Zwitterionic 4-carb-oxy-2-(1-methyl-pyridin-1-ium-4-yl)-1H-imidazole-5-carboxyl-ate.

In the title zwitterionic mol-ecule, C(11)H(9)N(3)O(4), the imidazole and pyridine rings form a dihedral angle of 2.60 (2)°. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into inversion dimers. Weak inter-molecular C-H⋯O inter-actions 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 ▶); Li et al. (2009 ▶); Jing et al. (2010 ▶); Zhou et al. (2011 ▶). For the synthesis of the title compound, see: Lebedev et al. (2007 ▶).

Experimental

Crystal data

C11H9N3O4

M = 247.21

Monoclinic,

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 ▶) T min = 0.976, T max = 0.985

4932 measured reflections

1816 independent reflections

1315 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055644/cv5222sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811055644/cv5222Isup3.cml

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

C11H9N3O4	F(000) = 512
Mr = 247.21	Dx = 1.576 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1531 reflections
a = 5.4407 (17) Å	θ = 2.5–26.9°
b = 8.634 (3) Å	µ = 0.12 mm−1
c = 22.317 (7) Å	T = 298 K
β = 96.327 (4)°	Block, light yellow
V = 1042.0 (6) Å3	0.20 × 0.15 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1816 independent reflections
Radiation source: fine-focus sealed tube	1315 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.976, Tmax = 0.985	k = −10→9
4932 measured reflections	l = −26→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-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 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0755 (6)	0.6050 (4)	1.10251 (13)	0.0317 (8)
C2	0.2747 (5)	0.6905 (3)	1.07599 (12)	0.0267 (7)
C3	0.4543 (5)	0.7976 (3)	1.09778 (12)	0.0274 (7)
C4	0.4977 (6)	0.8681 (3)	1.15866 (13)	0.0322 (8)
C5	0.5063 (5)	0.7576 (3)	1.00524 (12)	0.0273 (7)
C6	0.6061 (5)	0.7649 (3)	0.94726 (12)	0.0280 (7)
C7	0.5034 (6)	0.6830 (3)	0.89683 (13)	0.0317 (8)
H7	0.3659	0.6203	0.8992	0.038*
C8	0.6059 (6)	0.6954 (4)	0.84385 (13)	0.0342 (8)
H8	0.5370	0.6407	0.8102	0.041*
C9	0.8120 (6)	0.8566 (3)	0.94116 (13)	0.0318 (8)
H9	0.8844	0.9126	0.9741	0.038*
C10	0.9089 (6)	0.8656 (4)	0.88748 (13)	0.0341 (8)
H10	1.0469	0.9271	0.8840	0.041*
C11	0.9080 (7)	0.7973 (5)	0.78104 (14)	0.0559 (11)
H11A	0.8038	0.8626	0.7543	0.084*
H11B	0.9161	0.6960	0.7636	0.084*
H11C	1.0711	0.8409	0.7873	0.084*
N1	0.3130 (4)	0.6680 (3)	1.01751 (10)	0.0280 (6)
H1	0.2289	0.6073	0.9925	0.034*
N2	0.5960 (5)	0.8392 (3)	1.05351 (10)	0.0299 (6)
N3	0.8048 (5)	0.7854 (3)	0.83951 (10)	0.0322 (7)
O1	−0.0546 (4)	0.5157 (3)	1.06919 (9)	0.0433 (7)
O2	0.0558 (5)	0.6265 (3)	1.15773 (9)	0.0483 (7)
O3	0.3582 (5)	0.8213 (3)	1.19912 (9)	0.0486 (7)
H3	0.2630	0.7543	1.1845	0.073*
O4	0.6553 (4)	0.9671 (3)	1.17050 (9)	0.0454 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0347 (19)	0.0341 (18)	0.0278 (16)	−0.0051 (15)	0.0098 (13)	0.0006 (14)
C2	0.0324 (18)	0.0282 (17)	0.0203 (15)	0.0011 (13)	0.0072 (12)	−0.0009 (12)
C3	0.0334 (18)	0.0273 (16)	0.0222 (15)	−0.0023 (13)	0.0057 (13)	−0.0002 (12)
C4	0.0350 (19)	0.0365 (19)	0.0255 (16)	−0.0037 (15)	0.0053 (14)	−0.0007 (14)
C5	0.0307 (17)	0.0282 (16)	0.0238 (15)	−0.0023 (13)	0.0058 (12)	0.0019 (12)
C6	0.0310 (17)	0.0283 (16)	0.0253 (16)	0.0017 (14)	0.0046 (13)	0.0022 (13)
C7	0.0342 (18)	0.0344 (18)	0.0275 (16)	−0.0071 (14)	0.0082 (13)	0.0003 (13)
C8	0.0351 (19)	0.0407 (19)	0.0269 (16)	−0.0054 (15)	0.0042 (14)	−0.0034 (14)
C9	0.0350 (19)	0.0355 (18)	0.0260 (16)	−0.0074 (14)	0.0076 (13)	−0.0052 (13)
C10	0.0321 (19)	0.0382 (19)	0.0324 (17)	−0.0081 (14)	0.0058 (14)	−0.0021 (14)
C11	0.061 (3)	0.080 (3)	0.0312 (19)	−0.022 (2)	0.0210 (17)	−0.0111 (18)
N1	0.0318 (15)	0.0298 (14)	0.0232 (13)	−0.0060 (11)	0.0059 (11)	−0.0024 (10)
N2	0.0347 (15)	0.0308 (14)	0.0250 (13)	−0.0035 (11)	0.0075 (11)	0.0020 (11)
N3	0.0327 (16)	0.0404 (16)	0.0248 (13)	−0.0042 (12)	0.0088 (11)	−0.0014 (11)
O1	0.0483 (15)	0.0477 (14)	0.0358 (13)	−0.0221 (11)	0.0127 (11)	−0.0106 (11)
O2	0.0573 (16)	0.0652 (17)	0.0256 (12)	−0.0240 (13)	0.0190 (10)	−0.0065 (11)
O3	0.0550 (16)	0.0661 (17)	0.0265 (12)	−0.0264 (13)	0.0135 (11)	−0.0101 (11)
O4	0.0523 (16)	0.0483 (14)	0.0358 (13)	−0.0199 (12)	0.0062 (11)	−0.0091 (11)

C1—O1	1.238 (3)	C7—C8	1.366 (4)
C1—O2	1.262 (4)	C7—H7	0.9300
C1—C2	1.487 (4)	C8—N3	1.344 (4)
C2—N1	1.358 (3)	C8—H8	0.9300
C2—C3	1.393 (4)	C9—C10	1.363 (4)
C3—N2	1.367 (4)	C9—H9	0.9300
C3—C4	1.484 (4)	C10—N3	1.346 (4)
C4—O4	1.219 (3)	C10—H10	0.9300
C4—O3	1.306 (4)	C11—N3	1.480 (4)
C5—N2	1.334 (4)	C11—H11A	0.9600
C5—N1	1.358 (4)	C11—H11B	0.9600
C5—C6	1.459 (4)	C11—H11C	0.9600
C6—C9	1.391 (4)	N1—H1	0.8600
C6—C7	1.393 (4)	O3—H3	0.8200
O1—C1—O2	125.0 (3)	N3—C8—H8	119.5
O1—C1—C2	117.6 (3)	C7—C8—H8	119.5
O2—C1—C2	117.4 (3)	C10—C9—C6	120.8 (3)
N1—C2—C3	104.7 (3)	C10—C9—H9	119.6
N1—C2—C1	120.5 (2)	C6—C9—H9	119.6
C3—C2—C1	134.8 (3)	N3—C10—C9	120.0 (3)
N2—C3—C2	110.6 (2)	N3—C10—H10	120.0
N2—C3—C4	120.6 (3)	C9—C10—H10	120.0
C2—C3—C4	128.8 (3)	N3—C11—H11A	109.5
O4—C4—O3	121.0 (3)	N3—C11—H11B	109.5
O4—C4—C3	121.5 (3)	H11A—C11—H11B	109.5
O3—C4—C3	117.4 (3)	N3—C11—H11C	109.5
N2—C5—N1	111.1 (3)	H11A—C11—H11C	109.5
N2—C5—C6	123.7 (3)	H11B—C11—H11C	109.5
N1—C5—C6	125.2 (3)	C5—N1—C2	108.5 (2)
C9—C6—C7	117.7 (3)	C5—N1—H1	125.8
C9—C6—C5	119.6 (3)	C2—N1—H1	125.8
C7—C6—C5	122.7 (3)	C5—N2—C3	105.0 (2)
C8—C7—C6	119.6 (3)	C8—N3—C10	120.7 (3)
C8—C7—H7	120.2	C8—N3—C11	119.3 (3)
C6—C7—H7	120.2	C10—N3—C11	119.9 (3)
N3—C8—C7	121.1 (3)	C4—O3—H3	109.5
O1—C1—C2—N1	−1.2 (4)	C5—C6—C7—C8	179.8 (3)
O2—C1—C2—N1	177.3 (3)	C6—C7—C8—N3	0.0 (5)
O1—C1—C2—C3	−179.9 (3)	C7—C6—C9—C10	0.0 (4)
O2—C1—C2—C3	−1.5 (5)	C5—C6—C9—C10	−180.0 (3)
N1—C2—C3—N2	0.4 (3)	C6—C9—C10—N3	0.2 (5)
C1—C2—C3—N2	179.2 (3)	N2—C5—N1—C2	−0.4 (3)
N1—C2—C3—C4	178.5 (3)	C6—C5—N1—C2	179.4 (3)
C1—C2—C3—C4	−2.6 (5)	C3—C2—N1—C5	0.0 (3)
N2—C3—C4—O4	1.9 (4)	C1—C2—N1—C5	−179.1 (2)
C2—C3—C4—O4	−176.1 (3)	N1—C5—N2—C3	0.6 (3)
N2—C3—C4—O3	−178.9 (3)	C6—C5—N2—C3	−179.2 (3)
C2—C3—C4—O3	3.1 (5)	C2—C3—N2—C5	−0.6 (3)
N2—C5—C6—C9	2.5 (4)	C4—C3—N2—C5	−178.9 (3)
N1—C5—C6—C9	−177.3 (3)	C7—C8—N3—C10	0.2 (5)
N2—C5—C6—C7	−177.5 (3)	C7—C8—N3—C11	−179.2 (3)
N1—C5—C6—C7	2.7 (5)	C9—C10—N3—C8	−0.3 (4)
C9—C6—C7—C8	−0.1 (4)	C9—C10—N3—C11	179.0 (3)

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

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) ; (ii) ; (iii) .