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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages m73-m74
doi:10.1107/S1600536808041652

Bis(2-amino-4-methyl­pyridinium) tetra­chloridocuprate(II)

Rawhi H. Al-Fara and Basem Fares Alib*

aFaculty of Information Technology and Science, Al-Balqa'a Applied University, Salt, Jordan, and bDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan
*Correspondence e-mail: bfali@aabu.edu.jo

(Received 14 November 2008; accepted 8 December 2008; online 17 December 2008)

The asymmetric unit of the title compound, (C6H9N2)2[CuCl4], consists of one cation and one half-anion, bis­ected by a twofold rotation axis through the metal center. The anion exhibits a geometry that is inter­mediate between a Td and D4h arrangement about the Cu atom. The crystal structure contains chains of cations alternating with stacks of anions. The cationic groups inter­act via offset face-to-face π–π stacking, forming chains running along the c axis. The anion stacks are parallel to the cation chains, with no significant inter- nor intra­stack Cl⋯Cl inter­actions. There are several anion–cation hydrogen-bonding inter­actions of the (N—H)pyridine⋯Cl and (N—H)amino⋯Cl types, connecting the chains of cations to the stacks of anions. Both the N—H⋯Cl and π–π stacking inter­actions [centroid–centroid distances 3.61 (8) and 3.92 (2) Å] contribute to the formation of a three-dimensional supra­molecular architecture.

Related literature

For related literature on organic–inorganic hybrids, see: Al-Far, Ali & Haddad (2008[Al-Far, R. H., Ali, B. F. & Haddad, S. F. (2008). Acta Cryst. E64, m689-m690.]); Ali & Al-Far (2007[Ali, B. F. & Al-Far, R. (2007). Acta Cryst. C63, m451-m453.], 2008[Ali, B. F. & Al-Far, R. (2008). J. Chem. Crystallogr. 38, 689-693.]); Coffey et al. (2000[Coffey, T. J., Landee, C. P., Robinson, W. T., Turnbull, M. M., Winn, M. & Woodward, F. M. (2000). Inorg. Chim. Acta, 303, 54-60.]). For bond-length and angle data, see: Raithby et al. (2000[Raithby, P. R., Shields, G. P., Allen, F. H. & Motherwell, W. D. S. (2000). Acta Cryst. B56, 444-454.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • (C6H9N2)2[CuCl4]

  • Mr = 423.65

  • Monoclinic, C 2/c

  • a = 11.313 (3) Å

  • b = 12.272 (3) Å

  • c = 14.264 (4) Å

  • β = 113.201 (17)°

  • V = 1820.2 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.78 mm−1

  • T = 293 (2) K

  • 0.35 × 0.06 × 0.06 mm
Data collection

  • Siemens P4 diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.874, Tmax = 0.898

  • 2039 measured reflections

  • 1590 independent reflections

  • 841 reflections with I > 2σ(I)

  • Rint = 0.058

  • 3 standard reflections every 97 reflections intensity decay: none
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.145

  • S = 0.99

  • 1590 reflections

  • 97 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Selected geometric parameters (Å, °)

Cu1—Cl1 2.2614 (19)
Cu1—Cl2 2.2698 (19)
Cl1i—Cu1—Cl1 94.33 (10)
Cl1—Cu1—Cl2 146.17 (8)
Symmetry code: (i) [-x+1, y, -z+{\script{3\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯Cl1 0.86 2.65 3.407 (6) 147
N1—H1A⋯Cl2i 0.86 2.70 3.360 (6) 134
N2—H2A⋯Cl1 0.86 2.50 3.294 (6) 153
N2—H2B⋯Cl2ii 0.86 2.53 3.359 (6) 164
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: XSCANS (Bruker, 1996[Bruker (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808041652/bg2228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041652/bg2228Isup2.hkl

checkCIF report


Comment top

Hybrid organic-inorganic low dimensional magnetic lattices of the formula (cation)2[MX4] are of special interest (Coffey et al., 2000; and references therein). A wide variety of these complexes are known. Some examples are those containing a protonated pyridine and 2-aminopyrimidine (Coffey et al., 2000). The magnetic exchange in these compounds is mediated by van der Waals contacts between the halide ions of the [MX4]2- pseudo-tetrahedra and the contacts are determined by the crystal packing. In connection with ongoing studies (Al-Far et al., 2008; Ali & Al-Far 2008; Ali & Al-Far 2007) of the structural aspects of organic-inorganic hybrids, here we report the crystal structure of Cu(II)-chloride complex with 2-amino-4-methylpyridinium as the organic cation.

The asymmetric unit in I contains one half anion (bisected by a two fold axis through the metal) and one cation (Fig. 1). The Cu—Cl distances and Cl—Cu—Cl, angles, Table 1, fall in the range reported previously for compounds containing Cu—Cl anions (Raithby et al., 2000). The CuCl42- anion geometry is an intermediate between regular tetrahedral (Td) and square planar (D4 h); the geometry of CuX42- anions will always distort from Td due to the Jahn-Teller effect, and this generally results in a compressed tetrahedral geometry. The extent of this compression is determined principally by electrostatic interactions with the environment – in this case, the hydrogen bonding.

In the cation bond lengths and angles are in accordance with normal values (Allen et. al., 1987).

The crystal packing (Fig. 2) show alternating stacks of anions and chains of cations. The anion stacks are parallel to the cation chains, with no significant inter- and intra-stack Cl···Cl interactions. The cations interact via offset face-to-face, π–π stacking interactions leading to chains along the crystallographic c axis (Fig. 3), with alternating rings centroids separation distances of 3.61 (8) and 3.92 (2) Å.

There are extensive cation···anion intermolecular interactions (Table 2; Fig. 1). In these interactions H1A is involved in a bifurcated hydrogen bonding motif with Cl and Cl2i [N1—H1A···(Cl1,Cl2i) distances are 3.407 (6) and 3.360 (6) Å, respectively, with N1—H1A···(Cl1,Cl2i) angles being 147 and 134°; Symmetry codes: (i) -x + 1, y, -z + 3/2]. The other interactions result between N2—H2A···Cl1 [N1···Cl1 distance is 3.294 (6) and N2—H2A···Cl1 angle of 153°] and N2—H2B···Cl2ii [with N2···Cl2ii distance of 3.359 (6) Å and N2—H2B···Cl2ii angle being 164°; Symmetry code: (ii) -x + 3/2, y - 1/2, -z + 3/2]. These interactions and the symmetrically related ones connect the anion to four surrounding cations.

Both N—H···Cl and π–π stacking interactions cause to the formation of a three-dimensional supramolecular architecture.

Related literature top

For related literature on organic–inorganic hybrids, see: Al-Far, Ali & Haddad (2008); Ali & Al-Far (2007, 2008); Coffey et al. (2000). For bond-length and angle data, see: Raithby et al. (2000); Allen et al. (1987).

Experimental top

To a hot solution (100 °C) of 2-Amino-4-methylpyridine (1 mmol) in 5 ml of CH3CN acidified with 2 ml of 3 M HCl, CuCl2.2H2O (1 mmol) dissolved in 10 ml CH3CN was added. The resulting mixture was refluxed for 1.5 h. The solution was then allowed to stand undisturbed at room temperature. After 24 h yellow parallelepiped crystals were formed (yield: 0.170 g; 80.2%).

Refinement top

Hydrogen atoms were positioned geometrically, with N—H = 0.86 Å, C—H = 0.93 Å for aromatic H and C—H = 0.96 Å for methyl H, and constrained to ride on their parent atoms, Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Sheldrick, 2008); data reduction: SHELXTL (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, viewed down c. Displacement ellipsoids are drawn at the 50% probability level. N—H···Cl—Cu intermolecular interactions are shown as dashed lines. Symmetry operations: (i) -x + 1, y, -z + 3/2; (iii) -1/2 + x, 1/2 + y, z; (iv) 3/2 - x, 1/2 + y, 3/2 - z. H atoms not involved in hydrogen bonding omitted for clarity.
[Figure 2] Fig. 2. Crystal packing diagram showing alternating stacks of anions and chains of cations.
[Figure 3] Fig. 3. Cationic chains along the crystallographic c axis, assembled via offset face-to-face (π–π stacking; double broken lines) motifs. Centroids separation distances are X2(2 - x, y, 3/2 - z)···X1 (x, y, z)···X3(2 - x, - y, 2 - z) are 3.61 (8) and 3.92 (2) Å, respectively.
Bis(2-amino-4-methylpyridinium) tetrachloridocuprate(II) top
Crystal data top
(C6H9N2)2[CuCl4]F(000) = 860
Mr = 423.65Dx = 1.546 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 290 reflections
a = 11.313 (3) Åθ = 2.5–27.3°
b = 12.272 (3) ŵ = 1.78 mm−1
c = 14.264 (4) ÅT = 293 K
β = 113.201 (17)°Parallelepiped, yellow
V = 1820.2 (9) Å30.35 × 0.06 × 0.06 mm
Z = 4
Data collection top
Siemens P4
diffractometer		841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω scansh = −1→13
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −14→1
Tmin = 0.874, Tmax = 0.898l = −16→16
2039 measured reflections3 standard reflections every 97 reflections
1590 independent reflections intensity decay: none
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0577P)2]
where P = (Fo2 + 2Fc2)/3
1590 reflections(Δ/σ)max < 0.001
97 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
(C6H9N2)2[CuCl4]V = 1820.2 (9) Å3
Mr = 423.65Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.313 (3) ŵ = 1.78 mm−1
b = 12.272 (3) ÅT = 293 K
c = 14.264 (4) Å0.35 × 0.06 × 0.06 mm
β = 113.201 (17)°
Data collection top
Siemens P4
diffractometer		841 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		Rint = 0.058
Tmin = 0.874, Tmax = 0.8983 standard reflections every 97 reflections
2039 measured reflections intensity decay: none
1590 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 0.99Δρmax = 0.40 e Å−3
1590 reflectionsΔρmin = −0.37 e Å−3
97 parameters
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
Cu10.50000.00098 (10)0.75000.0539 (4)
Cl10.64416 (17)−0.12430 (14)0.74530 (17)0.0716 (7)
N10.9282 (5)0.0108 (5)0.8601 (4)0.0552 (15)
H1A0.84730.00000.84320.066*
Cl20.35031 (15)0.12618 (14)0.66064 (15)0.0632 (6)
C21.0055 (6)−0.0772 (6)0.8719 (5)0.0487 (18)
N20.9548 (6)−0.1746 (5)0.8554 (5)0.0736 (19)
H2A0.8732−0.18250.83720.088*
H2B1.0030−0.23090.86260.088*
C31.1373 (6)−0.0577 (6)0.9018 (5)0.0551 (19)
H3A1.1933−0.11610.91160.066*
C41.1850 (7)0.0474 (7)0.9168 (5)0.0584 (19)
C51.0969 (9)0.1339 (6)0.9006 (6)0.072 (2)
H5A1.12580.20570.90890.087*
C60.9713 (9)0.1124 (6)0.8733 (6)0.071 (2)
H6A0.91380.16970.86360.085*
C71.3250 (7)0.0704 (8)0.9462 (7)0.095 (3)
H7A1.36910.00380.94540.143*
H7B1.36040.10131.01340.143*
H7C1.33520.12090.89850.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0460 (7)0.0348 (6)0.0783 (9)0.0000.0215 (6)0.000
Cl10.0511 (11)0.0382 (10)0.1332 (19)−0.0006 (8)0.0444 (11)−0.0103 (11)
N10.049 (3)0.052 (4)0.064 (4)0.006 (3)0.022 (3)−0.005 (3)
Cl20.0447 (10)0.0374 (10)0.0867 (14)−0.0050 (8)0.0037 (8)0.0074 (9)
C20.050 (4)0.046 (4)0.049 (4)0.004 (4)0.020 (3)0.000 (3)
N20.059 (4)0.043 (4)0.121 (6)−0.008 (3)0.038 (4)−0.007 (4)
C30.057 (5)0.049 (5)0.062 (5)0.007 (4)0.027 (4)−0.002 (4)
C40.063 (5)0.058 (5)0.055 (5)−0.007 (4)0.023 (4)0.002 (4)
C50.097 (7)0.041 (5)0.080 (6)−0.006 (5)0.035 (5)−0.003 (4)
C60.073 (6)0.049 (5)0.085 (6)0.008 (5)0.026 (5)−0.004 (5)
C70.078 (6)0.104 (8)0.109 (7)−0.038 (6)0.044 (6)−0.031 (6)
Geometric parameters (Å, º) top
Cu1—Cl1i2.2615 (19)C3—C41.381 (9)
Cu1—Cl12.2614 (19)C3—H3A0.9300
Cu1—Cl2i2.2698 (19)C4—C51.412 (10)
Cu1—Cl22.2698 (19)C4—C71.496 (10)
N1—C61.326 (9)C5—C61.343 (11)
N1—C21.358 (8)C5—H5A0.9300
N1—H1A0.8600C6—H6A0.9300
C2—N21.307 (8)C7—H7A0.9600
C2—C31.400 (9)C7—H7B0.9600
N2—H2A0.8600C7—H7C0.9600
N2—H2B0.8600
Cl1i—Cu1—Cl194.33 (10)C2—C3—H3A119.6
Cl1i—Cu1—Cl2i146.17 (8)C3—C4—C5118.0 (7)
Cl1—Cu1—Cl2i95.15 (7)C3—C4—C7121.7 (7)
Cl1i—Cu1—Cl295.15 (6)C5—C4—C7120.3 (8)
Cl1—Cu1—Cl2146.17 (8)C6—C5—C4119.8 (8)
Cl2i—Cu1—Cl294.80 (10)C6—C5—H5A120.1
C6—N1—C2123.2 (7)C4—C5—H5A120.1
C6—N1—H1A118.4N1—C6—C5120.9 (8)
C2—N1—H1A118.4N1—C6—H6A119.5
N2—C2—N1119.3 (6)C5—C6—H6A119.5
N2—C2—C3123.4 (7)C4—C7—H7A109.5
N1—C2—C3117.3 (7)C4—C7—H7B109.5
C2—N2—H2A120.0H7A—C7—H7B109.5
C2—N2—H2B120.0C4—C7—H7C109.5
H2A—N2—H2B120.0H7A—C7—H7C109.5
C4—C3—C2120.8 (7)H7B—C7—H7C109.5
C4—C3—H3A119.6
C6—N1—C2—N2−178.6 (7)C2—C3—C4—C7−178.4 (7)
C6—N1—C2—C31.5 (10)C3—C4—C5—C61.2 (11)
N2—C2—C3—C4179.1 (7)C7—C4—C5—C6179.3 (8)
N1—C2—C3—C4−1.0 (10)C2—N1—C6—C5−0.6 (12)
C2—C3—C4—C5−0.3 (11)C4—C5—C6—N1−0.8 (12)
Symmetry code: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.862.653.407 (6)147
N1—H1A···Cl2i0.862.703.360 (6)134
N2—H2A···Cl10.862.503.294 (6)153
N2—H2B···Cl2ii0.862.533.359 (6)164
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula(C6H9N2)2[CuCl4]
Mr423.65
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)11.313 (3), 12.272 (3), 14.264 (4)
β (°) 113.201 (17)
V (Å3)1820.2 (9)
Z4
Radiation typeMo Kα
µ (mm−1)1.78
Crystal size (mm)0.35 × 0.06 × 0.06
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.874, 0.898
No. of measured, independent and
observed [I > 2σ(I)] reflections		2039, 1590, 841
Rint0.058
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.145, 0.99
No. of reflections1590
No. of parameters97
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.40, −0.37

Computer programs: XSCANS (Bruker, 1996), XSCANS (Sheldrick, 2008), SHELXTL (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Cu1—Cl12.2614 (19)Cu1—Cl22.2698 (19)
Cl1i—Cu1—Cl194.33 (10)Cl1—Cu1—Cl2146.17 (8)
Symmetry code: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.862.653.407 (6)147.3
N1—H1A···Cl2i0.862.703.360 (6)134.3
N2—H2A···Cl10.862.503.294 (6)153.2
N2—H2B···Cl2ii0.862.533.359 (6)163.7
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2.
 

Acknowledgements

This research was supported by Al al-Bayt University and Al-Balqa'a Applied University.

References

First citationAl-Far, R. H., Ali, B. F. & Haddad, S. F. (2008). Acta Cryst. E64, m689–m690.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationAli, B. F. & Al-Far, R. (2007). Acta Cryst. C63, m451–m453.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationAli, B. F. & Al-Far, R. (2008). J. Chem. Crystallogr. 38, 689–693.  Web of Science CSD CrossRef CAS Google Scholar
 First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBruker (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.  Google Scholar
 First citationCoffey, T. J., Landee, C. P., Robinson, W. T., Turnbull, M. M., Winn, M. & Woodward, F. M. (2000). Inorg. Chim. Acta, 303, 54–60.  Web of Science CSD CrossRef CAS Google Scholar
 First citationRaithby, P. R., Shields, G. P., Allen, F. H. & Motherwell, W. D. S. (2000). Acta Cryst. B56, 444–454.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Pages m73-m74
doi:10.1107/S1600536808041652
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