3-Hydr­oxy-N′-isopropyl­idene-2-naphthohydrazide

Lee, S.M.; Lo, K.M.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536809050661

organic compounds

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Volume 65| Part 12| December 2009| Page o3282

doi:10.1107/S1600536809050661

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3-Hydroxy-N′-isopropylidene-2-naphthohydrazide

See Mun Lee,^a Kong Mun Lo,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 November 2009; accepted 24 November 2009; online 28 November 2009)

The title Schiff base, C₁₄H₁₄N₂O₂, is close to being planar (r.m.s. deviation for the non-hydrogen atoms = 0.052 Å) and an intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, the moleucles are linked by O—H⋯O hydrogen bonds, giving rise to helical chains propagating along the c axis of the tetragonal unit cell.

Related literature

For the crystal structure of 2′-(2-isopropylidene)-2-hydroxybenzohydrazide monohydrate, see: Kraudelt et al. (1996 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M_r = 242.27
Tetragonal, $[P \overline 42_1 c ]$
a = 13.7343 (3) Å
c = 12.8253 (3) Å
V = 2419.25 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 123 K
0.35 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
16460 measured reflections
1566 independent reflections
1341 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.113
S = 1.01
1566 reflections
173 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.84 (1)	1.87 (2)	2.648 (2)	153 (3)
N1—H1n⋯O1	0.88 (1)	1.93 (2)	2.631 (2)	136 (2)
Symmetry code: (i) $[-y+{\script{3\over 2}}, -x+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050661/hb5249sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050661/hb5249Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of 2'-(2-isopropylidene)-2-hydroxybenzohydrazide monohydrate, see: Kraudelt et al. (1996).

Experimental top

The title Schiff base was obtained as a side product from the reaction between 3-hydroxy-2-naphthoic hydrazide (1 g, 5 mmol) and 4-chlorobenzaldehyde (0.7 g, 5 mmol) in acetone. Colourless irregular chunks of (I) were obtained when the solvent was allowed to evaporate slowly.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-Hydroxy-N'-isopropylidene-2-naphthohydrazide top

Crystal data top

C₁₄H₁₄N₂O₂	D_x = 1.330 Mg m⁻³
M_r = 242.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 2887 reflections
Hall symbol: P -42 n	θ = 2.2–26.0°
a = 13.7343 (3) Å	µ = 0.09 mm⁻¹
c = 12.8253 (3) Å	T = 123 K
V = 2419.25 (8) Å³	Irregular, colourless
Z = 8	0.35 × 0.15 × 0.05 mm
F(000) = 1024

Data collection top

Bruker SMART APEX diffractometer	1341 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Graphite monochromator	θ_max = 27.5°, θ_min = 2.1°
ω scans	h = −17→17
16460 measured reflections	k = −17→17
1566 independent reflections	l = −16→16

Refinement top

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0711P)² + 0.6133P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
1566 reflections	Δρ_max = 0.27 e Å⁻³
173 parameters	Δρ_min = −0.22 e Å⁻³
2 restraints	Absolute structure: Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₄H₁₄N₂O₂	Z = 8
M_r = 242.27	Mo Kα radiation
Tetragonal, P42₁c	µ = 0.09 mm⁻¹
a = 13.7343 (3) Å	T = 123 K
c = 12.8253 (3) Å	0.35 × 0.15 × 0.05 mm
V = 2419.25 (8) Å³

Data collection top

Bruker SMART APEX diffractometer	1341 reflections with I > 2σ(I)
16460 measured reflections	R_int = 0.055
1566 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.27 e Å⁻³
1566 reflections	Δρ_min = −0.22 e Å⁻³
173 parameters	Absolute structure: Friedel pairs were merged

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

	x	y	z	U_iso*/U_eq
O1	0.89011 (13)	0.64858 (12)	0.81784 (12)	0.0232 (4)
H1O	0.879 (3)	0.649 (3)	0.8825 (10)	0.047 (10)*
O2	0.86201 (14)	0.70322 (12)	0.49816 (12)	0.0268 (4)
N1	0.87509 (16)	0.58826 (14)	0.62381 (16)	0.0213 (4)
H1N	0.875 (2)	0.5750 (19)	0.6910 (9)	0.026 (8)*
N2	0.86924 (15)	0.51398 (15)	0.55082 (15)	0.0244 (5)
C1	0.88285 (16)	0.74227 (16)	0.78288 (18)	0.0185 (5)
C2	0.88364 (17)	0.81988 (17)	0.85018 (18)	0.0203 (5)
H2	0.8892	0.8081	0.9229	0.024*
C3	0.87638 (16)	0.91683 (17)	0.81435 (18)	0.0197 (5)
C4	0.87394 (18)	0.99834 (18)	0.88226 (19)	0.0241 (5)
H4	0.8786	0.9887	0.9554	0.029*
C5	0.86503 (19)	1.09039 (18)	0.8436 (2)	0.0275 (6)
H5	0.8640	1.1441	0.8902	0.033*
C6	0.8573 (2)	1.10692 (18)	0.7353 (2)	0.0297 (6)
H6	0.8505	1.1714	0.7094	0.036*
C7	0.85970 (19)	1.03001 (18)	0.6677 (2)	0.0273 (6)
H7	0.8548	1.0413	0.5949	0.033*
C8	0.86940 (17)	0.93370 (16)	0.70538 (19)	0.0195 (5)
C9	0.86959 (17)	0.85281 (18)	0.63782 (19)	0.0215 (5)
H9	0.8657	0.8640	0.5648	0.026*
C10	0.87513 (17)	0.75829 (17)	0.67298 (18)	0.0192 (5)
C11	0.87014 (17)	0.68105 (17)	0.59108 (18)	0.0196 (5)
C12	0.87295 (18)	0.42740 (19)	0.5869 (2)	0.0257 (5)
C13	0.8674 (2)	0.3471 (2)	0.5088 (2)	0.0374 (7)
H13A	0.8575	0.3747	0.4392	0.056*
H13B	0.8129	0.3040	0.5261	0.056*
H13C	0.9282	0.3098	0.5099	0.056*
C14	0.8808 (2)	0.39944 (19)	0.7001 (2)	0.0322 (6)
H14A	0.9250	0.4445	0.7357	0.048*
H14B	0.9063	0.3330	0.7056	0.048*
H14C	0.8163	0.4026	0.7325	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0343 (9)	0.0223 (8)	0.0130 (8)	0.0004 (7)	0.0001 (7)	0.0022 (7)
O2	0.0375 (10)	0.0294 (9)	0.0134 (8)	−0.0015 (8)	−0.0012 (8)	−0.0008 (7)
N1	0.0261 (11)	0.0248 (10)	0.0130 (9)	0.0002 (8)	−0.0002 (8)	−0.0008 (8)
N2	0.0253 (10)	0.0272 (10)	0.0205 (10)	−0.0010 (9)	0.0007 (9)	−0.0064 (9)
C1	0.0166 (11)	0.0208 (11)	0.0179 (11)	−0.0003 (9)	0.0005 (9)	0.0015 (9)
C2	0.0195 (12)	0.0284 (12)	0.0130 (10)	−0.0013 (10)	−0.0018 (9)	−0.0009 (9)
C3	0.0139 (10)	0.0254 (11)	0.0198 (11)	−0.0003 (9)	−0.0002 (9)	0.0000 (10)
C4	0.0235 (12)	0.0253 (12)	0.0235 (12)	0.0007 (10)	−0.0026 (10)	−0.0041 (10)
C5	0.0265 (13)	0.0223 (12)	0.0337 (14)	0.0017 (11)	−0.0006 (12)	−0.0053 (11)
C6	0.0296 (13)	0.0227 (12)	0.0368 (14)	0.0015 (10)	0.0010 (12)	0.0052 (11)
C7	0.0313 (14)	0.0279 (13)	0.0226 (12)	0.0020 (11)	−0.0009 (11)	0.0070 (10)
C8	0.0147 (10)	0.0228 (11)	0.0211 (11)	−0.0004 (9)	−0.0016 (9)	0.0014 (9)
C9	0.0201 (11)	0.0288 (12)	0.0155 (10)	−0.0003 (10)	−0.0003 (9)	0.0027 (10)
C10	0.0167 (11)	0.0242 (11)	0.0168 (11)	−0.0018 (9)	−0.0005 (9)	−0.0014 (9)
C11	0.0160 (10)	0.0262 (12)	0.0167 (11)	−0.0017 (9)	0.0004 (9)	−0.0025 (9)
C12	0.0198 (11)	0.0274 (12)	0.0298 (13)	−0.0026 (10)	−0.0002 (11)	−0.0052 (10)
C13	0.0339 (14)	0.0336 (14)	0.0446 (16)	0.0000 (12)	0.0029 (14)	−0.0146 (13)
C14	0.0337 (14)	0.0281 (13)	0.0348 (15)	−0.0026 (11)	−0.0025 (12)	0.0035 (12)

Geometric parameters (Å, º) top

O1—C1	1.366 (3)	C6—C7	1.367 (4)
O1—H1O	0.843 (10)	C6—H6	0.9500
O2—C11	1.235 (3)	C7—C8	1.414 (3)
N1—C11	1.344 (3)	C7—H7	0.9500
N1—N2	1.387 (3)	C8—C9	1.409 (3)
N1—H1N	0.880 (10)	C9—C10	1.376 (3)
N2—C12	1.277 (3)	C9—H9	0.9500
C1—C2	1.372 (3)	C10—C11	1.494 (3)
C1—C10	1.430 (3)	C12—C13	1.492 (4)
C2—C3	1.412 (3)	C12—C14	1.505 (4)
C2—H2	0.9500	C13—H13A	0.9800
C3—C8	1.420 (3)	C13—H13B	0.9800
C3—C4	1.419 (3)	C13—H13C	0.9800
C4—C5	1.364 (4)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—C6	1.411 (4)	C14—H14C	0.9800
C5—H5	0.9500

C1—O1—H1O	108 (2)	C9—C8—C3	118.5 (2)
C11—N1—N2	118.94 (19)	C7—C8—C3	119.7 (2)
C11—N1—H1N	120.1 (18)	C10—C9—C8	122.8 (2)
N2—N1—H1N	120.6 (18)	C10—C9—H9	118.6
C12—N2—N1	116.0 (2)	C8—C9—H9	118.6
O1—C1—C2	121.7 (2)	C9—C10—C1	118.2 (2)
O1—C1—C10	118.27 (19)	C9—C10—C11	115.9 (2)
C2—C1—C10	120.1 (2)	C1—C10—C11	125.9 (2)
C1—C2—C3	121.8 (2)	O2—C11—N1	122.7 (2)
C1—C2—H2	119.1	O2—C11—C10	120.5 (2)
C3—C2—H2	119.1	N1—C11—C10	116.8 (2)
C2—C3—C8	118.6 (2)	N2—C12—C13	116.3 (2)
C2—C3—C4	123.1 (2)	N2—C12—C14	126.2 (2)
C8—C3—C4	118.3 (2)	C13—C12—C14	117.5 (2)
C5—C4—C3	120.7 (2)	C12—C13—H13A	109.5
C5—C4—H4	119.7	C12—C13—H13B	109.5
C3—C4—H4	119.7	H13A—C13—H13B	109.5
C4—C5—C6	120.9 (2)	C12—C13—H13C	109.5
C4—C5—H5	119.5	H13A—C13—H13C	109.5
C6—C5—H5	119.5	H13B—C13—H13C	109.5
C7—C6—C5	119.9 (2)	C12—C14—H14A	109.5
C7—C6—H6	120.1	C12—C14—H14B	109.5
C5—C6—H6	120.1	H14A—C14—H14B	109.5
C6—C7—C8	120.6 (2)	C12—C14—H14C	109.5
C6—C7—H7	119.7	H14A—C14—H14C	109.5
C8—C7—H7	119.7	H14B—C14—H14C	109.5
C9—C8—C7	121.9 (2)

C11—N1—N2—C12	−179.0 (2)	C7—C8—C9—C10	−177.4 (2)
O1—C1—C2—C3	179.9 (2)	C3—C8—C9—C10	0.8 (4)
C10—C1—C2—C3	0.4 (4)	C8—C9—C10—C1	−1.2 (4)
C1—C2—C3—C8	−0.9 (4)	C8—C9—C10—C11	177.5 (2)
C1—C2—C3—C4	178.0 (2)	O1—C1—C10—C9	−178.9 (2)
C2—C3—C4—C5	−178.8 (2)	C2—C1—C10—C9	0.6 (4)
C8—C3—C4—C5	0.1 (4)	O1—C1—C10—C11	2.6 (4)
C3—C4—C5—C6	0.5 (4)	C2—C1—C10—C11	−177.9 (2)
C4—C5—C6—C7	−0.6 (4)	N2—N1—C11—O2	−1.1 (4)
C5—C6—C7—C8	0.3 (4)	N2—N1—C11—C10	179.0 (2)
C6—C7—C8—C9	178.4 (2)	C9—C10—C11—O2	0.3 (3)
C6—C7—C8—C3	0.2 (4)	C1—C10—C11—O2	178.9 (2)
C2—C3—C8—C9	0.3 (4)	C9—C10—C11—N1	−179.8 (2)
C4—C3—C8—C9	−178.6 (2)	C1—C10—C11—N1	−1.2 (4)
C2—C3—C8—C7	178.5 (2)	N1—N2—C12—C13	−179.6 (2)
C4—C3—C8—C7	−0.4 (4)	N1—N2—C12—C14	1.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84 (1)	1.87 (2)	2.648 (2)	153 (3)
N1—H1n···O1	0.88 (1)	1.93 (2)	2.631 (2)	136 (2)

Symmetry code: (i) −y+3/2, −x+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₂
M_r	242.27
Crystal system, space group	Tetragonal, P42₁c
Temperature (K)	123
a, c (Å)	13.7343 (3), 12.8253 (3)
V (Å³)	2419.25 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16460, 1566, 1341
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.113, 1.01
No. of reflections	1566
No. of parameters	173
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22
Absolute structure	Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84 (1)	1.870 (19)	2.648 (2)	153 (3)
N1—H1n···O1	0.88 (1)	1.93 (2)	2.631 (2)	136 (2)

Symmetry code: (i) −y+3/2, −x+3/2, z+1/2.

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kraudelt, H., Ludwig, E., Schilde, U. & Uhlemann, E. (1996). Z. Naturforsch. Teil B, 51, 563–566. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar