2-Hy-droxy-N'-methyl-benzohydrazide.

In the title mol-ecule, C(8)H(10)N(2)O(2), there is an intra-molecular hydrogen bond involving the hy-droxy group and the O atom of the carbonyl group. The dihedral angle between the benzene ring and the amide fragment is 87.16 (10)°. The C-N-N-C torsion angle is 88.87 (18)°. In the crystal, N-H⋯N and N-H⋯O hydrogen bonds connect mol-ecules into chains along [100]. In addition, there is a weak C-H⋯π inter-action.

Related literature

For applications of related materials, see: Zhang et al. (2012 ▶); Jin et al. (2011 ▶). For the preparation of the title compound, see: Li et al. (2001 ▶). For a related structure, see: Jin (2007 ▶).

Experimental

Crystal data

C8H10N2O2

M = 166.18

Monoclinic,

a = 7.4863 (10) Å

b = 14.706 (2) Å

c = 7.7232 (11) Å

β = 96.898 (2)°

V = 844.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.981

6478 measured reflections

1837 independent reflections

1381 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.129

S = 1.03

1837 reflections

119 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203468X/lh5501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203468X/lh5501Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203468X/lh5501Isup3.cml

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

C8H10N2O2	F(000) = 352
Mr = 166.18	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1880 reflections
a = 7.4863 (10) Å	θ = 2.7–26.5°
b = 14.706 (2) Å	µ = 0.10 mm−1
c = 7.7232 (11) Å	T = 294 K
β = 96.898 (2)°	Block, colorless
V = 844.1 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	1837 independent reflections
Radiation source: fine-focus sealed tube	1381 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.972, Tmax = 0.981	k = −16→18
6478 measured reflections	l = −9→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0724P)2] where P = (Fo2 + 2Fc2)/3
1837 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.26 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
C1	0.75411 (17)	0.59342 (9)	0.39608 (15)	0.0389 (3)
C2	0.88807 (19)	0.63880 (10)	0.50734 (17)	0.0467 (4)
C3	0.8400 (2)	0.68846 (12)	0.6475 (2)	0.0593 (4)
H3	0.9278	0.7199	0.7192	0.071*
C4	0.6643 (2)	0.69159 (11)	0.68107 (19)	0.0576 (4)
H4	0.6344	0.7240	0.7769	0.069*
C5	0.5313 (2)	0.64697 (10)	0.57369 (18)	0.0496 (4)
H5	0.4122	0.6494	0.5965	0.060*
C6	0.57723 (19)	0.59916 (9)	0.43321 (17)	0.0432 (4)
H6	0.4874	0.5697	0.3605	0.052*
C7	0.80781 (18)	0.54385 (10)	0.24308 (16)	0.0423 (4)
C8	0.7418 (3)	0.36724 (13)	0.0064 (2)	0.0769 (6)
H8A	0.8366	0.3593	0.1005	0.115*
H8B	0.7758	0.3395	−0.0973	0.115*
H8C	0.6338	0.3392	0.0363	0.115*
N1	0.67678 (17)	0.50872 (10)	0.13066 (14)	0.0514 (4)
H1A	0.565 (3)	0.5176 (12)	0.139 (2)	0.062*
N2	0.71005 (17)	0.46382 (10)	−0.02434 (14)	0.0498 (4)
H2A	0.805 (2)	0.4910 (11)	−0.058 (2)	0.060*
O1	1.06320 (14)	0.63710 (9)	0.48180 (15)	0.0688 (4)
H1B	1.071 (3)	0.6000 (15)	0.388 (3)	0.103*
O2	0.96759 (14)	0.53627 (8)	0.21771 (13)	0.0597 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0367 (8)	0.0413 (8)	0.0386 (7)	0.0003 (6)	0.0045 (5)	0.0015 (5)
C2	0.0368 (8)	0.0526 (9)	0.0497 (7)	0.0011 (6)	0.0014 (6)	−0.0013 (6)
C3	0.0537 (10)	0.0643 (11)	0.0576 (9)	−0.0045 (8)	−0.0034 (7)	−0.0194 (7)
C4	0.0604 (11)	0.0587 (10)	0.0547 (8)	0.0022 (8)	0.0112 (7)	−0.0166 (7)
C5	0.0436 (9)	0.0534 (9)	0.0540 (8)	−0.0020 (7)	0.0154 (6)	−0.0050 (7)
C6	0.0397 (8)	0.0466 (8)	0.0438 (7)	−0.0051 (6)	0.0064 (5)	−0.0015 (6)
C7	0.0339 (8)	0.0515 (9)	0.0422 (7)	−0.0005 (6)	0.0069 (5)	0.0013 (6)
C8	0.0874 (15)	0.0714 (14)	0.0732 (11)	0.0043 (10)	0.0149 (9)	−0.0133 (9)
N1	0.0346 (7)	0.0761 (9)	0.0442 (6)	0.0007 (6)	0.0077 (5)	−0.0167 (6)
N2	0.0402 (7)	0.0668 (9)	0.0438 (6)	−0.0031 (6)	0.0113 (5)	−0.0136 (6)
O1	0.0349 (7)	0.0969 (10)	0.0734 (7)	−0.0048 (6)	0.0013 (5)	−0.0247 (7)
O2	0.0352 (6)	0.0868 (9)	0.0586 (6)	−0.0012 (5)	0.0113 (4)	−0.0172 (5)

C1—C6	1.3907 (19)	C6—H6	0.9300
C1—C2	1.4081 (18)	C7—O2	1.2401 (16)
C1—C7	1.4844 (18)	C7—N1	1.3336 (18)
C2—O1	1.3493 (17)	C8—N2	1.455 (2)
C2—C3	1.388 (2)	C8—H8A	0.9600
C3—C4	1.372 (2)	C8—H8B	0.9600
C3—H3	0.9300	C8—H8C	0.9600
C4—C5	1.383 (2)	N1—N2	1.4152 (16)
C4—H4	0.9300	N1—H1A	0.859 (19)
C5—C6	1.3709 (19)	N2—H2A	0.884 (18)
C5—H5	0.9300	O1—H1B	0.91 (2)
C6—C1—C2	118.12 (12)	C1—C6—H6	119.0
C6—C1—C7	123.34 (11)	O2—C7—N1	120.69 (12)
C2—C1—C7	118.52 (13)	O2—C7—C1	121.90 (12)
O1—C2—C3	118.09 (13)	N1—C7—C1	117.40 (12)
O1—C2—C1	122.37 (12)	N2—C8—H8A	109.5
C3—C2—C1	119.53 (14)	N2—C8—H8B	109.5
C4—C3—C2	120.61 (13)	H8A—C8—H8B	109.5
C4—C3—H3	119.7	N2—C8—H8C	109.5
C2—C3—H3	119.7	H8A—C8—H8C	109.5
C3—C4—C5	120.57 (13)	H8B—C8—H8C	109.5
C3—C4—H4	119.7	C7—N1—N2	122.75 (12)
C5—C4—H4	119.7	C7—N1—H1A	122.9 (11)
C6—C5—C4	119.14 (14)	N2—N1—H1A	113.8 (11)
C6—C5—H5	120.4	N1—N2—C8	111.07 (12)
C4—C5—H5	120.4	N1—N2—H2A	105.5 (10)
C5—C6—C1	122.00 (13)	C8—N2—H2A	111.6 (11)
C5—C6—H6	119.0	C2—O1—H1B	106.4 (14)
C6—C1—C2—O1	179.99 (12)	C2—C1—C6—C5	−0.2 (2)
C7—C1—C2—O1	−1.5 (2)	C7—C1—C6—C5	−178.69 (12)
C6—C1—C2—C3	−1.0 (2)	C6—C1—C7—O2	−176.57 (13)
C7—C1—C2—C3	177.58 (13)	C2—C1—C7—O2	5.0 (2)
O1—C2—C3—C4	−179.12 (15)	C6—C1—C7—N1	4.7 (2)
C1—C2—C3—C4	1.8 (2)	C2—C1—C7—N1	−173.80 (13)
C2—C3—C4—C5	−1.4 (2)	O2—C7—N1—N2	−1.9 (2)
C3—C4—C5—C6	0.2 (2)	C1—C7—N1—N2	176.89 (12)
C4—C5—C6—C1	0.6 (2)	C7—N1—N2—C8	88.87 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2	0.91 (2)	1.72 (2)	2.5535 (15)	150 (2)
N1—H1A···N2i	0.859 (19)	2.16 (2)	2.9415 (18)	151.9 (15)
N1—H1A···N1i	0.859 (19)	2.619 (18)	3.1403 (18)	120.4 (13)
N2—H2A···O2ii	0.884 (18)	2.253 (17)	2.9866 (16)	140.3 (14)
C4—H4···Cgiii	0.93	2.83	3.6713 (13)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2	0.91 (2)	1.72 (2)	2.5535 (15)	150 (2)
N1—H1A⋯N2i	0.859 (19)	2.16 (2)	2.9415 (18)	151.9 (15)
N1—H1A⋯N1i	0.859 (19)	2.619 (18)	3.1403 (18)	120.4 (13)
N2—H2A⋯O2ii	0.884 (18)	2.253 (17)	2.9866 (16)	140.3 (14)
C4—H4⋯Cg iii	0.93	2.83	3.6713 (13)	152

Symmetry codes: (i) ; (ii) ; (iii) .