1-Methyl-3-(4-chloro-benzo-yl)imidazo[1,2-a]pyridin-1-ium-2-olate.

In the mol-ecule of the title compound, C(15)H(11)ClN(2)O(2), the nine-membered heterobicycle is approximately planar [largest deviation from least-squares plane = 0.012 (2) Å] and forms a dihedral angle of 51.14 (8)° with the plane of the 4-chloro-phenyl group. There is a non-classical intra-molecular hydrogen bond between the pyridine α-H atom and the O atom of the benzoyl group. The crystal structure is stabilized by weak C-H⋯O and C-H⋯Cl inter-actions involving the 'olate' O atom and the Cl atom attached to the benzoyl group as acceptors.

Related literature

For related structures, see: Friedman et al. (1978 ▶); Rybakov et al. (1999 ▶, 2000a ▶,b ▶, 2001 ▶, 2002 ▶). For the synthesis of 1-methyl-2-oxo-2,3-dihydro­imidazopyridinium perchlorate, see: Sych & Gorb (1976 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C15H11ClN2O2

M = 286.71

Monoclinic,

a = 8.190 (8) Å

b = 13.914 (3) Å

c = 11.675 (4) Å

β = 102.38 (2)°

V = 1299.5 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 295 K

0.30 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

2675 measured reflections

2546 independent reflections

1486 reflections with I > 2σ(I)

R int = 0.042

1 standard reflections every 200 reflections intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.107

S = 0.94

2546 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1994) ▶; cell refinement: CAD-4 Software ▶; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039614/yk2022sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039614/yk2022Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039614/yk2022Isup3.cml

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

C15H11ClN2O2	F(000) = 592
Mr = 286.71	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Melting point = 479–481 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.190 (8) Å	Cell parameters from 25 reflections
b = 13.914 (3) Å	θ = 13.0–14.8°
c = 11.675 (4) Å	µ = 0.30 mm−1
β = 102.38 (2)°	T = 295 K
V = 1299.5 (14) Å3	Prism, green
Z = 4	0.30 × 0.30 × 0.30 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.3°
graphite	h = −10→9
non–profiled ω scans	k = 0→17
2675 measured reflections	l = 0→14
2546 independent reflections	1 standard reflections every 200 reflections
1486 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0433P)2] where P = (Fo2 + 2Fc2)/3
2546 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.0863 (3)	0.54749 (15)	0.22101 (19)	0.0505 (6)
C2	0.1226 (3)	0.45544 (18)	0.1820 (2)	0.0449 (6)
O2	0.0815 (2)	0.38150 (13)	0.22548 (16)	0.0594 (5)
C3	0.2076 (3)	0.47398 (16)	0.0895 (2)	0.0424 (6)
N4	0.2102 (2)	0.57470 (13)	0.07555 (17)	0.0416 (5)
C5	0.2755 (3)	0.62878 (19)	−0.0013 (2)	0.0521 (7)
H5	0.3244	0.5997	−0.0574	0.063*
C6	0.2675 (4)	0.7264 (2)	0.0060 (3)	0.0646 (9)
H6	0.3118	0.7641	−0.0457	0.078*
C7	0.1947 (4)	0.7704 (2)	0.0887 (3)	0.0690 (9)
H7	0.1903	0.8371	0.0920	0.083*
C8	0.1292 (4)	0.71635 (19)	0.1653 (3)	0.0609 (8)
H8	0.0801	0.7453	0.2213	0.073*
C9	0.1377 (3)	0.61773 (18)	0.1577 (2)	0.0469 (6)
C11	−0.0063 (4)	0.5623 (2)	0.3124 (3)	0.0725 (9)
H11A	0.0696	0.5797	0.3840	0.109*
H11B	−0.0636	0.5041	0.3240	0.109*
H11C	−0.0863	0.6129	0.2895	0.109*
C30	0.2748 (3)	0.40950 (17)	0.0162 (2)	0.0459 (6)
O30	0.3115 (3)	0.43543 (13)	−0.07607 (15)	0.0659 (6)
C31	0.3064 (3)	0.30759 (17)	0.0552 (2)	0.0390 (6)
C32	0.3762 (3)	0.28280 (17)	0.1699 (2)	0.0451 (6)
H32	0.3955	0.3304	0.2271	0.054*
C33	0.4177 (3)	0.18918 (18)	0.2012 (2)	0.0463 (6)
H33	0.4654	0.1733	0.2785	0.056*
C34	0.3869 (3)	0.11962 (17)	0.1154 (2)	0.0450 (6)
Cl34	0.43791 (11)	0.00078 (5)	0.15427 (8)	0.0725 (3)
C35	0.3144 (3)	0.14142 (17)	0.0010 (2)	0.0478 (7)
H35	0.2914	0.0931	−0.0552	0.057*
C36	0.2766 (3)	0.23515 (18)	−0.0291 (2)	0.0460 (7)
H36	0.2305	0.2507	−0.1068	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.0450 (14)	0.0641 (14)	0.0448 (14)	0.0060 (11)	0.0150 (12)	−0.0039 (12)
C2	0.0378 (16)	0.0555 (15)	0.0389 (15)	0.0004 (12)	0.0023 (13)	−0.0033 (13)
O2	0.0603 (13)	0.0647 (12)	0.0568 (13)	−0.0035 (10)	0.0208 (11)	0.0127 (10)
C3	0.0415 (15)	0.0452 (13)	0.0396 (15)	0.0000 (11)	0.0071 (13)	0.0030 (11)
N4	0.0339 (12)	0.0468 (11)	0.0409 (12)	0.0017 (9)	0.0012 (10)	0.0011 (10)
C5	0.0418 (17)	0.0627 (17)	0.0506 (17)	0.0017 (13)	0.0071 (14)	0.0112 (14)
C6	0.050 (2)	0.0561 (17)	0.082 (2)	−0.0012 (14)	0.0015 (18)	0.0165 (16)
C7	0.056 (2)	0.0515 (17)	0.089 (3)	0.0079 (15)	−0.0079 (19)	−0.0010 (18)
C8	0.0476 (19)	0.0582 (17)	0.072 (2)	0.0084 (14)	0.0022 (17)	−0.0111 (16)
C9	0.0372 (16)	0.0568 (15)	0.0460 (17)	0.0101 (12)	0.0071 (13)	−0.0063 (13)
C11	0.069 (2)	0.098 (2)	0.057 (2)	0.0132 (18)	0.0286 (18)	−0.0073 (18)
C30	0.0430 (16)	0.0554 (16)	0.0382 (16)	−0.0002 (12)	0.0060 (13)	0.0004 (12)
O30	0.0985 (17)	0.0675 (12)	0.0383 (11)	0.0132 (11)	0.0289 (12)	0.0086 (10)
C31	0.0336 (14)	0.0519 (14)	0.0291 (14)	0.0011 (11)	0.0012 (11)	−0.0001 (11)
C32	0.0471 (17)	0.0500 (14)	0.0359 (15)	−0.0021 (12)	0.0037 (13)	−0.0056 (12)
C33	0.0409 (16)	0.0557 (15)	0.0392 (15)	0.0044 (12)	0.0019 (12)	0.0035 (13)
C34	0.0362 (15)	0.0475 (14)	0.0536 (17)	0.0070 (11)	0.0149 (14)	0.0050 (13)
Cl34	0.0791 (6)	0.0543 (4)	0.0870 (7)	0.0176 (4)	0.0246 (5)	0.0101 (4)
C35	0.0469 (17)	0.0510 (15)	0.0434 (16)	0.0013 (12)	0.0055 (13)	−0.0132 (13)
C36	0.0412 (16)	0.0596 (16)	0.0343 (15)	0.0038 (12)	0.0016 (13)	−0.0043 (12)

Cl34—C34	1.742 (2)	C5—H5	0.9300
N4—C5	1.365 (3)	C30—O30	1.233 (3)
N4—C9	1.370 (3)	C30—C31	1.495 (3)
N4—C3	1.412 (3)	C31—C32	1.382 (3)
C2—C3	1.428 (3)	C31—C36	1.393 (3)
C3—C30	1.429 (3)	C32—C33	1.376 (3)
C2—O2	1.226 (3)	C32—H32	0.9300
C2—N1	1.412 (3)	C33—C34	1.377 (3)
N1—C9	1.346 (3)	C33—H33	0.9300
N1—C11	1.450 (3)	C34—C35	1.374 (3)
C9—C8	1.378 (3)	C35—C36	1.369 (3)
C8—C7	1.364 (4)	C35—H35	0.9300
C8—H8	0.9300	C36—H36	0.9300
C7—C6	1.382 (4)	C11—H11A	0.9600
C7—H7	0.9300	C11—H11B	0.9600
C6—C5	1.364 (4)	C11—H11C	0.9600
C6—H6	0.9300
C5—N4—C9	120.6 (2)	O30—C30—C3	122.5 (2)
C5—N4—C3	129.8 (2)	O30—C30—C31	119.0 (2)
C9—N4—C3	109.5 (2)	C3—C30—C31	118.5 (2)
N4—C3—C2	106.7 (2)	C32—C31—C36	118.5 (2)
N4—C3—C30	122.5 (2)	C32—C31—C30	122.7 (2)
C2—C3—C30	130.7 (2)	C36—C31—C30	118.6 (2)
O2—C2—N1	122.1 (2)	C33—C32—C31	121.4 (2)
O2—C2—C3	133.4 (2)	C33—C32—H32	119.3
N1—C2—C3	104.5 (2)	C31—C32—H32	119.3
C9—N1—C2	111.7 (2)	C32—C33—C34	118.4 (2)
C9—N1—C11	125.1 (2)	C32—C33—H33	120.8
C2—N1—C11	123.1 (2)	C34—C33—H33	120.8
N1—C9—N4	107.5 (2)	C35—C34—C33	121.7 (2)
N1—C9—C8	131.5 (3)	C35—C34—Cl34	119.5 (2)
N4—C9—C8	121.0 (3)	C33—C34—Cl34	118.8 (2)
C7—C8—C9	118.4 (3)	C36—C35—C34	119.1 (2)
C7—C8—H8	120.8	C36—C35—H35	120.4
C9—C8—H8	120.8	C34—C35—H35	120.4
C8—C7—C6	120.2 (3)	C35—C36—C31	120.8 (2)
C8—C7—H7	119.9	C35—C36—H36	119.6
C6—C7—H7	119.9	C31—C36—H36	119.6
C5—C6—C7	121.3 (3)	N1—C11—H11A	109.5
C5—C6—H6	119.4	N1—C11—H11B	109.5
C7—C6—H6	119.4	N1—C11—H11C	109.5
C6—C5—N4	118.5 (3)	H11A—C11—H11B	109.5
C6—C5—H5	120.7	H11A—C11—H11C	109.5
N4—C5—H5	120.7	H11B—C11—H11C	109.5
C5—N4—C3—C2	−179.6 (2)	C8—C7—C6—C5	0.1 (5)
C9—N4—C3—C2	2.5 (3)	C7—C6—C5—N4	−0.2 (4)
C5—N4—C3—C30	−2.0 (4)	C9—N4—C5—C6	0.3 (4)
C9—N4—C3—C30	−179.9 (2)	C3—N4—C5—C6	−177.5 (2)
N4—C3—C2—O2	176.9 (3)	N4—C3—C30—O30	−13.5 (4)
C30—C3—C2—O2	−0.5 (5)	C2—C3—C30—O30	163.5 (3)
N4—C3—C2—N1	−2.5 (3)	N4—C3—C30—C31	164.6 (2)
C30—C3—C2—N1	−179.8 (3)	C2—C3—C30—C31	−18.4 (4)
O2—C2—N1—C9	−177.7 (2)	O30—C30—C31—C32	136.1 (3)
C3—C2—N1—C9	1.8 (3)	C3—C30—C31—C32	−42.1 (4)
O2—C2—N1—C11	−2.0 (4)	O30—C30—C31—C36	−38.7 (4)
C3—C2—N1—C11	177.5 (2)	C3—C30—C31—C36	143.1 (2)
C2—N1—C9—N4	−0.3 (3)	C36—C31—C32—C33	0.7 (4)
C11—N1—C9—N4	−175.9 (2)	C30—C31—C32—C33	−174.1 (2)
C2—N1—C9—C8	−179.5 (3)	C31—C32—C33—C34	−0.5 (4)
C11—N1—C9—C8	4.9 (5)	C32—C33—C34—C35	−0.9 (4)
C5—N4—C9—N1	−179.5 (2)	C32—C33—C34—Cl34	−179.66 (19)
C3—N4—C9—N1	−1.4 (3)	C33—C34—C35—C36	2.0 (4)
C5—N4—C9—C8	−0.2 (4)	Cl34—C34—C35—C36	−179.18 (19)
C3—N4—C9—C8	177.9 (3)	C34—C35—C36—C31	−1.8 (4)
N1—C9—C8—C7	179.3 (3)	C32—C31—C36—C35	0.5 (4)
N4—C9—C8—C7	0.1 (4)	C30—C31—C36—C35	175.5 (2)
C9—C8—C7—C6	−0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O30	0.93	2.30	2.863 (3)	119.
C8—H8···O2i	0.93	2.47	3.291 (4)	148.
C32—H32···Cl34ii	0.93	2.93	3.794 (3)	155.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O30	0.93	2.30	2.863 (3)	119
C8—H8⋯O2i	0.93	2.47	3.291 (4)	148
C32—H32⋯Cl34ii	0.93	2.93	3.794 (3)	155

Symmetry codes: (i) ; (ii) .