N'-[(2-Hy-droxy-naphthalen-1-yl)methyl-idene]-4-nitro-benzohydrazide.

In the title mol-ecule, C(18)H(13)N(3)O(4), the hy-droxy group is involved in the formation of an intra-molecular O-H⋯N hydrogen bond. The dihedral angle between the planes of the benzene ring and the naphthyl ring system is 9.0 (2)°. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds into chains along the c axis.

Related literature

For recently published crystal structures of hydrazone compounds, see: Horkaew et al. (2011 ▶); Fun et al. (2011 ▶); Su et al. (2011 ▶); Zhi et al. (2011 ▶).

Experimental

Crystal data

C18H13N3O4

M = 335.31

Monoclinic,

a = 11.208 (3) Å

b = 15.432 (3) Å

c = 8.982 (2) Å

β = 90.701 (2)°

V = 1553.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.983

8323 measured reflections

2817 independent reflections

1564 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.127

S = 1.02

2817 reflections

232 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811045685/cv5182sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045685/cv5182Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045685/cv5182Isup3.cml

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

C18H13N3O4	F(000) = 696
Mr = 335.31	Dx = 1.434 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.208 (3) Å	Cell parameters from 1804 reflections
b = 15.432 (3) Å	θ = 2.2–28.2°
c = 8.982 (2) Å	µ = 0.10 mm−1
β = 90.701 (2)°	T = 298 K
V = 1553.4 (6) Å3	Block, yellow
Z = 4	0.20 × 0.20 × 0.17 mm

Bruker SMART 1K CCD area-detector diffractometer	2817 independent reflections
Radiation source: fine-focus sealed tube	1564 reflections with I > 2σ(I)
graphite	Rint = 0.059
ω scan	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.980, Tmax = 0.983	k = −18→16
8323 measured reflections	l = −10→10

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.3228P] where P = (Fo2 + 2Fc2)/3
2817 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.2035 (2)	0.17748 (14)	0.5732 (2)	0.0418 (6)
N2	0.2552 (2)	0.24273 (14)	0.4891 (2)	0.0411 (6)
N3	0.4644 (2)	0.60204 (17)	0.2185 (3)	0.0537 (7)
O1	0.06218 (18)	0.12126 (14)	0.7791 (2)	0.0601 (6)
O2	0.25885 (18)	0.33099 (12)	0.6893 (2)	0.0533 (6)
O3	0.5244 (2)	0.58734 (14)	0.1093 (3)	0.0714 (7)
O4	0.4424 (2)	0.67498 (14)	0.2634 (3)	0.0884 (9)
C1	0.1483 (2)	0.02893 (16)	0.5926 (3)	0.0360 (7)
C2	0.0776 (2)	0.04214 (18)	0.7164 (3)	0.0438 (7)
C3	0.0168 (3)	−0.0276 (2)	0.7829 (3)	0.0561 (9)
H3	−0.0314	−0.0177	0.8648	0.067*
C4	0.0283 (3)	−0.1091 (2)	0.7281 (4)	0.0575 (9)
H4A	−0.0136	−0.1540	0.7724	0.069*
C5	0.1020 (2)	−0.12764 (18)	0.6053 (3)	0.0462 (8)
C6	0.1163 (3)	−0.21292 (19)	0.5488 (4)	0.0634 (10)
H6	0.0747	−0.2584	0.5920	0.076*
C7	0.1890 (3)	−0.2291 (2)	0.4333 (4)	0.0697 (10)
H7	0.1977	−0.2854	0.3981	0.084*
C8	0.2511 (3)	−0.1615 (2)	0.3673 (4)	0.0650 (10)
H8	0.3013	−0.1730	0.2879	0.078*
C9	0.2395 (3)	−0.07840 (17)	0.4173 (3)	0.0504 (8)
H9	0.2825	−0.0344	0.3718	0.060*
C10	0.1632 (2)	−0.05776 (16)	0.5373 (3)	0.0377 (7)
C11	0.2028 (2)	0.10178 (16)	0.5167 (3)	0.0377 (7)
H11	0.2380	0.0929	0.4248	0.045*
C12	0.2780 (2)	0.31916 (16)	0.5567 (3)	0.0377 (7)
C13	0.3284 (2)	0.38988 (16)	0.4623 (3)	0.0341 (6)
C14	0.3080 (2)	0.47496 (16)	0.5080 (3)	0.0416 (7)
H14	0.2641	0.4849	0.5935	0.050*
C15	0.3512 (2)	0.54420 (17)	0.4296 (3)	0.0436 (8)
H15	0.3365	0.6007	0.4604	0.052*
C16	0.4170 (2)	0.52799 (16)	0.3039 (3)	0.0386 (7)
C17	0.4401 (2)	0.44479 (17)	0.2556 (3)	0.0431 (7)
H17	0.4845	0.4355	0.1702	0.052*
C18	0.3963 (2)	0.37526 (17)	0.3363 (3)	0.0418 (7)
H18	0.4124	0.3189	0.3060	0.050*
H2	0.263 (3)	0.2326 (19)	0.3912 (13)	0.080*
H1	0.100 (3)	0.1599 (15)	0.730 (3)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0548 (16)	0.0325 (13)	0.0381 (15)	−0.0026 (11)	0.0055 (12)	0.0056 (12)
N2	0.0596 (16)	0.0313 (13)	0.0326 (14)	−0.0049 (11)	0.0078 (13)	0.0009 (12)
N3	0.0514 (17)	0.0484 (18)	0.061 (2)	−0.0082 (13)	0.0051 (15)	0.0071 (15)
O1	0.0646 (16)	0.0614 (15)	0.0547 (16)	0.0077 (12)	0.0191 (12)	−0.0034 (12)
O2	0.0846 (16)	0.0478 (12)	0.0279 (12)	−0.0042 (10)	0.0145 (11)	−0.0027 (9)
O3	0.0816 (18)	0.0724 (16)	0.0608 (16)	−0.0184 (13)	0.0259 (14)	0.0057 (13)
O4	0.106 (2)	0.0380 (13)	0.122 (2)	0.0020 (13)	0.0465 (17)	0.0116 (14)
C1	0.0366 (16)	0.0398 (17)	0.0317 (17)	0.0017 (13)	0.0015 (14)	0.0060 (13)
C2	0.0439 (18)	0.0465 (18)	0.0409 (19)	0.0049 (14)	0.0008 (16)	0.0026 (15)
C3	0.047 (2)	0.079 (2)	0.043 (2)	−0.0017 (17)	0.0121 (16)	0.0169 (18)
C4	0.053 (2)	0.052 (2)	0.067 (2)	−0.0131 (16)	−0.0026 (19)	0.0260 (18)
C5	0.0410 (18)	0.0447 (19)	0.053 (2)	−0.0038 (14)	−0.0023 (16)	0.0124 (16)
C6	0.068 (2)	0.037 (2)	0.085 (3)	−0.0094 (16)	−0.012 (2)	0.0134 (19)
C7	0.081 (3)	0.038 (2)	0.091 (3)	0.0013 (18)	−0.010 (2)	−0.006 (2)
C8	0.075 (2)	0.048 (2)	0.072 (3)	0.0029 (18)	0.005 (2)	−0.0115 (18)
C9	0.057 (2)	0.0370 (18)	0.058 (2)	−0.0003 (14)	0.0067 (17)	0.0002 (15)
C10	0.0387 (17)	0.0341 (16)	0.0402 (18)	−0.0008 (13)	−0.0045 (14)	0.0076 (14)
C11	0.0428 (17)	0.0367 (17)	0.0338 (17)	0.0012 (13)	0.0065 (13)	0.0058 (14)
C12	0.0427 (17)	0.0377 (17)	0.0329 (18)	0.0023 (13)	0.0033 (14)	−0.0011 (14)
C13	0.0376 (16)	0.0339 (16)	0.0307 (17)	−0.0016 (13)	0.0018 (13)	−0.0022 (13)
C14	0.0487 (18)	0.0394 (17)	0.0370 (18)	0.0017 (13)	0.0126 (14)	−0.0052 (14)
C15	0.0482 (18)	0.0344 (16)	0.048 (2)	0.0036 (13)	0.0071 (16)	−0.0034 (14)
C16	0.0380 (16)	0.0349 (16)	0.0428 (18)	−0.0053 (13)	0.0020 (14)	0.0011 (14)
C17	0.0462 (18)	0.0490 (18)	0.0344 (18)	−0.0047 (14)	0.0109 (14)	−0.0030 (15)
C18	0.0478 (18)	0.0369 (16)	0.0408 (19)	−0.0023 (13)	0.0053 (15)	−0.0082 (14)

N1—C11	1.274 (3)	C6—C7	1.351 (4)
N1—N2	1.390 (3)	C6—H6	0.9300
N2—C12	1.350 (3)	C7—C8	1.392 (4)
N2—H2	0.898 (10)	C7—H7	0.9300
N3—O3	1.218 (3)	C8—C9	1.365 (4)
N3—O4	1.222 (3)	C8—H8	0.9300
N3—C16	1.479 (3)	C9—C10	1.420 (4)
O1—C2	1.357 (3)	C9—H9	0.9300
O1—H1	0.859 (10)	C11—H11	0.9300
O2—C12	1.227 (3)	C12—C13	1.496 (3)
C1—C2	1.388 (4)	C13—C18	1.391 (3)
C1—C10	1.437 (3)	C13—C14	1.395 (3)
C1—C11	1.453 (3)	C14—C15	1.371 (3)
C2—C3	1.411 (4)	C14—H14	0.9300
C3—C4	1.357 (4)	C15—C16	1.379 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.415 (4)	C16—C17	1.381 (3)
C4—H4A	0.9300	C17—C18	1.388 (3)
C5—C10	1.420 (3)	C17—H17	0.9300
C5—C6	1.420 (4)	C18—H18	0.9300
C11—N1—N2	116.7 (2)	C7—C8—H8	119.5
C12—N2—N1	117.8 (2)	C8—C9—C10	121.4 (3)
C12—N2—H2	125 (2)	C8—C9—H9	119.3
N1—N2—H2	117 (2)	C10—C9—H9	119.3
O3—N3—O4	123.6 (3)	C5—C10—C9	117.0 (2)
O3—N3—C16	118.7 (3)	C5—C10—C1	120.0 (3)
O4—N3—C16	117.7 (3)	C9—C10—C1	123.0 (2)
C2—O1—H1	110 (2)	N1—C11—C1	121.6 (3)
C2—C1—C10	118.9 (2)	N1—C11—H11	119.2
C2—C1—C11	120.6 (2)	C1—C11—H11	119.2
C10—C1—C11	120.5 (2)	O2—C12—N2	122.2 (2)
O1—C2—C1	122.8 (3)	O2—C12—C13	120.9 (2)
O1—C2—C3	116.5 (3)	N2—C12—C13	117.0 (2)
C1—C2—C3	120.7 (3)	C18—C13—C14	119.0 (2)
C4—C3—C2	120.3 (3)	C18—C13—C12	123.8 (2)
C4—C3—H3	119.9	C14—C13—C12	117.1 (2)
C2—C3—H3	119.9	C15—C14—C13	121.5 (3)
C3—C4—C5	122.0 (3)	C15—C14—H14	119.3
C3—C4—H4A	119.0	C13—C14—H14	119.3
C5—C4—H4A	119.0	C14—C15—C16	118.3 (2)
C4—C5—C10	118.1 (3)	C14—C15—H15	120.8
C4—C5—C6	122.4 (3)	C16—C15—H15	120.8
C10—C5—C6	119.5 (3)	C15—C16—C17	122.0 (2)
C7—C6—C5	121.2 (3)	C15—C16—N3	118.9 (3)
C7—C6—H6	119.4	C17—C16—N3	119.0 (3)
C5—C6—H6	119.4	C16—C17—C18	119.1 (3)
C6—C7—C8	119.9 (3)	C16—C17—H17	120.5
C6—C7—H7	120.1	C18—C17—H17	120.5
C8—C7—H7	120.1	C17—C18—C13	120.0 (2)
C9—C8—C7	120.9 (3)	C17—C18—H18	120.0
C9—C8—H8	119.5	C13—C18—H18	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (1)	1.85 (2)	2.599 (3)	144 (3)
N2—H2···O2i	0.90 (1)	2.06 (1)	2.923 (3)	160 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.86 (1)	1.85 (2)	2.599 (3)	144 (3)
N2—H2⋯O2i	0.90 (1)	2.06 (1)	2.923 (3)	160 (3)

Symmetry code: (i) .