N'-Hy-droxy-pyridine-2-carboximidamide.

The title mol-ecule, C6H7N3O, is almost planar (r.m.s. deviation = 0.0068 Å) and adopts an E conformation about the C=N double bond. In the crystal, mol-ecules are linked by pairs of strong N-H⋯N hydrogen bonds, forming inversion dimers with R 2 (2)(10) motifs. The dimers are further linked into C(3) chains through O-H⋯N hydrogen bonds.

Related literature

For the pharmaceutical and biological activity of substituted N′-hy­droxy­benzamidines and 1,2,4-oxa­diazole derivatives, see: Kundu et al. (2012 ▶); Sakamoto et al. (2007 ▶); Tyrkov & Sukhenko (2004 ▶). For a related structure, see: Sreenivasa et al. (2012 ▶)

Experimental

Crystal data

C6H7N3O

M = 137.15

Monoclinic,

a = 21.367 (5) Å

b = 4.6382 (11) Å

c = 13.003 (3) Å

β = 105.468 (12)°

V = 1242.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.33 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.979

8242 measured reflections

1086 independent reflections

982 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.08

1086 reflections

103 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT-Plus and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017418/bt6916sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017418/bt6916Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017418/bt6916Isup3.cml

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

C6H7N3O	F(000) = 576
Mr = 137.15	prism
Monoclinic, C2/c	Dx = 1.467 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 21.367 (5) Å	Cell parameters from 1088 reflections
b = 4.6382 (11) Å	θ = 2.0–25.0°
c = 13.003 (3) Å	µ = 0.11 mm−1
β = 105.468 (12)°	T = 293 K
V = 1242.0 (5) Å3	Prism, colourless
Z = 8	0.33 × 0.25 × 0.20 mm

Bruker APEXII CCD area-detector diffractometer	1086 independent reflections
Radiation source: fine-focus sealed tube	982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 1.03 pixels mm-1	θmax = 25.0°, θmin = 2.0°
phi and ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −5→5
Tmin = 0.966, Tmax = 0.979	l = −15→15
8242 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.8786P] where P = (Fo2 + 2Fc2)/3
1086 reflections	(Δ/σ)max = 0.011
103 parameters	Δρmax = 0.19 e Å−3
2 restraints	Δρmin = −0.18 e Å−3
0 constraints

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
O1	0.19134 (4)	0.1826 (2)	0.26040 (7)	0.0207 (3)
H1N2	0.0896 (7)	0.225 (3)	0.1797 (12)	0.027 (4)*
H2N2	0.0456 (6)	0.081 (3)	0.0861 (11)	0.027 (4)*
H1	0.2316 (9)	0.260 (4)	0.2779 (14)	0.043 (5)*
C1	0.12315 (6)	−0.2716 (3)	0.03188 (9)	0.0154 (3)
C2	0.17439 (6)	−0.4236 (3)	0.01036 (10)	0.0189 (3)
H2	0.2167	−0.3964	0.0520	0.023*
C3	0.16144 (6)	−0.6149 (3)	−0.07361 (10)	0.0208 (3)
H3	0.1949	−0.7164	−0.0904	0.025*
C4	0.09770 (6)	−0.6536 (3)	−0.13259 (10)	0.0211 (3)
H4	0.0874	−0.7834	−0.1891	0.025*
C5	0.05004 (6)	−0.4948 (3)	−0.10538 (10)	0.0203 (3)
H5	0.0073	−0.5229	−0.1449	0.024*
C6	0.13390 (5)	−0.0595 (3)	0.12070 (9)	0.0147 (3)
N1	0.06133 (5)	−0.3023 (2)	−0.02561 (8)	0.0176 (3)
N2	0.08163 (5)	0.0824 (2)	0.13540 (9)	0.0179 (3)
N3	0.19228 (5)	−0.0259 (2)	0.18081 (8)	0.0175 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0156 (5)	0.0240 (5)	0.0199 (5)	−0.0027 (4)	0.0004 (4)	−0.0070 (4)
C1	0.0157 (6)	0.0151 (6)	0.0149 (6)	−0.0009 (5)	0.0032 (5)	0.0048 (5)
C2	0.0152 (6)	0.0215 (7)	0.0186 (6)	0.0008 (5)	0.0022 (5)	0.0038 (5)
C3	0.0225 (7)	0.0210 (7)	0.0205 (7)	0.0050 (5)	0.0087 (5)	0.0035 (5)
C4	0.0276 (7)	0.0199 (7)	0.0157 (6)	0.0005 (5)	0.0055 (5)	−0.0008 (5)
C5	0.0175 (6)	0.0231 (7)	0.0173 (6)	−0.0017 (5)	−0.0006 (5)	−0.0008 (5)
C6	0.0142 (6)	0.0154 (6)	0.0141 (6)	0.0000 (5)	0.0029 (5)	0.0046 (5)
N1	0.0155 (5)	0.0193 (6)	0.0162 (5)	−0.0008 (4)	0.0012 (4)	0.0004 (4)
N2	0.0130 (6)	0.0216 (6)	0.0162 (6)	0.0013 (5)	−0.0009 (5)	−0.0031 (5)
N3	0.0163 (5)	0.0177 (6)	0.0169 (5)	−0.0009 (4)	0.0018 (4)	−0.0017 (4)

O1—N3	1.4201 (13)	C4—C5	1.3773 (18)
O1—H1	0.903 (18)	C4—H4	0.9300
C1—N1	1.3407 (16)	C5—N1	1.3408 (16)
C1—C2	1.3918 (17)	C5—H5	0.9300
C1—C6	1.4878 (17)	C6—N3	1.2928 (16)
C2—C3	1.3765 (18)	C6—N2	1.3532 (16)
C2—H2	0.9300	N2—H1N2	0.862 (13)
C3—C4	1.3849 (19)	N2—H2N2	0.859 (13)
C3—H3	0.9300
N3—O1—H1	104.9 (11)	C3—C4—H4	120.9
N1—C1—C2	123.03 (11)	N1—C5—C4	124.19 (12)
N1—C1—C6	115.35 (10)	N1—C5—H5	117.9
C2—C1—C6	121.61 (11)	C4—C5—H5	117.9
C3—C2—C1	118.91 (12)	N3—C6—N2	123.75 (11)
C3—C2—H2	120.5	N3—C6—C1	118.26 (10)
C1—C2—H2	120.5	N2—C6—C1	117.97 (10)
C2—C3—C4	118.86 (12)	C1—N1—C5	116.69 (10)
C2—C3—H3	120.6	C6—N2—H1N2	116.3 (10)
C4—C3—H3	120.6	C6—N2—H2N2	119.9 (10)
C5—C4—C3	118.28 (12)	H1N2—N2—H2N2	118.9 (14)
C5—C4—H4	120.9	C6—N3—O1	108.89 (9)
N1—C1—C2—C3	−0.07 (18)	N1—C1—C6—N2	−0.29 (16)
C6—C1—C2—C3	−179.35 (11)	C2—C1—C6—N2	179.05 (11)
C1—C2—C3—C4	−1.19 (18)	C2—C1—N1—C5	1.51 (17)
C2—C3—C4—C5	0.96 (18)	C6—C1—N1—C5	−179.17 (10)
C3—C4—C5—N1	0.6 (2)	C4—C5—N1—C1	−1.77 (18)
N1—C1—C6—N3	178.22 (10)	N2—C6—N3—O1	−0.96 (16)
C2—C1—C6—N3	−2.45 (17)	C1—C6—N3—O1	−179.38 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.903 (18)	1.859 (19)	2.7537 (14)	170.5 (17)
N2—H2N2···N1ii	0.86 (1)	2.44 (1)	3.1753 (16)	144 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.903 (18)	1.859 (19)	2.7537 (14)	170.5 (17)
N2—H2N2⋯N1ii	0.86 (1)	2.44 (1)	3.1753 (16)	144 (1)

Symmetry codes: (i) ; (ii) .