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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2108
https://doi.org/10.1107/S1600536810028734

4-Amino­pyridinium 4-carb­­oxy­butano­ate

Hoong-Kun Fun,a*‡ Madhukar Hemamalinia and Venkatachalam Rajakannanb

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bBiomedical Structural Biology, School of Biological Sciences, Nanyang Technological University, Singapore 138673
*Correspondence e-mail: hkfun@usm.my

(Received 12 July 2010; accepted 19 July 2010; online 24 July 2010)

The asymmetric unit of the title salt, C5H7N2+·C5H7O4−, contains two 4-amino­pyridinium cations and two 4-carb­oxy­butano­ate anions. Each 4-amino­pyridinium cation is planar, with a maximum deviation of 0.005 (2) Å. Both 4-carb­oxy­butano­ate anions adopt an extended conformation. In the crystal structure, the cations and anions are linked via N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological activity of 4-amino­pyridine, see: Schwid et al. (1997[Schwid, S. R., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817-821.]). For crystal structure determinations of 4-amino­pyridine, see: Chao & Schempp (1977[Chao, M. & Schempp, E. (1977). Acta Cryst. B33, 1557-1564.]); Anderson et al. (2005[Anderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350-o1353.]). For conformations of 4-carb­oxy­butano­ate (hydrogen glutarate) anions, see: Saraswathi et al. (2001[Saraswathi, N. T., Manoj, N. & Vijayan, M. (2001). Acta Cryst. B57, 366-371.]).

[Scheme 1]

Experimental

Crystal data

  • C5H7N2+·C5H7O4−

  • Mr = 226.23

  • Monoclinic, P 21 /c

  • a = 9.6159 (2) Å

  • b = 10.3065 (2) Å

  • c = 22.6801 (5) Å

  • β = 102.143 (1)°

  • V = 2197.45 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 296 K

  • 0.35 × 0.26 × 0.21 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.978

  • 7931 measured reflections

  • 7931 independent reflections

  • 5556 reflections with I > 2σ(I)
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.154

  • S = 1.04

  • 7931 reflections

  • 290 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1O1⋯O1Bi 0.89 1.57 2.4591 (17) 172
N1A—H1AA⋯O1Bii 0.86 2.59 3.183 (2) 127
N1A—H1AA⋯O2Bii 0.86 1.87 2.729 (2) 177
N2A—H2AC⋯O2Aiii 0.86 2.18 2.9627 (19) 151
N2A—H2AD⋯O4B 0.86 2.10 2.948 (2) 170
O3B—H1O3⋯O3Aiv 0.92 1.56 2.4791 (17) 176
C10A—H10A⋯O4Bv 0.93 2.55 3.161 (2) 124
C7A—H7AA⋯O3B 0.93 2.47 3.370 (2) 162
Symmetry codes: (i) x-1, y+1, z-1; (ii) x-1, y+1, z; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) x, y, z+1; (v) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028734/wn2401sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028734/wn2401Isup2.hkl

checkCIF report


Comment top

4-Aminopyridine (fampridine) is used in the treatment of neurological ailments, such as multiple sclerosis (MS), with tests showing that fampridine improves motor function in MS patients (Schwid et al., 1997). The room temperature crystal structure of 4-aminopyridine was reported many years ago (Chao & Schempp, 1977); a redetermination at low temperature has been reported more recently (Anderson et al., 2005). Aliphatic dicarboxylic acids, HOOC(CH2)nCOOH, exhibit interesting complexing properties. This is due to the flexibility of the ligand which may be completely or only partially deprotonated. Glutaric acid (1,3-propanedicarboxylic acid) is a white crystalline solid which is very soluble in water. The compound is a useful building block for polymers, an intermediate in chemical synthesis and it is used in the manufacture of an antiretroviral drug. The compound is also used in solder flux. The present study has been carried out to study the hydrogen bonding patterns present in the crystal structure of 4-aminopyridinium 4-carboxybutanoate.

The asymmetric unit of the title compound consists of two crystallographically independent 4-aminopyridinium cations (A and B) and 4-carboxybutanoate (hydrogen glutarate) anions (A and B) (Fig. 1). Each 4-aminopyridinium cation is planar, with a maximum deviation of 0.005 (2) Å for atom C7A in cation A and 0.005 (2) Å for atom C9B in cation B. In the cations, protonation at atoms N1A and N1B lead to a slight increase in the C6A—N1A—C10A [120.06 (16)°] and C6B—N1B—C10B [120.21 (16)°] angles compared to those observed in the unprotonated structure of 4-aminopyridine (Anderson et al., 2005). The conformations of the 4-carboxybutanoate anions can be described by the two torsion angles C1A—C2A—C3A—C4A of 175.44 (15)° and C2A—C3A—C4A—C5A of 174.42 (15)° in anion A; C1B—C2B—C3B—C4B of -175.99 (14)° and C2B—C3B—C4B—C5B of -176.94 (15)° in anion B. These torsion angles indicate that both anions adopt fully extended conformations (Saraswathi et al., 2001).

In the crystal structure (Fig. 2), the cations and anions are linked via O1A—H1O1···O1B, N1A—H1AA···O1B, N1A—H1AA···O2B, N2A—H2AC···O2A, N2A—H2AD···O4B, O3B—H1O3···O3A, C10A—H10A···O4B and C7A—H7AA···03B intermolecular hydrogen bonds (Table 1), forming a two-dimensional network parallel to the bc-plane.

The crystal structure is a merohedral twin, with BASF = 0.3214 (15).

Related literature top

For the biological activity of 4-aminopyridine, see: Schwid et al. (1997). For crystal structure determinations of 4-aminopyridine, see: Chao & Schempp (1977); Anderson et al. (2005). For conformations of 4-carboxybutanoate (hydrogen glutarate) anions, see: Saraswathi et al. (2001).

Experimental top

A hot methanol solution (20 ml) of 4-aminopyridine (0.0471 g, Aldrich) and glutaric acid (0.0661 g, Merck) was warmed for half an hour over a water bath. The mixture was cooled slowly and kept at room temperature. Colourless crystals were obtained after a few days.

Refinement top

Oxygen-bound H atoms were located in a difference map [O—H = 0.8903 and 0.9176 Å]. Nitrogen- and carbon-bound H atoms were positioned geometrically [N—H = 0.86 Å and C—H = 0.93–0.97 Å]. All hydrogen atoms were refined using a riding model, with Uiso(H) = 1.2 Ueq(C).

Structure description top

4-Aminopyridine (fampridine) is used in the treatment of neurological ailments, such as multiple sclerosis (MS), with tests showing that fampridine improves motor function in MS patients (Schwid et al., 1997). The room temperature crystal structure of 4-aminopyridine was reported many years ago (Chao & Schempp, 1977); a redetermination at low temperature has been reported more recently (Anderson et al., 2005). Aliphatic dicarboxylic acids, HOOC(CH2)nCOOH, exhibit interesting complexing properties. This is due to the flexibility of the ligand which may be completely or only partially deprotonated. Glutaric acid (1,3-propanedicarboxylic acid) is a white crystalline solid which is very soluble in water. The compound is a useful building block for polymers, an intermediate in chemical synthesis and it is used in the manufacture of an antiretroviral drug. The compound is also used in solder flux. The present study has been carried out to study the hydrogen bonding patterns present in the crystal structure of 4-aminopyridinium 4-carboxybutanoate.

The asymmetric unit of the title compound consists of two crystallographically independent 4-aminopyridinium cations (A and B) and 4-carboxybutanoate (hydrogen glutarate) anions (A and B) (Fig. 1). Each 4-aminopyridinium cation is planar, with a maximum deviation of 0.005 (2) Å for atom C7A in cation A and 0.005 (2) Å for atom C9B in cation B. In the cations, protonation at atoms N1A and N1B lead to a slight increase in the C6A—N1A—C10A [120.06 (16)°] and C6B—N1B—C10B [120.21 (16)°] angles compared to those observed in the unprotonated structure of 4-aminopyridine (Anderson et al., 2005). The conformations of the 4-carboxybutanoate anions can be described by the two torsion angles C1A—C2A—C3A—C4A of 175.44 (15)° and C2A—C3A—C4A—C5A of 174.42 (15)° in anion A; C1B—C2B—C3B—C4B of -175.99 (14)° and C2B—C3B—C4B—C5B of -176.94 (15)° in anion B. These torsion angles indicate that both anions adopt fully extended conformations (Saraswathi et al., 2001).

In the crystal structure (Fig. 2), the cations and anions are linked via O1A—H1O1···O1B, N1A—H1AA···O1B, N1A—H1AA···O2B, N2A—H2AC···O2A, N2A—H2AD···O4B, O3B—H1O3···O3A, C10A—H10A···O4B and C7A—H7AA···03B intermolecular hydrogen bonds (Table 1), forming a two-dimensional network parallel to the bc-plane.

The crystal structure is a merohedral twin, with BASF = 0.3214 (15).

For the biological activity of 4-aminopyridine, see: Schwid et al. (1997). For crystal structure determinations of 4-aminopyridine, see: Chao & Schempp (1977); Anderson et al. (2005). For conformations of 4-carboxybutanoate (hydrogen glutarate) anions, see: Saraswathi et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing, showing hydrogen-bonded (dashed lines) 2D networks parallel to to the bc-plane. H atoms not involved in the intermolecular interactions have been omitted for clarity.
4-Aminopyridinium 4-carboxybutanoate top
Crystal data top
C5H7N2+·C5H7O4−F(000) = 960
Mr = 226.23Dx = 1.368 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8906 reflections
a = 9.6159 (2) Åθ = 2.5–30.1°
b = 10.3065 (2) ŵ = 0.11 mm−1
c = 22.6801 (5) ÅT = 296 K
β = 102.143 (1)°Block, colourless
V = 2197.45 (8) Å30.35 × 0.26 × 0.21 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		7931 independent reflections
Radiation source: fine-focus sealed tube5556 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 32.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −14→14
Tmin = 0.963, Tmax = 0.978k = −15→15
7931 measured reflectionsl = −11→34
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0758P)2 + 0.2205P]
where P = (Fo2 + 2Fc2)/3
7931 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C5H7N2+·C5H7O4−V = 2197.45 (8) Å3
Mr = 226.23Z = 8
Monoclinic, P21/cMo Kα radiation
a = 9.6159 (2) ŵ = 0.11 mm−1
b = 10.3065 (2) ÅT = 296 K
c = 22.6801 (5) Å0.35 × 0.26 × 0.21 mm
β = 102.143 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		7931 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		5556 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.978Rint = 0.000
7931 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å−3
7931 reflectionsΔρmin = −0.20 e Å−3
290 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A0.28193 (16)1.02435 (13)0.06872 (6)0.0516 (3)
H1O10.25301.01610.02890.077*
O2A0.41099 (16)0.95000 (13)0.15319 (5)0.0478 (3)
O3A0.76925 (16)0.49292 (13)0.05256 (5)0.0528 (4)
O4A0.74003 (16)0.55719 (12)0.14167 (5)0.0454 (3)
C1A0.3787 (2)0.94695 (15)0.09826 (7)0.0352 (3)
C2A0.4485 (2)0.85513 (16)0.06135 (7)0.0370 (3)
H2AA0.50280.90590.03810.044*
H2AB0.37450.81030.03300.044*
C3A0.5465 (2)0.75453 (16)0.09724 (7)0.0352 (3)
H3AA0.62640.79760.12300.042*
H3AB0.49550.70640.12270.042*
C4A0.60070 (19)0.66165 (16)0.05536 (7)0.0366 (3)
H4AA0.52020.61440.03220.044*
H4AB0.64150.71210.02710.044*
C5A0.7105 (2)0.56458 (15)0.08576 (7)0.0346 (3)
N1A0.28175 (17)0.87243 (15)0.83697 (7)0.0449 (4)
H1AA0.22640.92790.84860.054*
N2A0.53978 (18)0.60387 (16)0.78136 (7)0.0499 (4)
H2AC0.53410.59180.74340.060*
H2AD0.59870.55900.80720.060*
C6A0.3744 (2)0.80430 (19)0.87789 (8)0.0488 (4)
H6AA0.37780.81910.91860.059*
C7A0.4634 (2)0.71465 (18)0.86214 (8)0.0461 (4)
H7AA0.52680.66920.89150.055*
C8A0.45783 (19)0.69135 (17)0.79991 (8)0.0379 (3)
C9A0.3609 (2)0.76547 (17)0.75810 (7)0.0399 (4)
H9AA0.35480.75430.71690.048*
C10A0.2754 (2)0.85416 (19)0.77826 (8)0.0434 (4)
H10A0.21150.90270.75040.052*
O1B1.22169 (16)−0.01002 (13)0.95900 (5)0.0527 (4)
O2B1.10552 (17)0.05354 (13)0.86994 (5)0.0494 (3)
O3B0.72084 (16)0.52422 (13)0.94174 (6)0.0532 (4)
H1O30.73470.51450.98280.080*
O4B0.76125 (17)0.44368 (13)0.85744 (5)0.0524 (3)
C1B1.12988 (19)0.06276 (15)0.92524 (7)0.0359 (3)
C2B1.05243 (19)0.16092 (15)0.95600 (7)0.0357 (3)
H2BA1.12230.21270.98310.043*
H2BB0.99660.11480.98030.043*
C3B0.9547 (2)0.25132 (15)0.91350 (7)0.0342 (3)
H3BA0.87920.20160.88840.041*
H3BB1.00790.29480.88740.041*
C4B0.89090 (19)0.35155 (16)0.94935 (7)0.0361 (3)
H4BA0.84410.30630.97730.043*
H4BB0.96770.40230.97310.043*
C5B0.7856 (2)0.44294 (16)0.91214 (7)0.0358 (3)
N1B−0.04752 (17)0.37734 (15)0.17394 (7)0.0453 (4)
H1BA−0.11370.43330.16190.054*
N2B0.26087 (18)0.10594 (16)0.23042 (7)0.0494 (4)
H2BC0.29140.09280.26840.059*
H2BD0.29460.06130.20460.059*
C6B0.0019 (2)0.35827 (19)0.23332 (8)0.0440 (4)
H6BA−0.03480.40670.26110.053*
C7B0.1058 (2)0.26829 (17)0.25317 (7)0.0402 (4)
H7BA0.13920.25600.29430.048*
C8B0.16224 (19)0.19448 (17)0.21178 (7)0.0377 (3)
C9B0.1092 (2)0.21875 (18)0.14972 (8)0.0463 (4)
H9BA0.14440.17340.12060.056*
C10B0.0059 (2)0.30944 (19)0.13355 (8)0.0494 (5)
H10B−0.02910.32500.09270.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0584 (8)0.0587 (8)0.0349 (6)0.0303 (7)0.0034 (6)−0.0017 (6)
O2A0.0626 (9)0.0535 (7)0.0270 (5)0.0165 (7)0.0085 (6)−0.0009 (5)
O3A0.0656 (9)0.0597 (8)0.0334 (6)0.0320 (7)0.0109 (6)−0.0008 (6)
O4A0.0568 (8)0.0485 (7)0.0289 (6)0.0187 (6)0.0043 (6)−0.0008 (5)
C1A0.0396 (9)0.0387 (8)0.0277 (7)0.0068 (7)0.0083 (6)0.0003 (6)
C2A0.0420 (9)0.0428 (8)0.0262 (7)0.0128 (8)0.0073 (6)0.0014 (6)
C3A0.0401 (8)0.0367 (7)0.0288 (7)0.0081 (6)0.0068 (7)−0.0011 (6)
C4A0.0397 (8)0.0421 (8)0.0274 (7)0.0105 (8)0.0056 (6)−0.0012 (6)
C5A0.0383 (8)0.0351 (7)0.0298 (7)0.0065 (7)0.0056 (6)−0.0012 (6)
N1A0.0506 (9)0.0441 (8)0.0422 (8)0.0090 (7)0.0148 (7)−0.0026 (6)
N2A0.0533 (10)0.0551 (9)0.0386 (8)0.0173 (8)0.0036 (7)−0.0042 (7)
C6A0.0620 (12)0.0484 (10)0.0347 (8)0.0055 (10)0.0071 (8)−0.0039 (7)
C7A0.0564 (12)0.0457 (9)0.0334 (8)0.0097 (9)0.0029 (8)−0.0012 (7)
C8A0.0392 (8)0.0369 (8)0.0362 (8)0.0018 (7)0.0048 (7)−0.0005 (6)
C9A0.0458 (10)0.0465 (9)0.0261 (7)0.0040 (7)0.0044 (7)0.0019 (6)
C10A0.0456 (10)0.0477 (9)0.0375 (8)0.0034 (8)0.0102 (7)0.0027 (7)
O1B0.0608 (8)0.0608 (8)0.0340 (6)0.0342 (7)0.0042 (6)0.0021 (6)
O2B0.0653 (9)0.0533 (7)0.0293 (6)0.0242 (7)0.0094 (6)0.0018 (5)
O3B0.0653 (9)0.0577 (8)0.0353 (6)0.0334 (7)0.0073 (6)0.0009 (6)
O4B0.0659 (9)0.0579 (8)0.0288 (6)0.0227 (7)−0.0008 (6)−0.0005 (5)
C1B0.0407 (9)0.0373 (8)0.0301 (7)0.0084 (7)0.0087 (7)0.0018 (6)
C2B0.0406 (9)0.0380 (8)0.0281 (7)0.0122 (7)0.0063 (6)0.0011 (6)
C3B0.0401 (8)0.0344 (7)0.0273 (7)0.0066 (6)0.0054 (7)−0.0005 (6)
C4B0.0398 (8)0.0389 (7)0.0279 (7)0.0095 (7)0.0032 (6)−0.0035 (6)
C5B0.0387 (9)0.0343 (7)0.0321 (7)0.0076 (7)0.0019 (6)−0.0010 (6)
N1B0.0458 (9)0.0450 (8)0.0424 (8)0.0103 (7)0.0030 (7)0.0035 (6)
N2B0.0553 (10)0.0565 (9)0.0368 (8)0.0171 (8)0.0105 (7)0.0065 (7)
C6B0.0468 (10)0.0480 (9)0.0368 (9)0.0012 (9)0.0078 (7)−0.0046 (7)
C7B0.0461 (10)0.0455 (9)0.0278 (7)0.0047 (8)0.0048 (7)−0.0013 (6)
C8B0.0406 (9)0.0390 (8)0.0342 (8)0.0033 (7)0.0095 (7)0.0019 (6)
C9B0.0577 (12)0.0480 (9)0.0330 (8)0.0116 (9)0.0093 (8)−0.0003 (7)
C10B0.0588 (12)0.0554 (10)0.0325 (9)0.0105 (10)0.0062 (8)0.0045 (8)
Geometric parameters (Å, º) top
O1A—C1A1.299 (2)O1B—C1B1.2823 (19)
O1A—H1O10.8903O2B—C1B1.2303 (19)
O2A—C1A1.2194 (18)O3B—C5B1.310 (2)
O3A—C5A1.269 (2)O3B—H1O30.9176
O4A—C5A1.2423 (18)O4B—C5B1.2133 (19)
C1A—C2A1.511 (2)C1B—C2B1.511 (2)
C2A—C3A1.518 (2)C2B—C3B1.516 (2)
C2A—H2AA0.9700C2B—H2BA0.9700
C2A—H2AB0.9700C2B—H2BB0.9700
C3A—C4A1.516 (2)C3B—C4B1.521 (2)
C3A—H3AA0.9700C3B—H3BA0.9700
C3A—H3AB0.9700C3B—H3BB0.9700
C4A—C5A1.511 (2)C4B—C5B1.505 (2)
C4A—H4AA0.9700C4B—H4BA0.9700
C4A—H4AB0.9700C4B—H4BB0.9700
N1A—C10A1.333 (2)N1B—C10B1.338 (2)
N1A—C6A1.342 (2)N1B—C6B1.345 (2)
N1A—H1AA0.8600N1B—H1BA0.8600
N2A—C8A1.323 (2)N2B—C8B1.320 (2)
N2A—H2AC0.8600N2B—H2BC0.8600
N2A—H2AD0.8600N2B—H2BD0.8600
C6A—C7A1.357 (3)C6B—C7B1.368 (3)
C6A—H6AA0.9300C6B—H6BA0.9300
C7A—C8A1.422 (2)C7B—C8B1.403 (2)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.407 (2)C8B—C9B1.415 (2)
C9A—C10A1.370 (3)C9B—C10B1.357 (3)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—H10A0.9300C10B—H10B0.9300
C1A—O1A—H1O1120.0C5B—O3B—H1O3117.8
O2A—C1A—O1A120.78 (15)O2B—C1B—O1B121.54 (15)
O2A—C1A—C2A122.33 (15)O2B—C1B—C2B121.05 (14)
O1A—C1A—C2A116.89 (13)O1B—C1B—C2B117.40 (13)
C1A—C2A—C3A115.41 (12)C1B—C2B—C3B114.68 (13)
C1A—C2A—H2AA108.4C1B—C2B—H2BA108.6
C3A—C2A—H2AA108.4C3B—C2B—H2BA108.6
C1A—C2A—H2AB108.4C1B—C2B—H2BB108.6
C3A—C2A—H2AB108.4C3B—C2B—H2BB108.6
H2AA—C2A—H2AB107.5H2BA—C2B—H2BB107.6
C4A—C3A—C2A110.61 (12)C2B—C3B—C4B110.07 (12)
C4A—C3A—H3AA109.5C2B—C3B—H3BA109.6
C2A—C3A—H3AA109.5C4B—C3B—H3BA109.6
C4A—C3A—H3AB109.5C2B—C3B—H3BB109.6
C2A—C3A—H3AB109.5C4B—C3B—H3BB109.6
H3AA—C3A—H3AB108.1H3BA—C3B—H3BB108.2
C5A—C4A—C3A115.55 (13)C5B—C4B—C3B115.13 (13)
C5A—C4A—H4AA108.4C5B—C4B—H4BA108.5
C3A—C4A—H4AA108.4C3B—C4B—H4BA108.5
C5A—C4A—H4AB108.4C5B—C4B—H4BB108.5
C3A—C4A—H4AB108.4C3B—C4B—H4BB108.5
H4AA—C4A—H4AB107.5H4BA—C4B—H4BB107.5
O4A—C5A—O3A122.35 (15)O4B—C5B—O3B120.63 (15)
O4A—C5A—C4A119.61 (14)O4B—C5B—C4B122.68 (15)
O3A—C5A—C4A118.04 (13)O3B—C5B—C4B116.69 (13)
C10A—N1A—C6A120.06 (16)C10B—N1B—C6B120.21 (16)
C10A—N1A—H1AA120.0C10B—N1B—H1BA119.9
C6A—N1A—H1AA120.0C6B—N1B—H1BA119.9
C8A—N2A—H2AC120.0C8B—N2B—H2BC120.0
C8A—N2A—H2AD120.0C8B—N2B—H2BD120.0
H2AC—N2A—H2AD120.0H2BC—N2B—H2BD120.0
N1A—C6A—C7A122.55 (17)N1B—C6B—C7B120.57 (17)
N1A—C6A—H6AA118.7N1B—C6B—H6BA119.7
C7A—C6A—H6AA118.7C7B—C6B—H6BA119.7
C6A—C7A—C8A118.83 (17)C6B—C7B—C8B120.38 (16)
C6A—C7A—H7AA120.6C6B—C7B—H7BA119.8
C8A—C7A—H7AA120.6C8B—C7B—H7BA119.8
N2A—C8A—C9A120.67 (16)N2B—C8B—C7B120.90 (15)
N2A—C8A—C7A122.04 (16)N2B—C8B—C9B121.69 (16)
C9A—C8A—C7A117.29 (16)C7B—C8B—C9B117.41 (16)
C10A—C9A—C8A119.73 (16)C10B—C9B—C8B118.75 (17)
C10A—C9A—H9AA120.1C10B—C9B—H9BA120.6
C8A—C9A—H9AA120.1C8B—C9B—H9BA120.6
N1A—C10A—C9A121.52 (17)N1B—C10B—C9B122.66 (17)
N1A—C10A—H10A119.2N1B—C10B—H10B118.7
C9A—C10A—H10A119.2C9B—C10B—H10B118.7
O2A—C1A—C2A—C3A8.1 (3)O2B—C1B—C2B—C3B−4.8 (3)
O1A—C1A—C2A—C3A−172.34 (16)O1B—C1B—C2B—C3B175.08 (17)
C1A—C2A—C3A—C4A175.44 (15)C1B—C2B—C3B—C4B−175.99 (14)
C2A—C3A—C4A—C5A174.42 (15)C2B—C3B—C4B—C5B−176.94 (15)
C3A—C4A—C5A—O4A6.7 (3)C3B—C4B—C5B—O4B−5.5 (3)
C3A—C4A—C5A—O3A−173.38 (17)C3B—C4B—C5B—O3B175.12 (16)
C10A—N1A—C6A—C7A−0.6 (3)C10B—N1B—C6B—C7B−0.9 (3)
N1A—C6A—C7A—C8A−0.3 (3)N1B—C6B—C7B—C8B0.0 (3)
C6A—C7A—C8A—N2A−178.87 (18)C6B—C7B—C8B—N2B−178.91 (18)
C6A—C7A—C8A—C9A1.1 (3)C6B—C7B—C8B—C9B1.0 (3)
N2A—C8A—C9A—C10A178.99 (18)N2B—C8B—C9B—C10B178.79 (18)
C7A—C8A—C9A—C10A−1.0 (3)C7B—C8B—C9B—C10B−1.1 (3)
C6A—N1A—C10A—C9A0.8 (3)C6B—N1B—C10B—C9B0.8 (3)
C8A—C9A—C10A—N1A0.1 (3)C8B—C9B—C10B—N1B0.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1O1···O1Bi0.891.572.4591 (17)172
N1A—H1AA···O1Bii0.862.593.183 (2)127
N1A—H1AA···O2Bii0.861.872.729 (2)177
N2A—H2AC···O2Aiii0.862.182.9627 (19)151
N2A—H2AD···O4B0.862.102.948 (2)170
O3B—H1O3···O3Aiv0.921.562.4791 (17)176
C10A—H10A···O4Bv0.932.553.161 (2)124
C7A—H7AA···O3B0.932.473.370 (2)162
Symmetry codes: (i) x−1, y+1, z−1; (ii) x−1, y+1, z; (iii) x, −y+3/2, z+1/2; (iv) x, y, z+1; (v) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC5H7N2+·C5H7O4−
Mr226.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.6159 (2), 10.3065 (2), 22.6801 (5)
β (°) 102.143 (1)
V (Å3)2197.45 (8)
Z8
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.35 × 0.26 × 0.21
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.963, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		7931, 7931, 5556
Rint0.000
(sin θ/λ)max (Å−1)0.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.154, 1.04
No. of reflections7931
No. of parameters290
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1O1···O1Bi0.89001.57002.4591 (17)172.00
N1A—H1AA···O1Bii0.86002.59003.183 (2)127.00
N1A—H1AA···O2Bii0.86001.87002.729 (2)177.00
N2A—H2AC···O2Aiii0.86002.18002.9627 (19)151.00
N2A—H2AD···O4B0.86002.10002.948 (2)170.00
O3B—H1O3···O3Aiv0.92001.56002.4791 (17)176.00
C10A—H10A···O4Bv0.93002.55003.161 (2)124.00
C7A—H7AA···O3B0.93002.47003.370 (2)162.00
Symmetry codes: (i) x−1, y+1, z−1; (ii) x−1, y+1, z; (iii) x, −y+3/2, z+1/2; (iv) x, y, z+1; (v) −x+1, y+1/2, −z+3/2.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

First citationAnderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350–o1353.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChao, M. & Schempp, E. (1977). Acta Cryst. B33, 1557–1564.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationSaraswathi, N. T., Manoj, N. & Vijayan, M. (2001). Acta Cryst. B57, 366–371.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSchwid, S. R., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817–821.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2108
https://doi.org/10.1107/S1600536810028734
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