(E)-2-Hydroxy­naphthalene-1-carb­al­de­hyde semicarbazone

Xu, H.-J.; Du, N.-N.; Jiang, X.-Y.; Sheng, L.-Q.; Tian, Y.-P.

doi:10.1107/S160053680901174X

organic compounds

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Volume 65| Part 5| May 2009| Page o1047

doi:10.1107/S160053680901174X

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(E)-2-Hydroxynaphthalene-1-carbaldehyde semicarbazone

Hua-Jie Xu,^a,^b Na-Na Du,^b Xue-Yue Jiang,^b Liang-Quan Sheng ^b ^* and Yu-Peng Tian ^a

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and ^bDepartment of Chemistry, Fuyang Normal College, Fuyang, Anhui 236041, People's Republic of China
^*Correspondence e-mail: shenglq@fync.edu.cn

(Received 23 March 2009; accepted 30 March 2009; online 18 April 2009)

The title compound, C₁₂H₁₁N₃O₂, adopts an E or trans configuration with respect to the C=N bond. There is an intramolecular O—H⋯N hydrogen bond involving the hydroxyl H atom and an N atom of the hydrazine group. In the crystal structure, molecules are connected via N—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the potential pharmacological and antitumor properties of hydrazones and Schiff bases, see: Karthikeyan et al. (2006 ); Khattab (2005 ); Kucukguzel et al. (2006 ). For related structures, see: Okabe et al. (1993 ); Zhang et al. (1999 ); Xu et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₂
M_r = 229.24
Monoclinic, P 2₁ /c
a = 16.091 (3) Å
b = 4.7350 (9) Å
c = 15.776 (3) Å
β = 114.26 (3)°
V = 1095.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 283 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.988, T_max = 0.989
6629 measured reflections
2324 independent reflections
1550 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.05
2324 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.5563 (15)	146
N2—H2⋯O2ⁱ	0.86	2.01	2.8385 (15)	163
N3—H3A⋯O1ⁱⁱ	0.86	2.14	2.9871 (15)	171
N3—H3B⋯O2ⁱⁱⁱ	0.86	2.63	3.0957 (16)	115
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z.

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 global, I. DOI: 10.1107/S160053680901174X/su2105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901174X/su2105Isup2.hkl

checkCIF report

Comment top

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). As we are interested in this field of research (Xu et al. 2009), we report herein on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1 and geometrical parameters are given in the archived CIF. The molecule has a trans configuration about the C=N bond. There is an intramolecular O-H···N hydrogen bond involving the naphthalene hydroxyl sunstituent and atom N1 of the hydrazine group (Table 1).

In the crystal structure symmetry related molecules are connected via N-H···O hydrogen bonds so forming a three-dimensional structure (Table 1 and Fig. 2).

Related literature top

For the potential pharmacological and antitumor properties of hydrazones and Schiff bases, see: Karthikeyan et al. (2006); Khattab (2005); Kucukguzel et al. (2006). For related structures, see: Okabe et al. (1993); Zhang et al. (1999); Xu et al. (2009).

Experimental top

The ligand H₂L was prepared according to the reported procedure (Zhang et al., 1999). A solution of semicarbazide hydrochloride (0.112 g, 1 mmol) in 5 ml of ethanol was added slowly to a solution of 2-hydro-1- naphthaldehyde (0.172 g,1 mmol) in 15 ml absolute ethanol, under heating and stirring. The mixture was refluxed for 3 h, then cooled to rt and left to stand in air for 5 days. Yellow block-shaped crystals were formed on slow evaporation of the solvent.

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 molecular structure of the title compound, showing 30% probability displacement ellipsoids (H-atoms have been omitted for clarity).
	Fig. 2. Crystal packing of the title compound viewed along the b axis. The intra- and intermolecular hydrogen bonds are shown as dashed lines (details are given in Table 1).

(E)-2-Hydroxynaphthalene-1-carbaldehyde semicarbazone top

Crystal data top

C₁₂H₁₁N₃O₂	F(000) = 480
M_r = 229.24	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 628 reflections
a = 16.091 (3) Å	θ = 2.5–15°
b = 4.7350 (9) Å	µ = 0.10 mm⁻¹
c = 15.776 (3) Å	T = 283 K
β = 114.26 (3)°	Block, yellow
V = 1095.8 (4) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2324 independent reflections
Radiation source: fine-focus sealed tube	1550 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.988, T_max = 0.989	k = −6→4
6629 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0607P)²] where P = (F_o² + 2F_c²)/3
2324 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₂H₁₁N₃O₂	V = 1095.8 (4) Å³
M_r = 229.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.091 (3) Å	µ = 0.10 mm⁻¹
b = 4.7350 (9) Å	T = 283 K
c = 15.776 (3) Å	0.20 × 0.10 × 0.10 mm
β = 114.26 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2324 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1550 reflections with I > 2σ(I)
T_min = 0.988, T_max = 0.989	R_int = 0.015
6629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
2324 reflections	Δρ_min = −0.15 e Å⁻³
155 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
C1	0.23742 (8)	0.2085 (3)	0.15396 (8)	0.0367 (3)
C2	0.24256 (9)	0.1120 (3)	0.23930 (9)	0.0441 (3)
C3	0.30716 (10)	−0.0898 (3)	0.29109 (10)	0.0538 (4)
H3C	0.3094	−0.1497	0.3481	0.065*
C4	0.36618 (10)	−0.1978 (3)	0.25859 (10)	0.0530 (4)
H4A	0.4089	−0.3307	0.2939	0.064*
C5	0.36419 (8)	−0.1126 (3)	0.17185 (9)	0.0435 (3)
C6	0.42499 (10)	−0.2280 (3)	0.13721 (11)	0.0572 (4)
H6A	0.4674	−0.3622	0.1722	0.069*
C7	0.42258 (10)	−0.1462 (4)	0.05361 (12)	0.0623 (4)
H7A	0.4634	−0.2231	0.0320	0.075*
C8	0.35881 (11)	0.0531 (3)	0.00052 (11)	0.0571 (4)
H8A	0.3572	0.1088	−0.0567	0.068*
C9	0.29852 (9)	0.1678 (3)	0.03161 (9)	0.0477 (4)
H9A	0.2560	0.2989	−0.0053	0.057*
C10	0.29938 (8)	0.0915 (3)	0.11853 (9)	0.0377 (3)
C11	0.17325 (8)	0.4299 (3)	0.10430 (9)	0.0383 (3)
H11	0.1777	0.5185	0.0537	0.046*
C12	−0.01922 (9)	0.7854 (3)	0.10281 (9)	0.0405 (3)
N1	0.11062 (7)	0.5029 (2)	0.13008 (7)	0.0419 (3)
N2	0.05492 (7)	0.7251 (2)	0.08591 (7)	0.0447 (3)
H2	0.0671	0.8266	0.0473	0.054*
N3	−0.04085 (8)	0.6020 (3)	0.15536 (8)	0.0551 (4)
H3A	−0.0873	0.6333	0.1678	0.066*
H3B	−0.0083	0.4530	0.1765	0.066*
O1	0.18694 (7)	0.2086 (2)	0.27791 (7)	0.0616 (3)
H1	0.1521	0.3272	0.2436	0.092*
O2	−0.06341 (7)	1.00232 (19)	0.07058 (6)	0.0510 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0325 (6)	0.0356 (7)	0.0400 (7)	−0.0004 (5)	0.0127 (6)	0.0012 (6)
C2	0.0426 (7)	0.0456 (8)	0.0445 (7)	0.0005 (6)	0.0183 (6)	0.0036 (6)
C3	0.0547 (9)	0.0555 (9)	0.0458 (8)	0.0047 (7)	0.0151 (7)	0.0146 (7)
C4	0.0425 (8)	0.0467 (9)	0.0575 (9)	0.0073 (7)	0.0080 (7)	0.0094 (7)
C5	0.0317 (7)	0.0378 (8)	0.0543 (8)	−0.0019 (6)	0.0108 (6)	−0.0042 (6)
C6	0.0386 (8)	0.0501 (9)	0.0765 (11)	0.0066 (7)	0.0172 (7)	−0.0063 (8)
C7	0.0479 (8)	0.0625 (11)	0.0841 (12)	0.0004 (8)	0.0347 (8)	−0.0223 (9)
C8	0.0560 (9)	0.0636 (10)	0.0593 (9)	−0.0035 (8)	0.0313 (8)	−0.0097 (8)
C9	0.0436 (8)	0.0519 (9)	0.0478 (8)	0.0035 (6)	0.0191 (7)	−0.0028 (6)
C10	0.0313 (6)	0.0356 (7)	0.0438 (7)	−0.0040 (5)	0.0131 (6)	−0.0052 (6)
C11	0.0371 (7)	0.0381 (8)	0.0389 (7)	−0.0001 (6)	0.0150 (6)	0.0004 (6)
C12	0.0416 (7)	0.0368 (8)	0.0434 (7)	0.0014 (6)	0.0177 (6)	−0.0071 (6)
N1	0.0385 (6)	0.0396 (6)	0.0480 (6)	0.0057 (5)	0.0182 (5)	0.0030 (5)
N2	0.0428 (6)	0.0401 (7)	0.0560 (7)	0.0097 (5)	0.0250 (6)	0.0108 (5)
N3	0.0579 (8)	0.0484 (8)	0.0733 (8)	0.0123 (6)	0.0414 (7)	0.0112 (6)
O1	0.0642 (7)	0.0759 (8)	0.0575 (6)	0.0184 (6)	0.0378 (6)	0.0190 (5)
O2	0.0525 (6)	0.0432 (6)	0.0616 (6)	0.0139 (5)	0.0280 (5)	0.0039 (5)

Geometric parameters (Å, º) top

C1—C2	1.3916 (17)	C8—C9	1.3667 (18)
C1—C10	1.4390 (16)	C8—H8A	0.9300
C1—C11	1.4540 (17)	C9—C10	1.4126 (18)
C2—O1	1.3525 (15)	C9—H9A	0.9300
C2—C3	1.4013 (19)	C11—N1	1.2798 (15)
C3—C4	1.352 (2)	C11—H11	0.9300
C3—H3C	0.9300	C12—O2	1.2336 (14)
C4—C5	1.414 (2)	C12—N3	1.3417 (16)
C4—H4A	0.9300	C12—N2	1.3554 (15)
C5—C6	1.4120 (19)	N1—N2	1.3719 (14)
C5—C10	1.4172 (18)	N2—H2	0.8600
C6—C7	1.360 (2)	N3—H3A	0.8600
C6—H6A	0.9300	N3—H3B	0.8600
C7—C8	1.392 (2)	O1—H1	0.8200
C7—H7A	0.9300

C2—C1—C10	118.31 (12)	C9—C8—H8A	119.7
C2—C1—C11	120.31 (11)	C7—C8—H8A	119.7
C10—C1—C11	121.34 (11)	C8—C9—C10	121.44 (14)
O1—C2—C1	122.52 (12)	C8—C9—H9A	119.3
O1—C2—C3	115.95 (12)	C10—C9—H9A	119.3
C1—C2—C3	121.53 (12)	C9—C10—C5	117.51 (11)
C4—C3—C2	120.36 (13)	C9—C10—C1	123.13 (12)
C4—C3—H3C	119.8	C5—C10—C1	119.36 (11)
C2—C3—H3C	119.8	N1—C11—C1	120.08 (11)
C3—C4—C5	121.27 (13)	N1—C11—H11	120.0
C3—C4—H4A	119.4	C1—C11—H11	120.0
C5—C4—H4A	119.4	O2—C12—N3	122.80 (12)
C6—C5—C4	121.35 (14)	O2—C12—N2	119.96 (12)
C6—C5—C10	119.48 (13)	N3—C12—N2	117.24 (12)
C4—C5—C10	119.17 (12)	C11—N1—N2	118.76 (10)
C7—C6—C5	121.13 (15)	C12—N2—N1	120.39 (10)
C7—C6—H6A	119.4	C12—N2—H2	119.8
C5—C6—H6A	119.4	N1—N2—H2	119.8
C6—C7—C8	119.79 (13)	C12—N3—H3A	120.0
C6—C7—H7A	120.1	C12—N3—H3B	120.0
C8—C7—H7A	120.1	H3A—N3—H3B	120.0
C9—C8—C7	120.64 (14)	C2—O1—H1	109.5

C10—C1—C2—O1	−179.71 (12)	C8—C9—C10—C1	179.65 (12)
C11—C1—C2—O1	2.7 (2)	C6—C5—C10—C9	0.63 (18)
C10—C1—C2—C3	1.2 (2)	C4—C5—C10—C9	−179.00 (12)
C11—C1—C2—C3	−176.41 (13)	C6—C5—C10—C1	179.93 (12)
O1—C2—C3—C4	−179.60 (13)	C4—C5—C10—C1	0.30 (18)
C1—C2—C3—C4	−0.4 (2)	C2—C1—C10—C9	178.15 (12)
C2—C3—C4—C5	−0.4 (2)	C11—C1—C10—C9	−4.27 (19)
C3—C4—C5—C6	−179.15 (13)	C2—C1—C10—C5	−1.10 (18)
C3—C4—C5—C10	0.5 (2)	C11—C1—C10—C5	176.48 (11)
C4—C5—C6—C7	179.75 (13)	C2—C1—C11—N1	−12.17 (19)
C10—C5—C6—C7	0.1 (2)	C10—C1—C11—N1	170.30 (11)
C5—C6—C7—C8	−0.5 (2)	C1—C11—N1—N2	175.68 (11)
C6—C7—C8—C9	0.0 (2)	O2—C12—N2—N1	172.35 (11)
C7—C8—C9—C10	0.8 (2)	N3—C12—N2—N1	−7.35 (18)
C8—C9—C10—C5	−1.1 (2)	C11—N1—N2—C12	171.46 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.5563 (15)	146
N2—H2···O2ⁱ	0.86	2.01	2.8385 (15)	163
N3—H3A···O1ⁱⁱ	0.86	2.14	2.9871 (15)	171
N3—H3B···O2ⁱⁱⁱ	0.86	2.63	3.0957 (16)	115

Symmetry codes: (i) −x, −y+2, −z; (ii) −x, y+1/2, −z+1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃O₂
M_r	229.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	283
a, b, c (Å)	16.091 (3), 4.7350 (9), 15.776 (3)
β (°)	114.26 (3)
V (Å³)	1095.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.988, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6629, 2324, 1550
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.05
No. of reflections	2324
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

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
O1—H1···N1	0.82	1.83	2.5563 (15)	146.2
N2—H2···O2ⁱ	0.86	2.01	2.8385 (15)	162.5
N3—H3A···O1ⁱⁱ	0.86	2.14	2.9871 (15)	170.6
N3—H3B···O2ⁱⁱⁱ	0.86	2.63	3.0957 (16)	115.2

Symmetry codes: (i) −x, −y+2, −z; (ii) −x, y+1/2, −z+1/2; (iii) x, y−1, z.

Acknowledgements

This work was supported by the Key Project of Science and Technology of Anhui, People's Republic of China (grant No. 08010302218).

References

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