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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 68| Part 2| February 2012| Page o358
doi:10.1107/S1600536811055644

Zwitterionic 4-carb­­oxy-2-(1-methyl­pyridin-1-ium-4-yl)-1H-imidazole-5-carboxyl­ate

Dao-Sen Liua* and Jun-Guo Fangb

aCommunication and Electronic Engineering Institute, Qiqihar University, 161006 Qiqihar, Heilongjiang, People's Republic of China, and bThe First High School of Laha, 161342, Nehe, Heilongjiang, People's Republic of China
*Correspondence e-mail: liudaosen66@163.com

(Received 19 December 2011; accepted 26 December 2011; online 11 January 2012)

In the title zwitterionic mol­ecule, C11H9N3O4, the imidazole and pyridine rings form a dihedral angle of 2.60 (2)°. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers. Weak inter­molecular C—H⋯O inter­actions further consolidate the crystal packing.

Related literature

For the use and related structures of the multifunctional connector 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarb­oxy­lic acid in coordination chemistry, see: Sun et al. (2006[Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751-o2752.]); Li et al. (2009a[Li, X., Liu, W., Wu, B.-L. & Zhang, H.-Y. (2009a). Acta Cryst. E65, m820-m821.],b[Li, X., Wu, B. L., Niu, C. Y., Niu, Y. Y. & Zhang, H. Y. (2009b). Cryst. Growth Des. 9, 3423-3431.]); Jing et al. (2010a[Jing, X. M., Meng, H., Li, G. H., Yu, Y., Huo, Q. S., Eddaoudi, M. & Liu, Y. L. (2010a). Cryst. Growth Des. 10, 3489-3495.],b[Jing, X. M., Zhang, L. R., Ma, T. L., Li, G. H., Yu, Y., Huo, Q. S., Eddaoudi, M. & Liu, Y. L. (2010b). Cryst. Growth Des. 10, 492-494.]); Zhou et al. (2011[Zhou, R. S., Song, J. F., Li, Y. B., Xu, C. Y. & Yang, X. F. (2011). Z. Anorg. Allg. Chem. 637, 251-256.]). For the synthesis of the title compound, see: Lebedev et al. (2007[Lebedev, A. V., Lebedev, A. B., Sheludyakov, V. D., Kovaleva, E. A., Ustinova, O. L. & Shatunov, V. V. (2007). Russ. J. Gen. Chem. 77, 949-953.]).

[Scheme 1]

Experimental

Crystal data

  • C11H9N3O4

  • Mr = 247.21

  • Monoclinic, P 21 /c

  • a = 5.4407 (17) Å

  • b = 8.634 (3) Å

  • c = 22.317 (7) Å

  • β = 96.327 (4)°

  • V = 1042.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 298 K

  • 0.20 × 0.15 × 0.12 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.985

  • 4932 measured reflections

  • 1816 independent reflections

  • 1315 reflections with I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.167

  • S = 1.10

  • 1816 reflections

  • 165 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.86 1.91 2.764 (3) 174
O3—H3⋯O2 0.82 1.64 2.461 (3) 176
C7—H7⋯O1i 0.93 2.24 3.145 (4) 165
C8—H8⋯O3ii 0.93 2.58 3.363 (4) 142
C10—H10⋯O4iii 0.93 2.32 3.172 (4) 152
C11—H11C⋯O4iii 0.96 2.35 3.223 (4) 150
Symmetry codes: (i) -x, -y+1, -z+2; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055644/cv5222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055644/cv5222Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055644/cv5222Isup3.cml

checkCIF report


Comment top

The construction of metal complexes based on 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acid has attracted much attention due to their intriguing topologies and potential applications in many fields (Sun et al., 2006; Li et al., 2009a,b; Jing et al., 2010a,b; Zhou et al., 2011). In the search for new 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acids, the title compound, (I), has been synthesized. Herewith we report its crystal structure.

In (I) (Fig. 1), the C1-containing carboxyl group is deprotonated and forms an intramolecular hydrogen bond with the neighboring C4-containing carboxyl group. The dihedral angle formed by the imidazole and pyridyl rings is 2.60 (2) °. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2). Weak intermolecular C—H···O interactions (Table 1) consolidate further the crystal packing.

Related literature top

For the use and related structures of the multifunctional connector 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acid in coordination chemistry, see: Sun et al. (2006); Li et al. (2009a,b); Jing et al. (2010a,b); Zhou et al. (2011). For the synthesis of the title compound, see: Lebedev et al. (2007).

Experimental top

The title compound was synthesized according to the method reported in the literature (Lebedev et al., 2007). Light yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetonitrile solution of the compound.

Refinement top

All H atoms were placed in calculated positions (C—H = 0.93—0.96 Å, N—H = 0.86 Å and O—H = 0.82 Å) and refined as riding. For those bound to Caryl and N, Uiso(H) = 1.2 Ueq(C, N), while for those bound to Cmethyl and O, Uiso(H) = 1.5 Ueq(C, O).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The hydrogen-bonded (dashed lines) dimer in (I). H atoms not included in hydrogen bonding have been omitted for clarity.
4-carboxy-2-(1-methylpyridin-1-ium-4-yl)-1H-imidazole-5-carboxylate top
Crystal data top
C11H9N3O4F(000) = 512
Mr = 247.21Dx = 1.576 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1531 reflections
a = 5.4407 (17) Åθ = 2.5–26.9°
b = 8.634 (3) ŵ = 0.12 mm−1
c = 22.317 (7) ÅT = 298 K
β = 96.327 (4)°Block, light yellow
V = 1042.0 (6) Å30.20 × 0.15 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		1816 independent reflections
Radiation source: fine-focus sealed tube1315 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −6→6
Tmin = 0.976, Tmax = 0.985k = −10→9
4932 measured reflectionsl = −26→24
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0889P)2 + 0.001P]
where P = (Fo2 + 2Fc2)/3
1816 reflections(Δ/σ)max = 0.001
165 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C11H9N3O4V = 1042.0 (6) Å3
Mr = 247.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.4407 (17) ŵ = 0.12 mm−1
b = 8.634 (3) ÅT = 298 K
c = 22.317 (7) Å0.20 × 0.15 × 0.12 mm
β = 96.327 (4)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		1816 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1315 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.985Rint = 0.039
4932 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.10Δρmax = 0.23 e Å−3
1816 reflectionsΔρmin = −0.26 e Å−3
165 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
C10.0755 (6)0.6050 (4)1.10251 (13)0.0317 (8)
C20.2747 (5)0.6905 (3)1.07599 (12)0.0267 (7)
C30.4543 (5)0.7976 (3)1.09778 (12)0.0274 (7)
C40.4977 (6)0.8681 (3)1.15866 (13)0.0322 (8)
C50.5063 (5)0.7576 (3)1.00524 (12)0.0273 (7)
C60.6061 (5)0.7649 (3)0.94726 (12)0.0280 (7)
C70.5034 (6)0.6830 (3)0.89683 (13)0.0317 (8)
H70.36590.62030.89920.038*
C80.6059 (6)0.6954 (4)0.84385 (13)0.0342 (8)
H80.53700.64070.81020.041*
C90.8120 (6)0.8566 (3)0.94116 (13)0.0318 (8)
H90.88440.91260.97410.038*
C100.9089 (6)0.8656 (4)0.88748 (13)0.0341 (8)
H101.04690.92710.88400.041*
C110.9080 (7)0.7973 (5)0.78104 (14)0.0559 (11)
H11A0.80380.86260.75430.084*
H11B0.91610.69600.76360.084*
H11C1.07110.84090.78730.084*
N10.3130 (4)0.6680 (3)1.01751 (10)0.0280 (6)
H10.22890.60730.99250.034*
N20.5960 (5)0.8392 (3)1.05351 (10)0.0299 (6)
N30.8048 (5)0.7854 (3)0.83951 (10)0.0322 (7)
O1−0.0546 (4)0.5157 (3)1.06919 (9)0.0433 (7)
O20.0558 (5)0.6265 (3)1.15773 (9)0.0483 (7)
O30.3582 (5)0.8213 (3)1.19912 (9)0.0486 (7)
H30.26300.75431.18450.073*
O40.6553 (4)0.9671 (3)1.17050 (9)0.0454 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0347 (19)0.0341 (18)0.0278 (16)−0.0051 (15)0.0098 (13)0.0006 (14)
C20.0324 (18)0.0282 (17)0.0203 (15)0.0011 (13)0.0072 (12)−0.0009 (12)
C30.0334 (18)0.0273 (16)0.0222 (15)−0.0023 (13)0.0057 (13)−0.0002 (12)
C40.0350 (19)0.0365 (19)0.0255 (16)−0.0037 (15)0.0053 (14)−0.0007 (14)
C50.0307 (17)0.0282 (16)0.0238 (15)−0.0023 (13)0.0058 (12)0.0019 (12)
C60.0310 (17)0.0283 (16)0.0253 (16)0.0017 (14)0.0046 (13)0.0022 (13)
C70.0342 (18)0.0344 (18)0.0275 (16)−0.0071 (14)0.0082 (13)0.0003 (13)
C80.0351 (19)0.0407 (19)0.0269 (16)−0.0054 (15)0.0042 (14)−0.0034 (14)
C90.0350 (19)0.0355 (18)0.0260 (16)−0.0074 (14)0.0076 (13)−0.0052 (13)
C100.0321 (19)0.0382 (19)0.0324 (17)−0.0081 (14)0.0058 (14)−0.0021 (14)
C110.061 (3)0.080 (3)0.0312 (19)−0.022 (2)0.0210 (17)−0.0111 (18)
N10.0318 (15)0.0298 (14)0.0232 (13)−0.0060 (11)0.0059 (11)−0.0024 (10)
N20.0347 (15)0.0308 (14)0.0250 (13)−0.0035 (11)0.0075 (11)0.0020 (11)
N30.0327 (16)0.0404 (16)0.0248 (13)−0.0042 (12)0.0088 (11)−0.0014 (11)
O10.0483 (15)0.0477 (14)0.0358 (13)−0.0221 (11)0.0127 (11)−0.0106 (11)
O20.0573 (16)0.0652 (17)0.0256 (12)−0.0240 (13)0.0190 (10)−0.0065 (11)
O30.0550 (16)0.0661 (17)0.0265 (12)−0.0264 (13)0.0135 (11)−0.0101 (11)
O40.0523 (16)0.0483 (14)0.0358 (13)−0.0199 (12)0.0062 (11)−0.0091 (11)
Geometric parameters (Å, º) top
C1—O11.238 (3)C7—C81.366 (4)
C1—O21.262 (4)C7—H70.9300
C1—C21.487 (4)C8—N31.344 (4)
C2—N11.358 (3)C8—H80.9300
C2—C31.393 (4)C9—C101.363 (4)
C3—N21.367 (4)C9—H90.9300
C3—C41.484 (4)C10—N31.346 (4)
C4—O41.219 (3)C10—H100.9300
C4—O31.306 (4)C11—N31.480 (4)
C5—N21.334 (4)C11—H11A0.9600
C5—N11.358 (4)C11—H11B0.9600
C5—C61.459 (4)C11—H11C0.9600
C6—C91.391 (4)N1—H10.8600
C6—C71.393 (4)O3—H30.8200
O1—C1—O2125.0 (3)N3—C8—H8119.5
O1—C1—C2117.6 (3)C7—C8—H8119.5
O2—C1—C2117.4 (3)C10—C9—C6120.8 (3)
N1—C2—C3104.7 (3)C10—C9—H9119.6
N1—C2—C1120.5 (2)C6—C9—H9119.6
C3—C2—C1134.8 (3)N3—C10—C9120.0 (3)
N2—C3—C2110.6 (2)N3—C10—H10120.0
N2—C3—C4120.6 (3)C9—C10—H10120.0
C2—C3—C4128.8 (3)N3—C11—H11A109.5
O4—C4—O3121.0 (3)N3—C11—H11B109.5
O4—C4—C3121.5 (3)H11A—C11—H11B109.5
O3—C4—C3117.4 (3)N3—C11—H11C109.5
N2—C5—N1111.1 (3)H11A—C11—H11C109.5
N2—C5—C6123.7 (3)H11B—C11—H11C109.5
N1—C5—C6125.2 (3)C5—N1—C2108.5 (2)
C9—C6—C7117.7 (3)C5—N1—H1125.8
C9—C6—C5119.6 (3)C2—N1—H1125.8
C7—C6—C5122.7 (3)C5—N2—C3105.0 (2)
C8—C7—C6119.6 (3)C8—N3—C10120.7 (3)
C8—C7—H7120.2C8—N3—C11119.3 (3)
C6—C7—H7120.2C10—N3—C11119.9 (3)
N3—C8—C7121.1 (3)C4—O3—H3109.5
O1—C1—C2—N1−1.2 (4)C5—C6—C7—C8179.8 (3)
O2—C1—C2—N1177.3 (3)C6—C7—C8—N30.0 (5)
O1—C1—C2—C3−179.9 (3)C7—C6—C9—C100.0 (4)
O2—C1—C2—C3−1.5 (5)C5—C6—C9—C10−180.0 (3)
N1—C2—C3—N20.4 (3)C6—C9—C10—N30.2 (5)
C1—C2—C3—N2179.2 (3)N2—C5—N1—C2−0.4 (3)
N1—C2—C3—C4178.5 (3)C6—C5—N1—C2179.4 (3)
C1—C2—C3—C4−2.6 (5)C3—C2—N1—C50.0 (3)
N2—C3—C4—O41.9 (4)C1—C2—N1—C5−179.1 (2)
C2—C3—C4—O4−176.1 (3)N1—C5—N2—C30.6 (3)
N2—C3—C4—O3−178.9 (3)C6—C5—N2—C3−179.2 (3)
C2—C3—C4—O33.1 (5)C2—C3—N2—C5−0.6 (3)
N2—C5—C6—C92.5 (4)C4—C3—N2—C5−178.9 (3)
N1—C5—C6—C9−177.3 (3)C7—C8—N3—C100.2 (5)
N2—C5—C6—C7−177.5 (3)C7—C8—N3—C11−179.2 (3)
N1—C5—C6—C72.7 (5)C9—C10—N3—C8−0.3 (4)
C9—C6—C7—C8−0.1 (4)C9—C10—N3—C11179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.912.764 (3)174
O3—H3···O20.821.642.461 (3)176
C7—H7···O1i0.932.243.145 (4)165
C8—H8···O3ii0.932.583.363 (4)142
C10—H10···O4iii0.932.323.172 (4)152
C11—H11C···O4iii0.962.353.223 (4)150
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formulaC11H9N3O4
Mr247.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)5.4407 (17), 8.634 (3), 22.317 (7)
β (°) 96.327 (4)
V (Å3)1042.0 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.20 × 0.15 × 0.12
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.976, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections		4932, 1816, 1315
Rint0.039
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.167, 1.10
No. of reflections1816
No. of parameters165
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.912.764 (3)174.4
O3—H3···O20.821.642.461 (3)175.7
C7—H7···O1i0.932.243.145 (4)164.9
C8—H8···O3ii0.932.583.363 (4)141.8
C10—H10···O4iii0.932.323.172 (4)152.4
C11—H11C···O4iii0.962.353.223 (4)150.2
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x+2, −y+2, −z+2.
 

Acknowledgements

This work was supported financially by the Program for Young Teachers Scientific Research in Qiqihar University (PYTSRQU) (grant No. 2011k-M07).

References

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ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o358
doi:10.1107/S1600536811055644
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