3-Hydr-oxy-N'-(5-hydr-oxy-2-nitro-benzyl-idene)-2-naphthohydrazide.

The mol-ecule of the title compound, C(18)H(13)N(3)O(5), 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, mol-ecules are linked through inter-molecular 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 = 351.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.04

3425 reflections

241 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045279/bh2256sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H13N3O5	F(000) = 728
Mr = 351.31	Dx = 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

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

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(Fo2) + (0.0503P)2 + 0.3232P] where P = (Fo2 + 2Fc2)/3
3425 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.19 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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

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) ; (ii) .