3-Hydr­oxy-N′-(5-hydr­oxy-2-nitro­benzyl­idene)-2-naphthohydrazide

Yang, D.-S.

doi:10.1107/S1600536809045279

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2978

doi:10.1107/S1600536809045279

Open

access

3-Hydroxy-N′-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide

De-Suo Yang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People's Republic of China
^*Correspondence e-mail: desuoyang@yahoo.com.cn

(Received 21 October 2009; accepted 29 October 2009; online 4 November 2009)

The molecule of the title compound, C₁₈H₁₃N₃O₅, displays an E configuration with respect to the C=N double bond. The dihedral angle between the benzene ring and the naphthyl system is 1.1 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological and structural chemistry of hydrazone compounds, see: Avaji et al. (2009 ); Charkoudian et al. (2007 ); Cukurovali et al. (2006 ). For related structures, see: Yang (2008a ,b ,c ,d ,e, 2007a ,b ,c ); Yang & Guo (2006 ).

Experimental

Crystal data

C₁₈H₁₃N₃O₅
M_r = 351.31
Monoclinic, P 2₁ /n
a = 10.1588 (3) Å
b = 8.2562 (2) Å
c = 19.5268 (5) Å
β = 104.867 (1)°
V = 1582.95 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.978
9168 measured reflections
3425 independent reflections
2436 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.04
3425 reflections
241 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 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
O2—H2⋯O1	0.82	1.88	2.5987 (18)	146
N1—H1⋯O4ⁱ	0.898 (9)	2.144 (10)	3.0361 (19)	172.8 (18)
O5—H5⋯O1ⁱⁱ	0.82	1.88	2.6889 (17)	168
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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/S1600536809045279/bh2256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045279/bh2256Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have been of great interest for their versatile biological and structural chemistry (Avaji et al., 2009; Charkoudian et al., 2007; Cukurovali et al., 2006). Recently, we have reported a few hydrazone compounds (Yang, 2008a,b,c,d,e, 2007a,b,c; Yang & Guo, 2006). As a further investigation of this work, the crystal structure of the title new hydrazone compound is reported.

In the title compound (Fig. 1), the molecule displays an E configuration with respect to the C═N double bond. The C13···C18 benzene ring forms dihedral angles of 28.6 (2) and 1.1 (2)°, respectively, with the O3—N3—O4 nitro group and the C1···C10 naphthyl ring. All bond lengths are within normal ranges. The C12═N2 bond length of 1.266 (2) Å, conforms to the value for a formal double bond. The bond length of 1.341 (2) Å between atoms C11 and N1 is intermediate between a C—N single bond and a C═N double bond, because of conjugation effects in the molecule.

In the crystal structure, molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).

Related literature top

For the biological and structural chemistry of hydrazone compounds, see: Avaji et al. (2009); Charkoudian et al. (2007); Cukurovali et al. (2006). For related structures, see: Yang (2008a,b,c,d,e, 2007a,b,c); Yang & Guo (2006).

Experimental top

5-Hydroxy-2-nitrobenzaldehyde (0.1 mmol, 16.7 mg) and 3-hydroxy-2-naphthohydrazide (0.1 mmol, 20.2 mg) were dissolved in CHCl₃ (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 3 days, at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as a dashed line.
	Fig. 2. Molecular packing as viewed along the b axis. Hydrogen bonds are shown as dashed lines.

3-Hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide top

Crystal data top

C₁₈H₁₃N₃O₅	F(000) = 728
M_r = 351.31	D_x = 1.474 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2463 reflections
a = 10.1588 (3) Å	θ = 2.5–26.6°
b = 8.2562 (2) Å	µ = 0.11 mm⁻¹
c = 19.5268 (5) Å	T = 298 K
β = 104.867 (1)°	Block, colorless
V = 1582.95 (7) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3425 independent reflections
Radiation source: fine-focus sealed tube	2436 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.975, T_max = 0.978	k = −10→10
9168 measured reflections	l = −24→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0503P)² + 0.3232P] where P = (F_o² + 2F_c²)/3
3425 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³
0 constraints

Crystal data top

C₁₈H₁₃N₃O₅	V = 1582.95 (7) Å³
M_r = 351.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1588 (3) Å	µ = 0.11 mm⁻¹
b = 8.2562 (2) Å	T = 298 K
c = 19.5268 (5) Å	0.23 × 0.20 × 0.20 mm
β = 104.867 (1)°

Data collection top

Bruker SMART CCD diffractometer	3425 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2436 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.978	R_int = 0.028
9168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.19 e Å⁻³
3425 reflections	Δρ_min = −0.19 e Å⁻³
241 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.88109 (14)	0.92607 (17)	0.05530 (7)	0.0462 (4)
N2	1.00455 (13)	0.88709 (16)	0.10140 (7)	0.0446 (3)
N3	1.20940 (14)	0.48961 (18)	0.04801 (7)	0.0461 (3)
O1	0.86564 (13)	1.16125 (15)	0.11112 (6)	0.0575 (4)
O2	0.63397 (15)	1.31345 (18)	0.08033 (7)	0.0689 (4)
H2	0.7084	1.2854	0.1052	0.103*
O3	1.13711 (14)	0.56430 (16)	−0.00173 (6)	0.0612 (4)
O4	1.24674 (14)	0.34954 (16)	0.04217 (7)	0.0695 (4)
O5	1.38574 (15)	0.75885 (19)	0.31532 (6)	0.0721 (4)
H5	1.4565	0.7160	0.3377	0.108*
C1	0.69456 (16)	1.10569 (19)	0.00579 (8)	0.0407 (4)
C2	0.60609 (17)	1.2299 (2)	0.01840 (9)	0.0485 (4)
C3	0.49048 (18)	1.2674 (3)	−0.03235 (10)	0.0601 (5)
H3	0.4332	1.3482	−0.0234	0.072*
C4	0.45611 (17)	1.1865 (3)	−0.09781 (10)	0.0582 (5)
C5	0.3359 (2)	1.2237 (3)	−0.15133 (13)	0.0833 (8)
H5A	0.2756	1.3013	−0.1428	0.100*
C6	0.3090 (3)	1.1465 (4)	−0.21477 (15)	0.1025 (11)
H6	0.2299	1.1717	−0.2493	0.123*
C7	0.3980 (3)	1.0294 (3)	−0.22928 (13)	0.1001 (10)
H7	0.3782	0.9787	−0.2733	0.120*
C8	0.5134 (2)	0.9896 (3)	−0.17908 (11)	0.0769 (7)
H8	0.5721	0.9116	−0.1889	0.092*
C9	0.54456 (19)	1.0664 (2)	−0.11211 (9)	0.0541 (5)
C10	0.66309 (18)	1.0299 (2)	−0.05915 (9)	0.0477 (4)
H10	0.7224	0.9519	−0.0683	0.057*
C11	0.81986 (16)	1.06728 (19)	0.06131 (8)	0.0417 (4)
C12	1.04643 (17)	0.7455 (2)	0.09371 (9)	0.0468 (4)
H12	0.9935	0.6774	0.0596	0.056*
C13	1.17752 (16)	0.68736 (18)	0.13789 (8)	0.0398 (4)
C14	1.25482 (16)	0.56598 (18)	0.11681 (8)	0.0381 (3)
C15	1.37767 (16)	0.51385 (19)	0.16009 (9)	0.0429 (4)
H15	1.4276	0.4342	0.1443	0.051*
C16	1.42572 (16)	0.5796 (2)	0.22626 (8)	0.0440 (4)
H16	1.5094	0.5471	0.2550	0.053*
C17	1.34847 (18)	0.6951 (2)	0.24990 (8)	0.0466 (4)
C18	1.22688 (17)	0.7487 (2)	0.20549 (8)	0.0481 (4)
H18	1.1772	0.8280	0.2216	0.058*
H1	0.8395 (18)	0.8513 (19)	0.0237 (8)	0.066 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0433 (8)	0.0423 (8)	0.0426 (8)	0.0066 (6)	−0.0077 (6)	−0.0034 (6)
N2	0.0416 (7)	0.0449 (8)	0.0399 (7)	0.0064 (6)	−0.0033 (6)	0.0013 (6)
N3	0.0441 (8)	0.0456 (8)	0.0486 (8)	−0.0067 (6)	0.0117 (7)	−0.0072 (7)
O1	0.0632 (8)	0.0469 (7)	0.0482 (7)	0.0076 (6)	−0.0119 (6)	−0.0087 (6)
O2	0.0754 (10)	0.0743 (10)	0.0563 (8)	0.0261 (8)	0.0159 (7)	−0.0026 (7)
O3	0.0687 (9)	0.0642 (9)	0.0433 (7)	−0.0101 (7)	0.0007 (6)	−0.0002 (6)
O4	0.0683 (9)	0.0559 (8)	0.0786 (9)	0.0076 (7)	0.0085 (7)	−0.0274 (7)
O5	0.0725 (10)	0.0899 (11)	0.0412 (7)	0.0308 (8)	−0.0088 (6)	−0.0124 (7)
C1	0.0390 (8)	0.0370 (8)	0.0416 (8)	−0.0019 (7)	0.0022 (7)	0.0075 (7)
C2	0.0475 (10)	0.0517 (10)	0.0469 (10)	0.0047 (8)	0.0133 (8)	0.0101 (8)
C3	0.0431 (10)	0.0710 (13)	0.0687 (13)	0.0150 (9)	0.0189 (9)	0.0243 (11)
C4	0.0378 (9)	0.0711 (13)	0.0591 (12)	−0.0109 (9)	0.0004 (8)	0.0282 (10)
C5	0.0427 (11)	0.1106 (19)	0.0836 (16)	−0.0086 (12)	−0.0074 (11)	0.0461 (15)
C6	0.0652 (15)	0.120 (2)	0.0910 (19)	−0.0332 (16)	−0.0366 (14)	0.0452 (18)
C7	0.113 (2)	0.0834 (18)	0.0686 (15)	−0.0412 (17)	−0.0400 (15)	0.0161 (13)
C8	0.0945 (16)	0.0613 (13)	0.0542 (12)	−0.0199 (12)	−0.0187 (11)	0.0049 (10)
C9	0.0536 (11)	0.0486 (10)	0.0485 (10)	−0.0154 (9)	−0.0080 (8)	0.0144 (8)
C10	0.0518 (10)	0.0375 (8)	0.0459 (9)	−0.0020 (8)	−0.0022 (8)	0.0045 (7)
C11	0.0437 (9)	0.0382 (8)	0.0384 (8)	0.0000 (7)	0.0016 (7)	0.0026 (7)
C12	0.0455 (9)	0.0440 (9)	0.0434 (9)	0.0023 (8)	−0.0022 (7)	−0.0052 (7)
C13	0.0403 (8)	0.0366 (8)	0.0387 (8)	0.0020 (7)	0.0031 (7)	0.0030 (7)
C14	0.0422 (8)	0.0333 (8)	0.0376 (8)	−0.0044 (7)	0.0082 (7)	0.0001 (6)
C15	0.0438 (9)	0.0363 (8)	0.0497 (9)	0.0043 (7)	0.0141 (8)	0.0035 (7)
C16	0.0409 (9)	0.0443 (9)	0.0430 (9)	0.0060 (7)	0.0038 (7)	0.0090 (7)
C17	0.0506 (10)	0.0494 (10)	0.0350 (8)	0.0053 (8)	0.0022 (7)	0.0009 (7)
C18	0.0499 (10)	0.0462 (9)	0.0436 (9)	0.0140 (8)	0.0037 (8)	−0.0029 (7)

Geometric parameters (Å, º) top

N1—C11	1.341 (2)	C5—H5A	0.9300
N1—N2	1.3812 (18)	C6—C7	1.402 (4)
N1—H1	0.898 (9)	C6—H6	0.9300
N2—C12	1.266 (2)	C7—C8	1.362 (3)
N3—O3	1.2235 (18)	C7—H7	0.9300
N3—O4	1.2315 (18)	C8—C9	1.414 (3)
N3—C14	1.448 (2)	C8—H8	0.9300
O1—C11	1.2378 (18)	C9—C10	1.404 (2)
O2—C2	1.357 (2)	C10—H10	0.9300
O2—H2	0.8200	C12—C13	1.469 (2)
O5—C17	1.343 (2)	C12—H12	0.9300
O5—H5	0.8200	C13—C18	1.382 (2)
C1—C10	1.376 (2)	C13—C14	1.399 (2)
C1—C2	1.426 (2)	C14—C15	1.384 (2)
C1—C11	1.479 (2)	C15—C16	1.371 (2)
C2—C3	1.364 (2)	C15—H15	0.9300
C3—C4	1.405 (3)	C16—C17	1.387 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C9	1.414 (3)	C17—C18	1.387 (2)
C4—C5	1.422 (3)	C18—H18	0.9300
C5—C6	1.357 (4)

C11—N1—N2	120.64 (13)	C9—C8—H8	119.8
C11—N1—H1	120.7 (13)	C10—C9—C4	118.26 (17)
N2—N1—H1	118.4 (13)	C10—C9—C8	122.1 (2)
C12—N2—N1	114.48 (14)	C4—C9—C8	119.63 (18)
O3—N3—O4	122.43 (14)	C1—C10—C9	122.28 (17)
O3—N3—C14	120.03 (14)	C1—C10—H10	118.9
O4—N3—C14	117.54 (14)	C9—C10—H10	118.9
C2—O2—H2	109.5	O1—C11—N1	121.64 (14)
C17—O5—H5	109.5	O1—C11—C1	121.38 (15)
C10—C1—C2	118.58 (15)	N1—C11—C1	116.98 (14)
C10—C1—C11	122.05 (15)	N2—C12—C13	120.90 (15)
C2—C1—C11	119.31 (14)	N2—C12—H12	119.5
O2—C2—C3	118.43 (17)	C13—C12—H12	119.5
O2—C2—C1	121.50 (15)	C18—C13—C14	116.75 (14)
C3—C2—C1	120.07 (17)	C18—C13—C12	119.55 (15)
C2—C3—C4	121.34 (18)	C14—C13—C12	123.64 (14)
C2—C3—H3	119.3	C15—C14—C13	121.96 (14)
C4—C3—H3	119.3	C15—C14—N3	116.99 (14)
C3—C4—C9	119.42 (16)	C13—C14—N3	121.04 (14)
C3—C4—C5	122.1 (2)	C16—C15—C14	119.98 (15)
C9—C4—C5	118.4 (2)	C16—C15—H15	120.0
C6—C5—C4	120.2 (3)	C14—C15—H15	120.0
C6—C5—H5A	119.9	C15—C16—C17	119.39 (15)
C4—C5—H5A	119.9	C15—C16—H16	120.3
C5—C6—C7	121.3 (2)	C17—C16—H16	120.3
C5—C6—H6	119.4	O5—C17—C16	122.72 (15)
C7—C6—H6	119.4	O5—C17—C18	117.25 (16)
C8—C7—C6	120.1 (3)	C16—C17—C18	120.03 (15)
C8—C7—H7	119.9	C13—C18—C17	121.79 (16)
C6—C7—H7	119.9	C13—C18—H18	119.1
C7—C8—C9	120.3 (3)	C17—C18—H18	119.1
C7—C8—H8	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.88	2.5987 (18)	146
N1—H1···O4ⁱ	0.90 (1)	2.14 (1)	3.0361 (19)	173 (2)
O5—H5···O1ⁱⁱ	0.82	1.88	2.6889 (17)	168

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+5/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃N₃O₅
M_r	351.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.1588 (3), 8.2562 (2), 19.5268 (5)
β (°)	104.867 (1)
V (Å³)	1582.95 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	9168, 3425, 2436
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.04
No. of reflections	3425
No. of parameters	241
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)	0.19, −0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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···O1	0.82	1.88	2.5987 (18)	146.3
N1—H1···O4ⁱ	0.898 (9)	2.144 (10)	3.0361 (19)	172.8 (18)
O5—H5···O1ⁱⁱ	0.82	1.88	2.6889 (17)	168.0

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+5/2, y−1/2, −z+1/2.

Acknowledgements

The author acknowledges Baoji University of Arts and Sciences for support.

References

Avaji, P. G., Vinod Kumar, C. H., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552–3559. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Charkoudian, L. K., Pham, D. M., Kwon, A. M., Vangeloff, A. D. & Franz, K. J. (2007). J. Chem. Soc. Dalton Trans. pp. 5031–5042. CrossRef Google Scholar
Cukurovali, A., Yilmaz, I., Gur, S. & Kazaz, C. (2006). Eur. J. Med. Chem. 41, 201–207. Web of Science CrossRef PubMed CAS 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
Yang, D.-S. (2007a). J. Chem. Crystallogr. 37, 343–348. Web of Science CSD CrossRef CAS Google Scholar
Yang, D.-S. (2007b). Acta Cryst. E63, o3738. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. (2007c). Acta Cryst. E63, o3739. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. (2008a). Acta Cryst. E64, o1758. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. (2008b). Acta Cryst. E64, o1759. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. (2008c). Acta Cryst. E64, o1849. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. (2008d). Acta Cryst. E64, o1850. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. & Guo, J.-B. (2006). Acta Cryst. E62, o4414–o4415. Web of Science CSD CrossRef IUCr Journals Google Scholar