C7H11N2)2[CuBr4]Z = 2
Mr = 629.54F(000) = 606
Triclinic, P1Dx = 2.010 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1768 (2) ÅCell parameters from 2442 reflections
b = 9.2406 (3) Åθ = 2.3–27.5°
c = 14.3686 (4) ŵ = 8.73 mm1
α = 93.689 (2)°T = 233 K
β = 94.814 (2)°Block, black
γ = 105.073 (2)°0.35 × 0.30 × 0.10 mm
V = 1040.42 (5) Å3

Data collection

Bruker SMART APEX diffractometer4595 independent reflections
Radiation source: fine-focus sealed tube3168 reflections with I > 2σ(I)
graphiteRint = 0.042
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.321, Tmax = 0.746k = −10→12
7224 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.123w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4595 reflectionsΔρmax = 0.84 e Å3
213 parametersΔρmin = −0.82 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0078 (8)

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

xyzUiso*/Ueq
Br10.46757 (8)0.23274 (7)0.31534 (5)0.04383 (19)
Br20.44673 (8)0.69937 (7)0.29470 (5)0.0458 (2)
Br30.11950 (8)0.35808 (7)0.20247 (4)0.03895 (18)
Br40.65667 (8)0.48740 (7)0.15029 (4)0.04107 (19)
Cu10.41731 (9)0.44301 (7)0.23676 (5)0.0323 (2)
N10.8043 (9)0.5220 (8)0.4011 (5)0.067 (2)
H10.73350.44340.36850.081*
N21.1304 (7)0.8919 (6)0.5502 (4)0.0466 (13)
N30.6251 (7)0.8455 (6)0.1004 (4)0.0478 (13)
H30.57940.77760.13760.057*
N40.8436 (7)1.1604 (6)−0.0731 (3)0.0415 (12)
C10.9472 (12)0.5930 (9)0.3673 (5)0.063 (2)
H1A0.97090.55760.30850.075*
C21.0582 (9)0.7127 (9)0.4141 (5)0.0521 (18)
H21.15890.75960.38870.062*
C31.0231 (7)0.7695 (7)0.5032 (4)0.0343 (13)
C40.8711 (8)0.6903 (8)0.5360 (5)0.0465 (16)
H40.84090.72130.59420.056*
C50.7692 (9)0.5702 (9)0.4836 (5)0.064 (2)
H50.66830.51790.50670.077*
C61.2928 (10)0.9673 (9)0.5180 (6)0.067 (2)
H6A1.27231.01010.45970.100*
H6B1.35850.89510.50800.100*
H6C1.35561.04690.56500.100*
C71.0967 (10)0.9465 (9)0.6426 (5)0.062 (2)
H7A0.98140.95710.63930.093*
H7B1.17671.04330.66230.093*
H7C1.10950.87520.68750.093*
C80.6803 (9)0.8036 (7)0.0201 (5)0.0472 (17)
H80.66880.70080.00450.057*
C90.7497 (8)0.9012 (7)−0.0374 (4)0.0409 (15)
H90.78580.8671−0.09310.049*
C100.7710 (7)1.0591 (6)−0.0161 (4)0.0328 (13)
C110.7118 (7)1.1009 (7)0.0682 (4)0.0374 (14)
H110.72171.20260.08630.045*
C120.6401 (8)0.9918 (8)0.1234 (4)0.0462 (17)
H120.59991.02000.17930.055*
C130.9027 (9)1.1174 (9)−0.1615 (5)0.0558 (18)
H13A0.94151.0274−0.15530.084*
H13B0.99601.1986−0.17640.084*
H13C0.80991.0977−0.21120.084*
C140.8708 (10)1.3216 (6)−0.0511 (5)0.059 (2)
H14A0.95131.35510.00440.088*
H14B0.76351.3424−0.03980.088*
H14C0.91581.3747−0.10350.088*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0494 (4)0.0387 (4)0.0482 (4)0.0151 (3)0.0101 (3)0.0186 (3)
Br20.0496 (4)0.0355 (3)0.0513 (4)0.0073 (3)0.0199 (3)−0.0051 (3)
Br30.0337 (3)0.0415 (3)0.0407 (3)0.0089 (3)0.0043 (2)0.0009 (3)
Br40.0450 (4)0.0397 (3)0.0446 (4)0.0155 (3)0.0205 (3)0.0109 (3)
Cu10.0331 (4)0.0319 (4)0.0336 (4)0.0095 (3)0.0084 (3)0.0061 (3)
N10.062 (5)0.074 (5)0.060 (4)0.022 (4)−0.024 (4)−0.017 (4)
N20.034 (3)0.058 (3)0.042 (3)0.002 (3)0.004 (2)0.003 (3)
N30.053 (4)0.045 (3)0.040 (3)0.002 (3)0.003 (3)0.009 (3)
N40.050 (3)0.035 (3)0.036 (3)0.005 (2)0.005 (2)0.005 (2)
C10.078 (6)0.075 (5)0.050 (4)0.052 (5)0.000 (4)−0.010 (4)
C20.041 (4)0.077 (5)0.048 (4)0.031 (4)0.014 (3)0.001 (4)
C30.028 (3)0.046 (3)0.034 (3)0.019 (3)0.005 (2)0.006 (3)
C40.040 (4)0.060 (4)0.036 (3)0.005 (3)0.010 (3)0.007 (3)
C50.043 (5)0.083 (6)0.059 (5)0.004 (4)−0.005 (4)0.014 (5)
C60.054 (5)0.063 (5)0.074 (5)−0.005 (4)0.001 (4)0.029 (4)
C70.058 (5)0.068 (5)0.052 (4)0.009 (4)−0.003 (4)−0.011 (4)
C80.060 (5)0.030 (3)0.048 (4)0.008 (3)−0.003 (3)0.003 (3)
C90.050 (4)0.041 (3)0.031 (3)0.014 (3)0.000 (3)−0.003 (3)
C100.028 (3)0.036 (3)0.030 (3)0.004 (2)−0.007 (2)0.001 (3)
C110.037 (3)0.037 (3)0.034 (3)0.005 (3)0.000 (3)−0.003 (3)
C120.038 (4)0.069 (5)0.031 (3)0.015 (3)0.002 (3)0.000 (3)
C130.060 (5)0.070 (5)0.037 (4)0.009 (4)0.016 (3)0.016 (4)
C140.091 (6)0.022 (3)0.061 (5)0.007 (3)0.000 (4)0.017 (3)

Geometric parameters (Å, °)

Br1—Cu12.4164 (9)C4—H40.9400
Br2—Cu12.4039 (9)C5—H50.9400
Br3—Cu12.3544 (9)C6—H6A0.9700
Br4—Cu12.3662 (9)C6—H6B0.9700
N1—C51.320 (10)C6—H6C0.9700
N1—C11.330 (11)C7—H7A0.9700
N1—H10.8800C7—H7B0.9700
N2—C31.339 (7)C7—H7C0.9700
N2—C61.458 (9)C8—C91.314 (9)
N2—C71.463 (8)C8—H80.9400
N3—C121.342 (8)C9—C101.433 (8)
N3—C81.343 (9)C9—H90.9400
N3—H30.8800C10—C111.410 (8)
N4—C101.338 (7)C11—C121.364 (9)
N4—C141.457 (7)C11—H110.9400
N4—C131.464 (8)C12—H120.9400
C1—C21.334 (10)C13—H13A0.9700
C1—H1A0.9400C13—H13B0.9700
C2—C31.431 (8)C13—H13C0.9700
C2—H20.9400C14—H14A0.9700
C3—C41.404 (8)C14—H14B0.9700
C4—C51.341 (9)C14—H14C0.9700
Br1—Cu1—Br2131.05 (4)N2—C6—H6C109.5
Br1—Cu1—Br399.47 (3)H6A—C6—H6C109.5
Br1—Cu1—Br497.82 (3)H6B—C6—H6C109.5
Br2—Cu1—Br3100.27 (3)N2—C7—H7A109.5
Br2—Cu1—Br497.76 (3)N2—C7—H7B109.5
Br3—Cu1—Br4136.48 (4)H7A—C7—H7B109.5
C5—N1—C1119.7 (7)N2—C7—H7C109.5
C5—N1—H1120.2H7A—C7—H7C109.5
C1—N1—H1120.2H7B—C7—H7C109.5
C3—N2—C6122.6 (6)C9—C8—N3122.3 (6)
C3—N2—C7120.4 (6)C9—C8—H8118.9
C6—N2—C7116.7 (6)N3—C8—H8118.9
C12—N3—C8119.5 (6)C8—C9—C10120.8 (6)
C12—N3—H3120.2C8—C9—H9119.6
C8—N3—H3120.2C10—C9—H9119.6
C10—N4—C14122.4 (5)N4—C10—C11122.2 (5)
C10—N4—C13122.4 (5)N4—C10—C9121.7 (5)
C14—N4—C13115.2 (6)C11—C10—C9116.1 (6)
C2—C1—N1122.3 (7)C12—C11—C10119.2 (5)
C2—C1—H1A118.9C12—C11—H11120.4
N1—C1—H1A118.9C10—C11—H11120.4
C1—C2—C3119.6 (7)N3—C12—C11122.1 (6)
C1—C2—H2120.2N3—C12—H12118.9
C3—C2—H2120.2C11—C12—H12118.9
N2—C3—C4123.4 (5)N4—C13—H13A109.5
N2—C3—C2120.7 (6)N4—C13—H13B109.5
C4—C3—C2116.0 (6)H13A—C13—H13B109.5
C5—C4—C3119.5 (6)N4—C13—H13C109.5
C5—C4—H4120.2H13A—C13—H13C109.5
C3—C4—H4120.2H13B—C13—H13C109.5
N1—C5—C4122.9 (8)N4—C14—H14A109.5
N1—C5—H5118.5N4—C14—H14B109.5
C4—C5—H5118.5H14A—C14—H14B109.5
N2—C6—H6A109.5N4—C14—H14C109.5
N2—C6—H6B109.5H14A—C14—H14C109.5
H6A—C6—H6B109.5H14B—C14—H14C109.5
C5—N1—C1—C2−0.1 (12)C12—N3—C8—C90.2 (10)
N1—C1—C2—C3−0.9 (11)N3—C8—C9—C100.5 (10)
C6—N2—C3—C4176.1 (7)C14—N4—C10—C111.6 (9)
C7—N2—C3—C42.7 (9)C13—N4—C10—C11−179.0 (5)
C6—N2—C3—C2−4.6 (9)C14—N4—C10—C9−178.1 (6)
C7—N2—C3—C2−178.0 (6)C13—N4—C10—C91.3 (8)
C1—C2—C3—N2−178.2 (6)C8—C9—C10—N4179.0 (6)
C1—C2—C3—C41.2 (9)C8—C9—C10—C11−0.7 (8)
N2—C3—C4—C5178.9 (6)N4—C10—C11—C12−179.6 (5)
C2—C3—C4—C5−0.5 (9)C9—C10—C11—C120.2 (8)
C1—N1—C5—C40.8 (12)C8—N3—C12—C11−0.8 (9)
C3—C4—C5—N1−0.4 (11)C10—C11—C12—N30.6 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.543.380 (7)162
N3—H3···Br20.882.653.449 (6)152

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2503).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Coffey, T., Robinson, W. T. & Turnbull, M. M. (1996). Acta Cryst. C52, 248–250.
  • Haddad, S. F. & Al-Far, R. H. (2008). J. Chem. Crystallogr.38, 663–669.
  • Luque, A., Sertucha, J., Castillo, O. & Roman, P. (2001). New J. Chem.25, 1208–1214.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Willet, R. D., Awwadi, F., Butcher, R., Haddad, S. & Twamley, B. (2003). Cryst. Growth Des.3, 301–311.
  • Willett, R. D., Haddad, S. F. & Twamley, B. (2000). Acta Cryst. C56, e437.

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