2-Hydr­oxy-N′-[(E)-(3-hydr­oxy-2-naphth­yl)methyl­ene]benzohydrazide

Sun, Y.; Li, H.-G.; Wang, X.; Fu, S.; Wang, D.

doi:10.1107/S1600536808044073

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o262

doi:10.1107/S1600536808044073

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ADDENDA AND ERRATA

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2-Hydroxy-N′-[(E)-(3-hydroxy-2-naphthyl)methylene]benzohydrazide

Yuying Sun,^a Hong-Gang Li,^b Xiao Wang,^c Shizhou Fu ^c and Daqi Wang ^c ^*

^aAnalytical and Testing Center of Beihua University, Jilin 132013, People's Republic of China, ^bClinical Medicine Department, Weifang Medical University, Weifang, Shangdong 261042, People's Republic of China, and ^cDepartment of Chemistry, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: wdq@lcu.edu.cn

(Received 13 December 2008; accepted 27 December 2008; online 8 January 2009)

In the title molecule, C₁₈H₁₄N₂O₃, O—H⋯N and N—H⋯O hydrogen bonds influence the molecular conformation; the benzene and naphthalene planes are inclined at a dihedral angle of 11.54 (5)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains running in the [01 $[\overline{1}]$ ] direction.

Related literature

For useful applications of salicyloyl hydrazide derivatives, see: Sumita et al. (1999 ). For the crystal structure of (E)-2-hydroxy-N′-(3-hydroxy-4-methoxybenzylidene)benzohydrazide, see: Luo (2007 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₃
M_r = 306.31
Orthorhombic, P n a 2₁
a = 21.124 (2) Å
b = 11.6212 (13) Å
c = 5.9826 (8) Å
V = 1468.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.32 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.986
6099 measured reflections
1422 independent reflections
896 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.076
S = 1.04
1422 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.90	2.623 (5)	146
N1—H1⋯O2	0.86	1.92	2.620 (4)	137
O2—H2⋯O1ⁱ	0.82	1.81	2.573 (4)	155
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808044073/cv2501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808044073/cv2501Isup2.hkl

checkCIF report

Comment top

Salicyloyl hydrazide is an important organic intermediate, it can act as moulding board in inorganic complex (Sumita et al., 1999). In this paper, we present the title compound (I), which was synthesized by the reaction of 2-hydroxyl naphthaldehyde and salicyloyl hydrazide.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Luo, 2007). In the crystal structure, the C8=N2 bond length is 1.279 (5) Å showing the double-bond character. The dihedral angle between the naphthalene ring and C8/N2/N1 is 10.14 (3) Å, the C1/N1/N2 and benzene ring form a dihedral angle of 6.70 (4) Å showing that intramolecular O—H···N and N—H···O hydrogen bonds (Table 1) influence the molecular conformation.

In the crystal, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains running in direction [01–1].

Related literature top

For useful applications of salicyloyl hydrazide derivatives, see: Sumita et al. (1999). For the crystal structure of (E)-2-hydroxy-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide, see: Luo (2007).

Experimental top

Salicyloyl hydrazide (0.5 mmol) and freshly 2-hydroxyl naphthaldehyde (0.5 mmol) were mixed in 50 ml flash. After stirring 30 min at 353 K, the mixture then cooling slowly to room temperature and affording the title compound, then recrystallized from ethanol, affording the title compound as a green crystalline solid. Elemental analysis: calculated for C₁₈H₁₄N₂O₃: C 70.58, H 4.61, N 9.15%; found: C 70.53, H 4.55, N 9.24%.

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. ORTEP drawing of the title molecule with atomic numbering scheme and displacement ellipsoids at 30% probability level.

2-Hydroxy-N'-[(E)-(3-hydroxy-2-naphthyl)methylene]benzohydrazide top

Crystal data top

C₁₈H₁₄N₂O₃	D_x = 1.385 Mg m⁻³
M_r = 306.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1119 reflections
a = 21.124 (2) Å	θ = 2.6–25.4°
b = 11.6212 (13) Å	µ = 0.10 mm⁻¹
c = 5.9826 (8) Å	T = 298 K
V = 1468.6 (3) Å³	Block, yellow
Z = 4	0.32 × 0.18 × 0.15 mm
F(000) = 640

Data collection top

Bruker SMART CCD area-detector diffractometer	1422 independent reflections
Radiation source: fine-focus sealed tube	896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.970, T_max = 0.986	k = −13→8
6099 measured reflections	l = −7→6

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0012P)² + 0.7621P] where P = (F_o² + 2F_c²)/3
1422 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₁₄N₂O₃	V = 1468.6 (3) Å³
M_r = 306.31	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 21.124 (2) Å	µ = 0.10 mm⁻¹
b = 11.6212 (13) Å	T = 298 K
c = 5.9826 (8) Å	0.32 × 0.18 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1422 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	896 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.986	R_int = 0.057
6099 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	Δρ_max = 0.15 e Å⁻³
1422 reflections	Δρ_min = −0.16 e Å⁻³
209 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	0.22373 (16)	0.9395 (3)	0.7320 (6)	0.0514 (10)
H1	0.2172	0.8713	0.7828	0.062*
N2	0.19138 (18)	0.9753 (3)	0.5434 (6)	0.0536 (11)
O1	0.27673 (14)	1.1075 (2)	0.7748 (6)	0.0703 (10)
O2	0.25278 (12)	0.7725 (2)	1.0077 (6)	0.0574 (9)
H2	0.2526	0.7107	1.0739	0.086*
O3	0.16012 (13)	1.1067 (3)	0.2045 (6)	0.0664 (10)
H3	0.1787	1.0892	0.3199	0.100*
C1	0.2649 (2)	1.0079 (4)	0.8375 (8)	0.0504 (12)
C2	0.2955 (2)	0.9611 (3)	1.0404 (8)	0.0447 (11)
C3	0.2891 (2)	0.8497 (3)	1.1229 (7)	0.0441 (12)
C4	0.3185 (2)	0.8179 (4)	1.3196 (8)	0.0544 (13)
H4	0.3135	0.7435	1.3740	0.065*
C5	0.3548 (2)	0.8948 (5)	1.4348 (9)	0.0672 (15)
H5	0.3750	0.8718	1.5655	0.081*
C6	0.3618 (2)	1.0054 (5)	1.3596 (10)	0.0718 (16)
H6	0.3863	1.0578	1.4392	0.086*
C7	0.3321 (2)	1.0378 (4)	1.1646 (10)	0.0614 (14)
H7	0.3366	1.1130	1.1142	0.074*
C8	0.1536 (2)	0.8994 (4)	0.4641 (8)	0.0546 (13)
H8	0.1507	0.8288	0.5363	0.066*
C9	0.1152 (2)	0.9189 (4)	0.2659 (8)	0.0493 (12)
C10	0.1211 (2)	1.0193 (4)	0.1429 (8)	0.0495 (12)
C11	0.0868 (2)	1.0370 (4)	−0.0549 (8)	0.0560 (13)
H11	0.0914	1.1054	−0.1339	0.067*
C12	0.0468 (2)	0.9542 (4)	−0.1312 (9)	0.0607 (14)
H12	0.0255	0.9653	−0.2656	0.073*
C13	0.0369 (2)	0.8510 (4)	−0.0089 (9)	0.0548 (13)
C14	0.07102 (19)	0.8331 (4)	0.1920 (8)	0.0511 (12)
C15	0.0568 (2)	0.7320 (4)	0.3138 (9)	0.0656 (15)
H15	0.0780	0.7173	0.4470	0.079*
C16	0.0128 (2)	0.6564 (5)	0.2396 (11)	0.0790 (19)
H16	0.0044	0.5909	0.3239	0.095*
C17	−0.0202 (2)	0.6734 (5)	0.0415 (12)	0.0771 (17)
H17	−0.0500	0.6199	−0.0067	0.093*
C18	−0.0082 (2)	0.7700 (4)	−0.0809 (9)	0.0686 (16)
H18	−0.0301	0.7825	−0.2136	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.053 (2)	0.058 (2)	0.043 (3)	0.005 (2)	−0.001 (2)	0.022 (2)
N2	0.051 (2)	0.070 (3)	0.040 (2)	0.016 (2)	0.000 (2)	0.017 (2)
O1	0.086 (2)	0.0454 (18)	0.079 (3)	0.0026 (17)	0.004 (2)	0.0291 (19)
O2	0.076 (2)	0.0427 (16)	0.053 (2)	−0.0038 (16)	−0.012 (2)	0.0166 (17)
O3	0.063 (2)	0.081 (2)	0.056 (3)	−0.0053 (18)	−0.0055 (19)	0.029 (2)
C1	0.052 (3)	0.049 (3)	0.050 (3)	0.007 (2)	0.006 (3)	0.012 (2)
C2	0.046 (3)	0.043 (3)	0.044 (3)	0.005 (2)	0.001 (2)	0.009 (2)
C3	0.050 (3)	0.042 (3)	0.040 (3)	0.000 (2)	−0.001 (2)	0.005 (2)
C4	0.060 (3)	0.058 (3)	0.045 (3)	0.008 (3)	0.001 (3)	0.017 (3)
C5	0.062 (3)	0.087 (4)	0.053 (4)	0.012 (3)	−0.010 (3)	0.003 (3)
C6	0.065 (3)	0.073 (4)	0.077 (4)	−0.006 (3)	−0.012 (3)	−0.011 (3)
C7	0.066 (3)	0.050 (3)	0.068 (4)	−0.002 (3)	0.002 (3)	0.007 (3)
C8	0.055 (3)	0.062 (3)	0.047 (3)	0.013 (3)	0.007 (3)	0.018 (3)
C9	0.047 (3)	0.063 (3)	0.037 (3)	0.011 (2)	0.005 (2)	0.014 (3)
C10	0.044 (3)	0.068 (3)	0.037 (3)	0.007 (2)	0.007 (3)	0.016 (3)
C11	0.054 (3)	0.075 (3)	0.039 (3)	0.011 (3)	−0.001 (3)	0.020 (3)
C12	0.059 (3)	0.088 (4)	0.035 (3)	0.009 (3)	0.000 (3)	0.007 (3)
C13	0.049 (3)	0.064 (3)	0.051 (3)	0.009 (3)	0.009 (3)	0.001 (3)
C14	0.049 (3)	0.059 (3)	0.046 (3)	0.017 (2)	0.006 (3)	0.004 (3)
C15	0.056 (3)	0.071 (3)	0.070 (4)	0.008 (3)	0.000 (3)	0.017 (3)
C16	0.069 (4)	0.068 (4)	0.100 (6)	0.003 (3)	0.001 (4)	0.018 (4)
C17	0.068 (4)	0.067 (4)	0.096 (5)	−0.003 (3)	0.002 (4)	0.001 (4)
C18	0.060 (3)	0.079 (4)	0.066 (4)	0.007 (3)	0.008 (3)	−0.008 (4)

Geometric parameters (Å, º) top

N1—C1	1.336 (5)	C8—C9	1.455 (6)
N1—N2	1.383 (5)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.386 (5)
N2—C8	1.280 (5)	C9—C14	1.435 (5)
O1—C1	1.242 (5)	C10—C11	1.403 (6)
O2—C3	1.366 (5)	C11—C12	1.360 (6)
O2—H2	0.8200	C11—H11	0.9300
O3—C10	1.359 (5)	C12—C13	1.420 (6)
O3—H3	0.8200	C12—H12	0.9300
C1—C2	1.479 (6)	C13—C18	1.407 (6)
C2—C3	1.392 (5)	C13—C14	1.417 (6)
C2—C7	1.395 (6)	C14—C15	1.415 (6)
C3—C4	1.381 (6)	C15—C16	1.354 (6)
C4—C5	1.364 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.389 (7)
C5—C6	1.370 (7)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.364 (6)
C6—C7	1.377 (7)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300

C1—N1—N2	121.8 (4)	C10—C9—C14	118.7 (4)
C1—N1—H1	119.1	C10—C9—C8	120.9 (4)
N2—N1—H1	119.1	C14—C9—C8	120.4 (4)
C8—N2—N1	113.8 (4)	O3—C10—C9	122.7 (4)
C3—O2—H2	109.5	O3—C10—C11	115.7 (4)
C10—O3—H3	109.5	C9—C10—C11	121.6 (5)
O1—C1—N1	122.9 (4)	C12—C11—C10	120.1 (5)
O1—C1—C2	120.2 (5)	C12—C11—H11	120.0
N1—C1—C2	116.9 (4)	C10—C11—H11	120.0
C3—C2—C7	117.3 (4)	C11—C12—C13	121.1 (5)
C3—C2—C1	126.2 (4)	C11—C12—H12	119.5
C7—C2—C1	116.4 (4)	C13—C12—H12	119.5
O2—C3—C4	120.5 (4)	C18—C13—C14	120.4 (5)
O2—C3—C2	119.1 (4)	C18—C13—C12	120.4 (5)
C4—C3—C2	120.5 (4)	C14—C13—C12	119.1 (5)
C5—C4—C3	120.6 (5)	C15—C14—C13	116.8 (5)
C5—C4—H4	119.7	C15—C14—C9	123.8 (5)
C3—C4—H4	119.7	C13—C14—C9	119.4 (4)
C4—C5—C6	120.6 (5)	C16—C15—C14	121.1 (5)
C4—C5—H5	119.7	C16—C15—H15	119.5
C6—C5—H5	119.7	C14—C15—H15	119.5
C5—C6—C7	119.0 (5)	C15—C16—C17	122.1 (6)
C5—C6—H6	120.5	C15—C16—H16	118.9
C7—C6—H6	120.5	C17—C16—H16	118.9
C6—C7—C2	122.0 (5)	C18—C17—C16	118.8 (6)
C6—C7—H7	119.0	C18—C17—H17	120.6
C2—C7—H7	119.0	C16—C17—H17	120.6
N2—C8—C9	122.9 (4)	C17—C18—C13	120.8 (6)
N2—C8—H8	118.6	C17—C18—H18	119.6
C9—C8—H8	118.6	C13—C18—H18	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.90	2.623 (5)	146
N1—H1···O2	0.86	1.92	2.620 (4)	137
O2—H2···O1ⁱ	0.82	1.81	2.573 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₃
M_r	306.31
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	21.124 (2), 11.6212 (13), 5.9826 (8)
V (Å³)	1468.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	6099, 1422, 896
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.076, 1.04
No. of reflections	1422
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

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
O3—H3···N2	0.82	1.90	2.623 (5)	146.4
N1—H1···O2	0.86	1.92	2.620 (4)	137.3
O2—H2···O1ⁱ	0.82	1.81	2.573 (4)	154.7

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

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).

References

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Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
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