N′-(3-Eth­oxy-2-hydroxy­benzyl­idene)-3-hydroxy­naphthalene-2-carbohydrazide

Lei, J.-T.; Jiang, Y.-X.; Tao, L.-Y.; Huang, S.-S.; Zhang, H.-L.

doi:10.1107/S1600536808010933

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o909

doi:10.1107/S1600536808010933

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N′-(3-Ethoxy-2-hydroxybenzylidene)-3-hydroxynaphthalene-2-carbohydrazide

Jun-Tao Lei,^a Yan-Xia Jiang,^b Li-Yan Tao,^c Shan-Shan Huang ^c ^* and Hou-Li Zhang ^c ^*

^aDepartment of Pharmacopedics, Jilin Medical College, Jilin 132013, People's Republic of China, ^bDepartment of Biochemistry, Jilin Medical College, Jilin 132013, People's Republic of China, and ^cCollege of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China
^*Correspondence e-mail: jlcpcxb@yahoo.com.cn, houlizh@yahoo.com.cn

(Received 15 April 2008; accepted 19 April 2008; online 26 April 2008)

In the molecule of the title compound, C₂₀H₁₈N₂O₄, the dihedral angle between the benzene ring and the naphthyl ring system is 8.5 (2)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background on Schiff base compounds and their biological applications, see: Schiff (1864 ); Brückner et al. (2000 ); Harrop et al. (2003 ); Ren et al. (2002 ). For related structures, see: Diao (2007 ); Diao et al. (2007 , 2008 ); Huang et al. (2007 ); Li et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₄
M_r = 350.36
Monoclinic, C 2/c
a = 28.420 (15) Å
b = 6.456 (5) Å
c = 18.800 (14) Å
β = 100.658 (10)°
V = 3390 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.972, T_max = 0.974
13100 measured reflections
3503 independent reflections
2183 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.178
S = 1.06
3503 reflections
242 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.87	2.661 (3)	161
O3—H3⋯N2	0.82	1.87	2.589 (3)	146
N1—H1A⋯O1	0.900 (10)	1.95 (2)	2.619 (3)	130 (2)
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010933/pv2080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010933/pv2080Isup2.hkl

checkCIF report

Comment top

The compounds derived from the condensation reactions of aldehydes with primary amines are called Schiff base compounds (Schiff, 1864). Schiff base compounds and their metal complexes have attracted much interest for their wide applications, especially for their potential pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). In this paper, the preparation and crystal structure of the title compound, (I), is reported.

In the structure of (I) (Fig. 1), the naphthyl ring and 2-hydroxyphenyl methylidene hydrazide moiety are nearly coplanar with the dihedral angle between the phenyl ring and the naphthyl ring is 8.5 (2) °; the torsion angles C13—C12—N2—N1 and N2—N1—C11—C1 are 3.5 (2) and 1.4 (2)°, respectively. The methoxy group is slightly twisted out of the plane of the phenyl ring with torsion angle C15—O4—C19—C20 being 13.1 (2)°. The molecules of (I) are linked through intermolecular O–H···O hydrogen bonds, forming chains running along the b axis. The structure is further stabilized by intramolecular interactions N1—H1A···O1 and O3—H3···N2 (Table 1). All the bond lengths are within normal ranges (Allen et al., 1987) and comparable to the values observed in other similar compounds (Diao et al., 2008; Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007).

Related literature top

For background on Schiff base compounds and their biological applications, see: Schiff (1864); Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002). For related structures, see: Allen et al. (1987); Diao (2007); Diao et al. (2007, 2008); Huang et al. (2007); Li et al. (2007).

Experimental top

3-Ethoxysalicylaldehyde (0.1 mmol, 16.6 mg) and 3-hydroxynaphthalene-2-carboxylic acid hydrazide (0.1 mmol, 20.2 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for a few days, colorless block-like crystals were formed.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I) with displacement parameters drawn at the 30% probability level.
	Fig. 2. The molecular packing of (I) showing intermolecular hydrogen-bonds with dashed lines.

N'-(3-Ethoxy-2-hydroxybenzylidene)-3-hydroxynaphthalene-2-carbohydrazide top

Crystal data top

C₂₀H₁₈N₂O₄	F(000) = 1472
M_r = 350.36	D_x = 1.373 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1359 reflections
a = 28.420 (15) Å	θ = 2.2–24.3°
b = 6.456 (5) Å	µ = 0.10 mm⁻¹
c = 18.800 (14) Å	T = 298 K
β = 100.658 (10)°	Block, colorless
V = 3390 (4) Å³	0.30 × 0.27 × 0.27 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 26.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −35→35
T_min = 0.972, T_max = 0.974	k = −8→8
13100 measured reflections	l = −23→22

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.178	w = 1/[σ²(F_o²) + 0.1909P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3503 reflections	Δρ_max = 0.24 e Å⁻³
242 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (6)

Crystal data top

C₂₀H₁₈N₂O₄	V = 3390 (4) Å³
M_r = 350.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.420 (15) Å	µ = 0.10 mm⁻¹
b = 6.456 (5) Å	T = 298 K
c = 18.800 (14) Å	0.30 × 0.27 × 0.27 mm
β = 100.658 (10)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3503 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2183 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.974	R_int = 0.057
13100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	1 restraint
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.24 e Å⁻³
3503 reflections	Δρ_min = −0.19 e Å⁻³
242 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
O1	1.00934 (6)	−0.1963 (2)	0.34159 (8)	0.0489 (5)
H1	1.0059	−0.3211	0.3470	0.073*
O2	0.98937 (6)	0.4267 (2)	0.38501 (9)	0.0528 (5)
O3	0.88269 (7)	0.6149 (3)	0.24267 (9)	0.0611 (6)
H3	0.9039	0.5398	0.2644	0.092*
O4	0.81068 (6)	0.8088 (3)	0.16639 (10)	0.0592 (5)
N1	0.96591 (7)	0.1590 (3)	0.31039 (10)	0.0396 (5)
N2	0.93488 (7)	0.2841 (3)	0.26466 (10)	0.0394 (5)
C1	1.02434 (7)	0.1001 (3)	0.41996 (11)	0.0336 (5)
C2	1.03361 (8)	−0.1122 (3)	0.40475 (11)	0.0363 (5)
C3	1.06657 (8)	−0.2231 (3)	0.45120 (13)	0.0405 (6)
H3A	1.0734	−0.3580	0.4390	0.049*
C4	1.09062 (8)	−0.1396 (3)	0.51714 (12)	0.0377 (5)
C5	1.12406 (8)	−0.2534 (4)	0.56714 (14)	0.0467 (6)
H5	1.1314	−0.3888	0.5563	0.056*
C6	1.14561 (9)	−0.1678 (4)	0.63087 (14)	0.0502 (6)
H6	1.1670	−0.2465	0.6635	0.060*
C7	1.13609 (8)	0.0384 (4)	0.64834 (13)	0.0498 (7)
H7	1.1516	0.0960	0.6917	0.060*
C8	1.10409 (8)	0.1528 (4)	0.60139 (12)	0.0431 (6)
H8	1.0976	0.2882	0.6133	0.052*
C9	1.08064 (8)	0.0685 (3)	0.53476 (11)	0.0364 (5)
C10	1.04759 (8)	0.1814 (3)	0.48433 (12)	0.0372 (5)
H10	1.0412	0.3179	0.4952	0.045*
C11	0.99190 (8)	0.2416 (3)	0.37086 (12)	0.0365 (5)
C12	0.91016 (8)	0.2028 (4)	0.20827 (12)	0.0402 (6)
H12	0.9147	0.0643	0.1977	0.048*
C13	0.87471 (8)	0.3253 (4)	0.16007 (12)	0.0392 (6)
C14	0.86145 (8)	0.5211 (4)	0.18082 (12)	0.0426 (6)
C15	0.82336 (9)	0.6255 (4)	0.13816 (13)	0.0471 (6)
C16	0.80210 (9)	0.5426 (4)	0.07255 (13)	0.0562 (7)
H16	0.7776	0.6148	0.0431	0.067*
C17	0.81680 (9)	0.3529 (4)	0.04985 (14)	0.0566 (7)
H17	0.8027	0.3001	0.0049	0.068*
C18	0.85201 (8)	0.2431 (4)	0.09359 (13)	0.0465 (6)
H18	0.8609	0.1134	0.0791	0.056*
C19	0.76647 (9)	0.9005 (4)	0.13279 (16)	0.0612 (8)
H19A	0.7413	0.7971	0.1251	0.073*
H19B	0.7694	0.9590	0.0863	0.073*
C20	0.75477 (11)	1.0676 (4)	0.18230 (17)	0.0764 (9)
H20A	0.7498	1.0067	0.2269	0.115*
H20B	0.7262	1.1384	0.1597	0.115*
H20C	0.7808	1.1643	0.1920	0.115*
H1A	0.9661 (10)	0.0234 (18)	0.2992 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0656 (11)	0.0304 (9)	0.0453 (10)	0.0015 (8)	−0.0038 (8)	−0.0026 (7)
O2	0.0653 (12)	0.0272 (9)	0.0598 (11)	0.0042 (8)	−0.0043 (9)	0.0031 (8)
O3	0.0697 (13)	0.0505 (11)	0.0525 (11)	0.0209 (9)	−0.0165 (9)	−0.0120 (9)
O4	0.0558 (11)	0.0509 (11)	0.0628 (12)	0.0186 (8)	−0.0098 (9)	−0.0038 (9)
N1	0.0435 (11)	0.0338 (10)	0.0395 (11)	0.0055 (9)	0.0022 (9)	0.0036 (9)
N2	0.0412 (11)	0.0362 (11)	0.0388 (11)	0.0058 (8)	0.0020 (9)	0.0052 (9)
C1	0.0351 (12)	0.0299 (12)	0.0364 (12)	−0.0008 (9)	0.0082 (10)	0.0037 (9)
C2	0.0409 (13)	0.0313 (12)	0.0365 (12)	−0.0030 (10)	0.0066 (10)	0.0005 (10)
C3	0.0442 (14)	0.0308 (12)	0.0473 (14)	0.0021 (10)	0.0105 (11)	0.0017 (10)
C4	0.0351 (12)	0.0369 (13)	0.0422 (13)	0.0013 (10)	0.0099 (10)	0.0020 (10)
C5	0.0451 (14)	0.0446 (14)	0.0514 (15)	0.0114 (11)	0.0114 (12)	0.0047 (12)
C6	0.0422 (14)	0.0616 (17)	0.0448 (15)	0.0093 (12)	0.0029 (12)	0.0051 (12)
C7	0.0435 (15)	0.0634 (18)	0.0410 (14)	−0.0001 (12)	0.0041 (12)	−0.0010 (12)
C8	0.0463 (14)	0.0407 (13)	0.0430 (14)	−0.0013 (11)	0.0098 (11)	−0.0030 (11)
C9	0.0369 (12)	0.0394 (13)	0.0342 (12)	−0.0012 (10)	0.0099 (10)	0.0025 (10)
C10	0.0442 (13)	0.0275 (11)	0.0413 (13)	−0.0002 (10)	0.0113 (11)	0.0009 (10)
C11	0.0379 (12)	0.0312 (13)	0.0407 (13)	−0.0006 (10)	0.0077 (10)	0.0045 (10)
C12	0.0438 (14)	0.0388 (13)	0.0395 (13)	0.0073 (10)	0.0118 (11)	−0.0009 (10)
C13	0.0394 (13)	0.0432 (13)	0.0357 (13)	0.0042 (10)	0.0086 (10)	0.0016 (10)
C14	0.0427 (14)	0.0478 (15)	0.0349 (12)	0.0048 (11)	0.0009 (11)	0.0013 (11)
C15	0.0449 (14)	0.0476 (15)	0.0469 (14)	0.0064 (12)	0.0032 (12)	0.0020 (12)
C16	0.0531 (17)	0.0645 (18)	0.0455 (15)	0.0097 (13)	−0.0052 (12)	0.0103 (13)
C17	0.0573 (17)	0.0694 (19)	0.0389 (14)	0.0010 (14)	−0.0023 (12)	−0.0065 (13)
C18	0.0496 (15)	0.0490 (15)	0.0418 (14)	0.0010 (12)	0.0106 (12)	−0.0036 (11)
C19	0.0419 (15)	0.0561 (17)	0.081 (2)	0.0104 (12)	−0.0009 (14)	0.0025 (15)
C20	0.0619 (19)	0.066 (2)	0.101 (2)	0.0174 (15)	0.0127 (18)	−0.0019 (18)

Geometric parameters (Å, º) top

O1—C2	1.370 (3)	C7—C8	1.362 (3)
O1—H1	0.8200	C7—H7	0.9300
O2—C11	1.230 (3)	C8—C9	1.414 (3)
O3—C14	1.350 (3)	C8—H8	0.9300
O3—H3	0.8200	C9—C10	1.408 (3)
O4—C15	1.372 (3)	C10—H10	0.9300
O4—C19	1.426 (3)	C12—C13	1.457 (3)
N1—C11	1.346 (3)	C12—H12	0.9300
N1—N2	1.374 (2)	C13—C14	1.395 (3)
N1—H1A	0.900 (10)	C13—C18	1.401 (3)
N2—C12	1.272 (3)	C14—C15	1.396 (3)
C1—C10	1.371 (3)	C15—C16	1.377 (3)
C1—C2	1.434 (3)	C16—C17	1.387 (4)
C1—C11	1.490 (3)	C16—H16	0.9300
C2—C3	1.360 (3)	C17—C18	1.369 (3)
C3—C4	1.407 (3)	C17—H17	0.9300
C3—H3A	0.9300	C18—H18	0.9300
C4—C5	1.413 (3)	C19—C20	1.501 (4)
C4—C9	1.425 (3)	C19—H19A	0.9700
C5—C6	1.358 (3)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—C7	1.409 (4)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600

C2—O1—H1	109.5	O2—C11—N1	121.5 (2)
C14—O3—H3	109.5	O2—C11—C1	121.1 (2)
C15—O4—C19	117.36 (19)	N1—C11—C1	117.43 (19)
C11—N1—N2	118.96 (19)	N2—C12—C13	120.4 (2)
C11—N1—H1A	123.8 (18)	N2—C12—H12	119.8
N2—N1—H1A	117.1 (18)	C13—C12—H12	119.8
C12—N2—N1	118.05 (19)	C14—C13—C18	119.3 (2)
C10—C1—C2	117.73 (19)	C14—C13—C12	120.6 (2)
C10—C1—C11	117.0 (2)	C18—C13—C12	120.0 (2)
C2—C1—C11	125.3 (2)	O3—C14—C13	123.1 (2)
C3—C2—O1	121.6 (2)	O3—C14—C15	117.0 (2)
C3—C2—C1	120.3 (2)	C13—C14—C15	119.8 (2)
O1—C2—C1	118.02 (19)	O4—C15—C16	125.3 (2)
C2—C3—C4	121.9 (2)	O4—C15—C14	115.2 (2)
C2—C3—H3A	119.0	C16—C15—C14	119.5 (2)
C4—C3—H3A	119.0	C15—C16—C17	120.8 (2)
C3—C4—C5	123.0 (2)	C15—C16—H16	119.6
C3—C4—C9	118.7 (2)	C17—C16—H16	119.6
C5—C4—C9	118.3 (2)	C18—C17—C16	120.0 (2)
C6—C5—C4	120.9 (2)	C18—C17—H17	120.0
C6—C5—H5	119.6	C16—C17—H17	120.0
C4—C5—H5	119.6	C17—C18—C13	120.3 (2)
C5—C6—C7	121.0 (2)	C17—C18—H18	119.8
C5—C6—H6	119.5	C13—C18—H18	119.8
C7—C6—H6	119.5	O4—C19—C20	107.5 (2)
C8—C7—C6	119.7 (2)	O4—C19—H19A	110.2
C8—C7—H7	120.2	C20—C19—H19A	110.2
C6—C7—H7	120.2	O4—C19—H19B	110.2
C7—C8—C9	120.9 (2)	C20—C19—H19B	110.2
C7—C8—H8	119.5	H19A—C19—H19B	108.5
C9—C8—H8	119.5	C19—C20—H20A	109.5
C10—C9—C8	122.9 (2)	C19—C20—H20B	109.5
C10—C9—C4	117.9 (2)	H20A—C20—H20B	109.5
C8—C9—C4	119.2 (2)	C19—C20—H20C	109.5
C1—C10—C9	123.3 (2)	H20A—C20—H20C	109.5
C1—C10—H10	118.4	H20B—C20—H20C	109.5
C9—C10—H10	118.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.87	2.661 (3)	161
O3—H3···N2	0.82	1.87	2.589 (3)	146
N1—H1A···O1	0.90 (1)	1.95 (2)	2.619 (3)	130 (2)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₄
M_r	350.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.420 (15), 6.456 (5), 18.800 (14)
β (°)	100.658 (10)
V (Å³)	3390 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.972, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	13100, 3503, 2183
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.178, 1.06
No. of reflections	3503
No. of parameters	242
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.87	2.661 (3)	161
O3—H3···N2	0.82	1.87	2.589 (3)	146
N1—H1A···O1	0.900 (10)	1.95 (2)	2.619 (3)	130 (2)

Symmetry code: (i) x, y−1, z.

Acknowledgements

We thank Dr Yun-Peng Diao for assistance with the experiment and structure refinement. The project was supported financially by Jilin Medical College.

References

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Volume 64| Part 5| May 2008| Page o909

doi:10.1107/S1600536808010933

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-(3-Eth­­oxy-2-hy­droxy­benzyl­­idene)-3-hy­droxy­naphthalene-2-carbohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(3-Ethoxy-2-hydroxybenzylidene)-3-hydroxynaphthalene-2-carbohydrazide