1-(Hydroxy­imino­meth­yl)-2-naphthol

Guo, Z.; Li, L.; Liu, G.; Dong, J.

doi:10.1107/S160053680800370X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o568

doi:10.1107/S160053680800370X

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1-(Hydroxyiminomethyl)-2-naphthol

Zhenghua Guo,^a Lianzhi Li,^a ^* Guihua Liu ^a and Jianfang Dong ^a

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: lilianzhi1963@yahoo.com.cn

(Received 16 November 2007; accepted 3 February 2008; online 8 February 2008)

The title compound, C₁₁H₉NO₂, was prepared by a condensation reaction of 2-hydroxy-1-naphthaldehyde with hydroxylammonium chloride in refluxing ethanol. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen-bond interactions 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_r = 187.19
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.148
S = 1.04
1573 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800370X/fj2080sup1.cif

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

checkCIF report

Comment top

Schiff bases have been intensively investigated owing to their strong coordination capability and diverse biological activities, such as antibacterial, antitumor activities(Desai et al., 2001; Hodnett et al., 1970). We report here the synthesis and crystal structure of a new Schiff base compound derived from the condensation of 2-hydroxy-1-naphthaldehyde and hydroxylammonium chioride.

In the molecular structure(Scheme 1 and Fig.1), all the atoms are almost in one plane, with the C?N = 1.266 (3) Å. In the molecule, an intramolecular O2—H2···N1 hydrogen bond is observed(Table 1). The interactions of intermolecular hydrogen bond O1—H1···O2 form a one-dimensional chain-like structure(Fig. 2), which together with another two intermolecular H atoms C1—H1a···O1 and C8—H8···O1 (Table 1) result in the two-dimensional net-shaped structure.

Related literature top

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

Experimental top

2-hydroxy-1-naphthaldehyde (1 mmol, 172.18 mg) in absolute ethanol (5 ml) was added dropwise to a absolute ethanol solution (10 ml) of hydroxylammonium chioride (1 mmol, 69.49 mg). The mixture was heated under reflux with stirring for 2 h and then filtered. The resulting solution was held at room temperature for 14 days, whereupon the colourless needle crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title complex, viewed approximately along the a axis.

1-(Hydroxyiminomethyl)-2-naphthol top

Crystal data top

C₁₁H₉NO₂	F(000) = 392
M_r = 187.19	D_x = 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 = 2.5–27.0°
b = 4.0462 (7) Å	µ = 0.10 mm⁻¹
c = 16.527 (2) Å	T = 298 K
β = 114.933 (2)°	Block, yellow
V = 899.8 (2) Å³	0.56 × 0.45 × 0.18 mm
Z = 4

Data collection top

Bruker SMART 1K CCD diffractometer	1573 independent reflections
Radiation source: fine-focus sealed tube	1009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→15
T_min = 0.953, T_max = 0.984	k = −4→4
3977 measured reflections	l = −19→19

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0623P)² + 0.1603P] where P = (F_o² + 2F_c²)/3
1573 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₁H₉NO₂	V = 899.8 (2) Å³
M_r = 187.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.8382 (19) Å	µ = 0.10 mm⁻¹
b = 4.0462 (7) Å	T = 298 K
c = 16.527 (2) Å	0.56 × 0.45 × 0.18 mm
β = 114.933 (2)°

Data collection top

Bruker SMART 1K CCD diffractometer	1573 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1009 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.984	R_int = 0.053
3977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
1573 reflections	Δρ_min = −0.20 e Å⁻³
127 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₉NO₂
M_r	187.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.8382 (19), 4.0462 (7), 16.527 (2)
β (°)	114.933 (2)
V (Å³)	899.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.56 × 0.45 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3977, 1573, 1009
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.149, 1.04
No. of reflections	1573
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1.

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (No. Y2004B02) for a research grant.

References

Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Hetercycle Commun. 7, 83–90. CAS Google Scholar
Hodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem. 13, 786–788. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar