Crystal structure of 6-eth-oxy-pyridin-1-ium-2-olate.

In the title compound, C7H9NO2, all non-H atoms are essentially coplanar [r.m.s. deviation = 0.032 Å]. The largest deviation from the plane of the pyridine ring is 0.105 (6) Å for the terminal C atom of the eth-oxy group. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers. These dimers are further linked by C-H⋯π inter-actions and weak π-π inter-actions between pyridine rings [centroid-centroid distance = 4.023 (1) Å].

Related literature

For general background to 2-iodo-5-hy­droxy­pyridine derivatives and their applications, see: Cho et al. (2003 ▶); Hegmann et al. (2003 ▶); Savelon et al. (1998 ▶); Wang et al. (2012 ▶). For the synthesis of the title compound, see: Hutchinson et al. (2001 ▶); Seton et al. (2001 ▶).

Experimental

Crystal data

C7H9NO2

M = 139.15

Monoclinic,

a = 8.3037 (11) Å

b = 7.0999 (6) Å

c = 12.0767 (15) Å

β = 93.402 (13)°

V = 710.74 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.3 × 0.3 × 0.2 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.606, T max = 1.000

2957 measured reflections

1452 independent reflections

949 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.150

S = 1.09

1452 reflections

96 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814020224/zq2227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020224/zq2227Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814020224/zq2227Isup3.txt

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814020224/zq2227Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814020224/zq2227fig1.tif

The mol­ecular structure of the title complex, with non-hydrogen atoms labels and 50% probability displacement ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S1600536814020224/zq2227fig2.tif

Packing of the title compound viewed along the b direction.

CCDC reference: 1023404

Additional supporting information: crystallographic information; 3D view; checkCIF report

C7H9NO2	F(000) = 296
Mr = 139.15	Dx = 1.300 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 809 reflections
a = 8.3037 (11) Å	θ = 3.8–24.3°
b = 7.0999 (6) Å	µ = 0.10 mm−1
c = 12.0767 (15) Å	T = 293 K
β = 93.402 (13)°	Block, white
V = 710.74 (14) Å3	0.3 × 0.3 × 0.2 mm
Z = 4

Agilent Xcalibur Eos diffractometer	1452 independent reflections
Radiation source: Enhance (Mo) X-ray Source	949 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→8
Tmin = 0.606, Tmax = 1.000	l = −7→15
2957 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.055	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.0301P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.24 e Å−3
1452 reflections	Δρmin = −0.33 e Å−3
96 parameters

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. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement.

	x	y	z	Uiso*/Ueq
C1	0.6392 (2)	0.3124 (3)	0.59009 (17)	0.0554 (5)
C2	0.7456 (3)	0.1850 (3)	0.64769 (19)	0.0642 (6)
H2	0.7774	0.2064	0.7218	0.077*
C3	0.8004 (3)	0.0333 (3)	0.5951 (2)	0.0688 (7)
H3	0.8694	−0.0493	0.6344	0.083*
C4	0.7581 (3)	−0.0052 (3)	0.4841 (2)	0.0663 (7)
H4	0.7979	−0.1108	0.4492	0.080*
C5	0.6563 (2)	0.1176 (2)	0.42860 (18)	0.0521 (5)
C6	0.6502 (3)	−0.0472 (3)	0.2572 (2)	0.0683 (7)
H6A	0.6240	−0.1649	0.2928	0.082*
H6B	0.7658	−0.0431	0.2495	0.082*
C7	0.5627 (3)	−0.0328 (4)	0.1469 (2)	0.0824 (8)
H7A	0.5910	−0.1376	0.1017	0.124*
H7B	0.5919	0.0825	0.1117	0.124*
H7C	0.4486	−0.0338	0.1557	0.124*
N1	0.60093 (19)	0.2701 (2)	0.48106 (14)	0.0507 (5)
H1	0.538 (3)	0.350 (3)	0.445 (2)	0.082 (8)*
O1	0.58033 (19)	0.4567 (2)	0.63138 (12)	0.0762 (5)
O2	0.60054 (17)	0.11012 (17)	0.32261 (12)	0.0629 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0558 (12)	0.0567 (11)	0.0530 (12)	−0.0021 (9)	−0.0032 (10)	0.0008 (10)
C2	0.0651 (14)	0.0644 (12)	0.0619 (14)	0.0015 (10)	−0.0066 (11)	0.0103 (11)
C3	0.0624 (14)	0.0641 (13)	0.0792 (17)	0.0075 (11)	−0.0027 (12)	0.0185 (12)
C4	0.0646 (14)	0.0521 (11)	0.0828 (18)	0.0098 (10)	0.0096 (13)	0.0026 (11)
C5	0.0504 (11)	0.0462 (10)	0.0603 (13)	−0.0039 (8)	0.0081 (10)	−0.0007 (9)
C6	0.0732 (15)	0.0593 (12)	0.0738 (16)	0.0059 (10)	0.0173 (13)	−0.0164 (11)
C7	0.0939 (19)	0.0759 (15)	0.0782 (18)	0.0062 (13)	0.0121 (15)	−0.0260 (13)
N1	0.0508 (10)	0.0472 (9)	0.0536 (10)	0.0040 (7)	0.0000 (8)	−0.0025 (8)
O1	0.0997 (13)	0.0716 (10)	0.0550 (10)	0.0237 (9)	−0.0148 (9)	−0.0131 (7)
O2	0.0732 (10)	0.0531 (8)	0.0628 (10)	0.0086 (6)	0.0059 (8)	−0.0118 (7)

C1—C2	1.418 (3)	C5—O2	1.336 (2)
C1—N1	1.369 (2)	C6—H6A	0.9700
C1—O1	1.251 (2)	C6—H6B	0.9700
C2—H2	0.9300	C6—C7	1.483 (3)
C2—C3	1.344 (3)	C6—O2	1.442 (2)
C3—H3	0.9300	C7—H7A	0.9600
C3—C4	1.392 (3)	C7—H7B	0.9600
C4—H4	0.9300	C7—H7C	0.9600
C4—C5	1.363 (3)	N1—H1	0.87 (3)
C5—N1	1.349 (2)
N1—C1—C2	115.75 (19)	C7—C6—H6A	110.2
O1—C1—C2	125.0 (2)	C7—C6—H6B	110.2
O1—C1—N1	119.25 (17)	O2—C6—H6A	110.2
C1—C2—H2	120.1	O2—C6—H6B	110.2
C3—C2—C1	119.9 (2)	O2—C6—C7	107.33 (18)
C3—C2—H2	120.1	C6—C7—H7A	109.5
C2—C3—H3	118.7	C6—C7—H7B	109.5
C2—C3—C4	122.6 (2)	C6—C7—H7C	109.5
C4—C3—H3	118.7	H7A—C7—H7B	109.5
C3—C4—H4	121.3	H7A—C7—H7C	109.5
C5—C4—C3	117.5 (2)	H7B—C7—H7C	109.5
C5—C4—H4	121.3	C1—N1—H1	116.0 (17)
N1—C5—C4	120.1 (2)	C5—N1—C1	124.13 (18)
O2—C5—C4	127.98 (19)	C5—N1—H1	119.9 (17)
O2—C5—N1	111.91 (17)	C5—O2—C6	117.46 (16)
H6A—C6—H6B	108.5
C1—C2—C3—C4	0.5 (3)	C7—C6—O2—C5	175.32 (18)
C2—C1—N1—C5	0.8 (3)	N1—C1—C2—C3	−0.7 (3)
C2—C3—C4—C5	−0.3 (3)	N1—C5—O2—C6	−179.67 (16)
C3—C4—C5—N1	0.3 (3)	O1—C1—C2—C3	179.4 (2)
C3—C4—C5—O2	179.6 (2)	O1—C1—N1—C5	−179.39 (18)
C4—C5—N1—C1	−0.6 (3)	O2—C5—N1—C1	−179.95 (16)
C4—C5—O2—C6	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (2)	1.90 (2)	2.762 (2)	174 (2)
C7—H7A···Cgii	0.96	2.90	3.792 (3)	155

Table 1

Hydrogen-bond geometry (, )

Cg is the centroid of the N1,C1C5 ring.

DHA	DH	HA	D A	DHA
N1H1O1i	0.87(2)	1.90(2)	2.762(2)	174(2)
C7H7A Cg ii	0.96	2.90	3.792(3)	155

Symmetry codes: (i) ; (ii) .