2-(Hydrazonomethyl)phenol.

The conformation of the title compound, C(7)H(8)N(2)O, is stabilized by an intra-molecular O-H⋯N hydrogen bond. The crystal structure shows inter-molecular N-H⋯O hydrogen bonds.

Related literature

For Schiff bases as mixed-donor ligands in coordination chemistry, see: Lee et al. (2005 ▶). For the pharmaceutical and medicinal activity of Schiff bases, see: Sriram et al. (2006 ▶); Hao (2009 ▶); Bedia et al. (2006 ▶).

Experimental

Crystal data

C7H8N2O

M = 136.15

Monoclinic,

a = 14.1010 (11) Å

b = 6.0062 (5) Å

c = 8.1979 (6) Å

β = 102.5250 (10)°

V = 677.78 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.46 × 0.45 × 0.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.959, T max = 0.968

3351 measured reflections

1203 independent reflections

1081 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.06

1203 reflections

93 parameters

.

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045504/bt5112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045504/bt5112Isup2.hkl

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

C7H8N2O	F(000) = 288
Mr = 136.15	Dx = 1.334 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2298 reflections
a = 14.1010 (11) Å	θ = 3.0–28.4°
b = 6.0062 (5) Å	µ = 0.09 mm−1
c = 8.1979 (6) Å	T = 296 K
β = 102.525 (1)°	Block, yellow
V = 677.78 (9) Å3	0.46 × 0.45 × 0.35 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1203 independent reflections
Radiation source: fine-focus sealed tube	1081 reflections with I > 2σ(I)
graphite	Rint = 0.013
φ and ω scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→16
Tmin = 0.959, Tmax = 0.968	k = −6→7
3351 measured reflections	l = −9→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.33 e Å−3
1203 reflections	Δρmin = −0.29 e Å−3
93 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.129 (12)
Primary atom site location: structure-invariant direct methods

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	0.22022 (10)	−0.1162 (2)	0.13139 (16)	0.0374 (4)
C2	0.27892 (11)	−0.2576 (3)	0.24310 (18)	0.0462 (4)
H2	0.2554	−0.3958	0.2670	0.055*
C3	0.37226 (12)	−0.1944 (3)	0.3192 (2)	0.0546 (5)
H3	0.4111	−0.2898	0.3948	0.065*
C4	0.40836 (11)	0.0097 (3)	0.2837 (2)	0.0568 (5)
H4	0.4715	0.0513	0.3339	0.068*
C5	0.34970 (11)	0.1512 (3)	0.17277 (19)	0.0487 (4)
H5	0.3743	0.2881	0.1487	0.058*
C6	0.25465 (9)	0.0945 (2)	0.09582 (16)	0.0372 (4)
C7	0.19290 (10)	0.2536 (2)	−0.01248 (16)	0.0392 (4)
H7	0.2190	0.3883	−0.0376	0.047*
N1	0.10354 (8)	0.21085 (19)	−0.07344 (14)	0.0407 (3)
N2	0.04759 (9)	0.3659 (2)	−0.17427 (15)	0.0507 (4)
H2A	0.0693	0.4889	−0.2059	0.061*
H2B	−0.0089	0.3460	−0.1530	0.061*
O1	0.12928 (7)	−0.18636 (16)	0.05811 (13)	0.0476 (3)
H1	0.0993	−0.0840	0.0039	0.071*

	U11	U22	U33	U12	U13	U23
C1	0.0428 (8)	0.0355 (7)	0.0358 (7)	−0.0005 (6)	0.0127 (6)	−0.0036 (5)
C2	0.0587 (9)	0.0381 (8)	0.0439 (8)	0.0040 (6)	0.0157 (7)	0.0026 (6)
C3	0.0576 (10)	0.0566 (10)	0.0467 (9)	0.0148 (8)	0.0050 (7)	0.0038 (7)
C4	0.0439 (8)	0.0645 (11)	0.0574 (10)	0.0009 (8)	0.0007 (7)	−0.0041 (8)
C5	0.0468 (8)	0.0447 (8)	0.0543 (9)	−0.0070 (6)	0.0106 (7)	−0.0034 (7)
C6	0.0418 (7)	0.0351 (7)	0.0363 (7)	−0.0016 (6)	0.0118 (5)	−0.0038 (5)
C7	0.0471 (8)	0.0323 (7)	0.0399 (7)	−0.0060 (6)	0.0130 (6)	0.0003 (6)
N1	0.0468 (7)	0.0364 (6)	0.0385 (6)	−0.0013 (5)	0.0083 (5)	0.0020 (5)
N2	0.0523 (8)	0.0466 (8)	0.0522 (8)	0.0037 (6)	0.0092 (6)	0.0140 (6)
O1	0.0451 (6)	0.0353 (6)	0.0607 (7)	−0.0054 (4)	0.0078 (5)	0.0039 (5)

C1—O1	1.3597 (16)	C5—C6	1.3941 (19)
C1—C2	1.384 (2)	C5—H5	0.9300
C1—C6	1.409 (2)	C6—C7	1.4574 (19)
C2—C3	1.382 (2)	C7—N1	1.2768 (18)
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.382 (2)	N1—N2	1.3749 (16)
C3—H3	0.9300	N2—H2A	0.8604
C4—C5	1.381 (2)	N2—H2B	0.8604
C4—H4	0.9300	O1—H1	0.8200
O1—C1—C2	118.26 (12)	C4—C5—H5	119.1
O1—C1—C6	121.42 (12)	C6—C5—H5	119.1
C2—C1—C6	120.32 (13)	C5—C6—C1	117.79 (13)
C3—C2—C1	120.28 (14)	C5—C6—C7	120.29 (13)
C3—C2—H2	119.9	C1—C6—C7	121.88 (12)
C1—C2—H2	119.9	N1—C7—C6	121.00 (12)
C2—C3—C4	120.46 (15)	N1—C7—H7	119.5
C2—C3—H3	119.8	C6—C7—H7	119.5
C4—C3—H3	119.8	C7—N1—N2	119.21 (12)
C5—C4—C3	119.27 (15)	N1—N2—H2A	124.6
C5—C4—H4	120.4	N1—N2—H2B	102.7
C3—C4—H4	120.4	H2A—N2—H2B	125.9
C4—C5—C6	121.86 (14)	C1—O1—H1	109.5
O1—C1—C2—C3	179.29 (13)	O1—C1—C6—C5	−178.27 (12)
C6—C1—C2—C3	−0.8 (2)	C2—C1—C6—C5	1.82 (19)
C1—C2—C3—C4	−0.5 (2)	O1—C1—C6—C7	4.02 (19)
C2—C3—C4—C5	0.8 (2)	C2—C1—C6—C7	−175.89 (12)
C3—C4—C5—C6	0.3 (2)	C5—C6—C7—N1	−174.54 (13)
C4—C5—C6—C1	−1.6 (2)	C1—C6—C7—N1	3.1 (2)
C4—C5—C6—C7	176.17 (13)	C6—C7—N1—N2	179.61 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.56	3.3076 (17)	145
N2—H2B···O1ii	0.86	2.23	3.0530 (16)	160
O1—H1···N1	0.82	1.89	2.6109 (15)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	2.56	3.3076 (17)	145
N2—H2B⋯O1ii	0.86	2.23	3.0530 (16)	160
O1—H1⋯N1	0.82	1.89	2.6109 (15)	147

Symmetry codes: (i) ; (ii) .