2-(Carb-oxy-meth-yl)imidazo[1,2-a]pyridin-1-ium chloride.

In the crystal structure of the title salt, C(9)H(9)N(2)O(2) (+)·Cl(-), the cations and anions are linked into chains parallel to [021] by O-H⋯Cl and N-H⋯Cl hydrogen bonds.

Related literature

For the diversity of structures and the applications of compounds with an imidazole moiety, see: Catalano & Etogo (2007 ▶); Feng et al. (2012 ▶); Keppler et al. (1987 ▶); Poul et al. (2007 ▶); Saha et al. (2012 ▶); Samantaray et al. (2007 ▶); Takagaki et al. (2012 ▶).

Experimental

Crystal data

C9H9N2O2 +·Cl−

M = 212.63

Monoclinic,

a = 5.4032 (8) Å

b = 14.722 (2) Å

c = 12.1055 (18) Å

β = 96.182 (4)°

V = 957.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 293 K

0.25 × 0.15 × 0.12 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.913, T max = 0.957

7948 measured reflections

1689 independent reflections

1417 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.083

S = 1.02

1689 reflections

134 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051549/hp2052sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051549/hp2052Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051549/hp2052Isup3.cml

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

C9H9N2O2+·Cl−	F(000) = 440
Mr = 212.63	Dx = 1.475 Mg m−3Dm = 1.475 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9784 reflections
a = 5.4032 (8) Å	θ = 3.2–25.0°
b = 14.722 (2) Å	µ = 0.37 mm−1
c = 12.1055 (18) Å	T = 293 K
β = 96.182 (4)°	Block, yellow
V = 957.3 (2) Å3	0.25 × 0.15 × 0.12 mm
Z = 4

Rigaku Mercury diffractometer	1689 independent reflections
Radiation source: fine-focus sealed tube	1417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
/w scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −6→6
Tmin = 0.913, Tmax = 0.957	k = −17→17
7948 measured reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0102P)2 + 1.0216P] where P = (Fo2 + 2Fc2)/3
1689 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 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
Cl1	0.99075 (13)	0.33311 (5)	0.93211 (6)	0.0507 (2)
C1	0.3725 (4)	0.61391 (17)	0.6832 (2)	0.0372 (6)
C6	0.6807 (5)	0.57805 (17)	0.5799 (2)	0.0396 (6)
H6	0.8196	0.5503	0.5556	0.048*
O1	0.7448 (4)	0.72008 (14)	0.26206 (16)	0.0559 (6)
H1	0.8352	0.6986	0.2184	0.084*
O2	0.9053 (3)	0.60844 (14)	0.37360 (15)	0.0540 (5)
N1	0.5729 (4)	0.55760 (14)	0.67658 (17)	0.0363 (5)
C5	0.6379 (5)	0.49364 (18)	0.7568 (2)	0.0431 (7)
H2	0.7747	0.4561	0.7521	0.052*
C4	0.4994 (5)	0.48630 (19)	0.8428 (2)	0.0482 (7)
H3	0.5406	0.4428	0.8974	0.058*
C3	0.2926 (5)	0.5438 (2)	0.8513 (2)	0.0496 (7)
H4	0.1992	0.5377	0.9110	0.060*
C2	0.2295 (5)	0.60797 (19)	0.7725 (2)	0.0451 (7)
H5	0.0954	0.6467	0.7779	0.054*
N2	0.3549 (4)	0.66686 (16)	0.59268 (18)	0.0402 (5)
C7	0.5447 (5)	0.64601 (17)	0.5281 (2)	0.0374 (6)
C8	0.5594 (5)	0.69786 (18)	0.4237 (2)	0.0451 (7)
H8A	0.5862	0.7613	0.4428	0.054*
H8B	0.3994	0.6935	0.3792	0.054*
C9	0.7576 (5)	0.66897 (19)	0.3528 (2)	0.0419 (6)
H2A	0.251 (6)	0.714 (2)	0.581 (2)	0.067 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0547 (4)	0.0434 (4)	0.0564 (4)	−0.0043 (3)	0.0173 (3)	0.0008 (3)
C1	0.0329 (14)	0.0375 (15)	0.0410 (15)	−0.0032 (11)	0.0026 (12)	−0.0069 (12)
C6	0.0347 (14)	0.0426 (16)	0.0429 (15)	0.0031 (12)	0.0099 (12)	−0.0034 (12)
O1	0.0640 (14)	0.0566 (13)	0.0500 (12)	0.0101 (10)	0.0193 (10)	0.0099 (11)
O2	0.0505 (12)	0.0654 (14)	0.0475 (11)	0.0186 (11)	0.0110 (10)	0.0049 (10)
N1	0.0337 (11)	0.0358 (12)	0.0393 (12)	−0.0016 (10)	0.0035 (10)	−0.0030 (10)
C5	0.0395 (15)	0.0441 (16)	0.0448 (16)	0.0022 (12)	0.0002 (13)	0.0016 (13)
C4	0.0530 (18)	0.0477 (17)	0.0430 (16)	−0.0026 (14)	0.0010 (14)	0.0028 (13)
C3	0.0514 (17)	0.0566 (19)	0.0422 (16)	−0.0097 (15)	0.0113 (14)	−0.0047 (14)
C2	0.0400 (15)	0.0484 (17)	0.0484 (16)	0.0007 (13)	0.0115 (13)	−0.0100 (14)
N2	0.0363 (12)	0.0401 (13)	0.0446 (13)	0.0055 (11)	0.0066 (10)	−0.0019 (11)
C7	0.0346 (13)	0.0371 (15)	0.0408 (14)	−0.0023 (11)	0.0064 (12)	−0.0061 (12)
C8	0.0454 (16)	0.0442 (16)	0.0459 (16)	0.0053 (13)	0.0064 (13)	0.0007 (13)
C9	0.0410 (15)	0.0432 (16)	0.0412 (15)	−0.0040 (13)	0.0033 (12)	−0.0036 (13)

C1—N2	1.340 (3)	C4—C3	1.414 (4)
C1—N1	1.373 (3)	C4—H3	0.9300
C1—C2	1.398 (4)	C3—C2	1.359 (4)
C6—C7	1.354 (3)	C3—H4	0.9300
C6—N1	1.395 (3)	C2—H5	0.9300
C6—H6	0.9300	N2—C7	1.389 (3)
O1—C9	1.327 (3)	N2—H2A	0.89 (3)
O1—H1	0.8200	C7—C8	1.487 (4)
O2—C9	1.205 (3)	C8—C9	1.503 (4)
N1—C5	1.371 (3)	C8—H8A	0.9700
C5—C4	1.351 (4)	C8—H8B	0.9700
C5—H2	0.9300
N2—C1—N1	106.9 (2)	C3—C2—C1	117.9 (3)
N2—C1—C2	132.3 (2)	C3—C2—H5	121.0
N1—C1—C2	120.8 (2)	C1—C2—H5	121.0
C7—C6—N1	107.0 (2)	C1—N2—C7	109.9 (2)
C7—C6—H6	126.5	C1—N2—H2A	124 (2)
N1—C6—H6	126.5	C7—N2—H2A	125 (2)
C9—O1—H1	109.5	C6—C7—N2	107.4 (2)
C5—N1—C1	121.1 (2)	C6—C7—C8	134.2 (2)
C5—N1—C6	130.1 (2)	N2—C7—C8	118.4 (2)
C1—N1—C6	108.8 (2)	C7—C8—C9	116.5 (2)
C4—C5—N1	118.7 (3)	C7—C8—H8A	108.2
C4—C5—H2	120.7	C9—C8—H8A	108.2
N1—C5—H2	120.7	C7—C8—H8B	108.2
C5—C4—C3	121.0 (3)	C9—C8—H8B	108.2
C5—C4—H3	119.5	H8A—C8—H8B	107.3
C3—C4—H3	119.5	O2—C9—O1	124.5 (2)
C2—C3—C4	120.4 (3)	O2—C9—C8	125.9 (3)
C2—C3—H4	119.8	O1—C9—C8	109.6 (2)
C4—C3—H4	119.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1i	0.82	2.19	2.984 (2)	163
N2—H2A···Cl1ii	0.89 (3)	2.18 (3)	3.074 (2)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1i	0.82	2.19	2.984 (2)	163
N2—H2A⋯Cl1ii	0.89 (3)	2.18 (3)	3.074 (2)	175 (3)

Symmetry codes: (i) ; (ii) .