1-(Hydroxy-imino-meth-yl)-2-naphthol.

The title compound, C(11)H(9)NO(2), was prepared by a condens-ation reaction of 2-hydr-oxy-1-naphthaldehyde with hydroxyl-ammonium chloride in refluxing ethanol. An intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen-bond inter-actions result in a two-dimensional network.

Related literature

For general background, see: Desai et al. (2001 ▶); Hodnett et al. (1970 ▶).

Experimental

Crystal data

C11H9NO2

M = 187.19

Monoclinic,

a = 14.8382 (19) Å

b = 4.0462 (7) Å

c = 16.527 (2) Å

β = 114.933 (2)°

V = 899.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.56 × 0.45 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.953, T max = 0.984

3977 measured reflections

1573 independent reflections

1009 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.148

S = 1.04

1573 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 datablocks I, global. DOI: 10.1107/S160053680800370X/fj2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800370X/fj2080Isup2.hkl

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

C11H9NO2	F000 = 392
Mr = 187.19	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1237 reflections
a = 14.8382 (19) Å	θ = 2.5–27.0º
b = 4.0462 (7) Å	µ = 0.10 mm−1
c = 16.527 (2) Å	T = 298 (2) K
β = 114.933 (2)º	Block, yellow
V = 899.8 (2) Å3	0.56 × 0.45 × 0.18 mm
Z = 4

Bruker SMART 1K CCD diffractometer	1573 independent reflections
Radiation source: fine-focus sealed tube	1009 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.053
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −17→15
Tmin = 0.953, Tmax = 0.984	k = −4→4
3977 measured reflections	l = −19→19

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.1603P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1573 reflections	Δρmax = 0.19 e Å−3
127 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.02725 (13)	0.4774 (6)	0.36227 (12)	0.0492 (6)
O1	−0.05788 (11)	0.5784 (5)	0.37113 (10)	0.0675 (6)
H1	−0.0944	0.6796	0.3262	0.101*
O2	0.14880 (11)	0.4181 (5)	0.28864 (9)	0.0576 (6)
H2	0.0978	0.4758	0.2925	0.086*
C1	0.08718 (16)	0.3186 (6)	0.42939 (14)	0.0450 (6)
H1A	0.0709	0.2805	0.4771	0.054*
C2	0.18092 (14)	0.1946 (6)	0.43332 (13)	0.0398 (6)
C3	0.20781 (15)	0.2491 (6)	0.36359 (14)	0.0447 (6)
C4	0.29816 (17)	0.1329 (7)	0.36695 (16)	0.0543 (7)
H4	0.3149	0.1746	0.3197	0.065*
C5	0.36087 (17)	−0.0385 (7)	0.43808 (18)	0.0574 (7)
H5	0.4197	−0.1189	0.4383	0.069*
C6	0.33969 (16)	−0.1004 (6)	0.51308 (16)	0.0498 (7)
C7	0.24800 (15)	0.0168 (6)	0.50985 (14)	0.0426 (6)
C8	0.22784 (17)	−0.0505 (7)	0.58514 (15)	0.0525 (7)
H8	0.1680	0.0189	0.5849	0.063*
C9	0.29445 (19)	−0.2143 (7)	0.65726 (17)	0.0627 (7)
H9	0.2795	−0.2534	0.7057	0.075*
C10	0.38420 (19)	−0.3245 (7)	0.66013 (19)	0.0707 (8)
H10	0.4294	−0.4333	0.7104	0.085*
C11	0.40583 (18)	−0.2721 (7)	0.58864 (19)	0.0634 (8)
H11	0.4653	−0.3514	0.5900	0.076*

	U11	U22	U33	U12	U13	U23
N1	0.0425 (10)	0.0617 (16)	0.0470 (11)	0.0002 (10)	0.0225 (9)	−0.0005 (10)
O1	0.0471 (9)	0.1046 (17)	0.0565 (10)	0.0234 (10)	0.0274 (8)	0.0178 (11)
O2	0.0556 (10)	0.0760 (14)	0.0459 (9)	−0.0074 (9)	0.0260 (8)	−0.0040 (9)
C1	0.0442 (13)	0.0525 (17)	0.0411 (11)	−0.0030 (12)	0.0207 (10)	−0.0005 (12)
C2	0.0390 (12)	0.0386 (15)	0.0440 (11)	−0.0084 (11)	0.0196 (10)	−0.0125 (11)
C3	0.0429 (12)	0.0469 (16)	0.0451 (12)	−0.0123 (12)	0.0195 (10)	−0.0131 (12)
C4	0.0516 (14)	0.060 (2)	0.0611 (15)	−0.0153 (13)	0.0333 (13)	−0.0238 (15)
C5	0.0419 (13)	0.0546 (19)	0.0820 (17)	−0.0088 (13)	0.0322 (13)	−0.0240 (16)
C6	0.0382 (12)	0.0392 (16)	0.0676 (15)	−0.0088 (11)	0.0180 (12)	−0.0152 (13)
C7	0.0398 (12)	0.0355 (15)	0.0515 (13)	−0.0087 (10)	0.0184 (10)	−0.0121 (12)
C8	0.0519 (14)	0.0489 (18)	0.0569 (14)	0.0029 (12)	0.0232 (12)	0.0007 (13)
C9	0.0660 (17)	0.054 (2)	0.0632 (15)	0.0036 (15)	0.0220 (14)	0.0115 (15)
C10	0.0581 (17)	0.054 (2)	0.0781 (18)	0.0009 (14)	0.0070 (15)	0.0103 (16)
C11	0.0430 (14)	0.0439 (18)	0.0911 (19)	0.0002 (13)	0.0165 (14)	−0.0073 (16)

N1—C1	1.266 (3)	C5—C6	1.423 (3)
N1—O1	1.393 (2)	C5—H5	0.9300
O1—H1	0.8200	C6—C11	1.404 (3)
O2—C3	1.362 (3)	C6—C7	1.420 (3)
O2—H2	0.8200	C7—C8	1.423 (3)
C1—C2	1.454 (3)	C8—C9	1.358 (3)
C1—H1A	0.9300	C8—H8	0.9300
C2—C3	1.387 (3)	C9—C10	1.386 (3)
C2—C7	1.431 (3)	C9—H9	0.9300
C3—C4	1.399 (3)	C10—C11	1.365 (4)
C4—C5	1.344 (3)	C10—H10	0.9300
C4—H4	0.9300	C11—H11	0.9300
C1—N1—O1	112.96 (16)	C11—C6—C7	119.9 (2)
N1—O1—H1	109.5	C11—C6—C5	122.2 (2)
C3—O2—H2	109.5	C7—C6—C5	117.9 (2)
N1—C1—C2	121.31 (19)	C6—C7—C8	117.0 (2)
N1—C1—H1A	119.3	C6—C7—C2	119.96 (19)
C2—C1—H1A	119.3	C8—C7—C2	123.0 (2)
C3—C2—C7	118.56 (19)	C9—C8—C7	121.2 (2)
C3—C2—C1	120.9 (2)	C9—C8—H8	119.4
C7—C2—C1	120.59 (18)	C7—C8—H8	119.4
O2—C3—C2	122.40 (19)	C8—C9—C10	121.4 (2)
O2—C3—C4	116.27 (19)	C8—C9—H9	119.3
C2—C3—C4	121.3 (2)	C10—C9—H9	119.3
C5—C4—C3	120.4 (2)	C11—C10—C9	119.6 (3)
C5—C4—H4	119.8	C11—C10—H10	120.2
C3—C4—H4	119.8	C9—C10—H10	120.2
C4—C5—C6	121.8 (2)	C10—C11—C6	121.0 (2)
C4—C5—H5	119.1	C10—C11—H11	119.5
C6—C5—H5	119.1	C6—C11—H11	119.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.86	2.577 (2)	146
O1—H1···O2i	0.82	1.97	2.771 (2)	164
C1—H1A···O1ii	0.93	2.66	3.527 (3)	156
C8—H8···O1ii	0.93	2.62	3.474 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.86	2.577 (2)	146
O1—H1⋯O2i	0.82	1.97	2.771 (2)	164
C1—H1A⋯O1ii	0.93	2.66	3.527 (3)	156
C8—H8⋯O1ii	0.93	2.62	3.474 (3)	153

Symmetry codes: (i) ; (ii) .