N'-(2-Hy-droxy-1-naphth-yl-methylidene)-3-meth-oxy-benzohydrazide.

In the title compound, C(19)H(16)N(2)O(3), the dihedral angle between the naphthalene ring system and the benzene ring is 19.8 (3)°. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. In the crystal, mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazone compounds, see: Arunkumar et al. (2006 ▶); Saxena et al. (2008 ▶); Zia-ur-Rehman et al. (2009 ▶); Galal et al. (2009 ▶); Bordoloi et al. (2009 ▶). For similar hydrazone compounds, see: Han et al. (2010 ▶); Wang et al. (2010 ▶); Qiao et al. (2010 ▶); Suleiman Gwaram et al. (2010 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

C19H16N2O3

M = 320.34

Monoclinic,

a = 7.1700 (15) Å

b = 31.174 (7) Å

c = 7.4669 (16) Å

β = 109.746 (12)°

V = 1570.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.984

9232 measured reflections

3405 independent reflections

1839 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.141

S = 0.92

3405 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.23 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022026/rz2461sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022026/rz2461Isup2.hkl

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

C19H16N2O3	F(000) = 672
Mr = 320.34	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1460 reflections
a = 7.1700 (15) Å	θ = 2.5–24.0°
b = 31.174 (7) Å	µ = 0.09 mm−1
c = 7.4669 (16) Å	T = 298 K
β = 109.746 (12)°	Block, colourless
V = 1570.9 (6) Å3	0.18 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
graphite	Rint = 0.093
ω scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.984, Tmax = 0.984	k = −39→35
9232 measured reflections	l = −7→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3
3405 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.23 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	0.9564 (3)	0.21280 (5)	0.6283 (3)	0.0368 (5)
N2	0.9265 (3)	0.24056 (6)	0.4765 (3)	0.0377 (5)
O1	1.0227 (3)	0.19610 (5)	0.9820 (2)	0.0522 (5)
H1	1.0193	0.2108	0.8900	0.078*
O2	1.1086 (2)	0.29306 (4)	0.6668 (2)	0.0446 (4)
O3	0.8581 (3)	0.42263 (5)	0.2180 (3)	0.0610 (5)
C1	0.9067 (3)	0.14315 (6)	0.7351 (3)	0.0325 (5)
C2	0.9652 (3)	0.15572 (7)	0.9238 (3)	0.0374 (5)
C3	0.9684 (4)	0.12616 (8)	1.0675 (3)	0.0448 (6)
H3	1.0045	0.1353	1.1932	0.054*
C4	0.9194 (4)	0.08463 (8)	1.0244 (4)	0.0465 (6)
H4	0.9231	0.0656	1.1215	0.056*
C5	0.8625 (3)	0.06948 (7)	0.8351 (3)	0.0385 (6)
C6	0.8142 (4)	0.02588 (8)	0.7898 (4)	0.0512 (7)
H6	0.8181	0.0068	0.8867	0.061*
C7	0.7624 (4)	0.01126 (8)	0.6091 (5)	0.0632 (8)
H7	0.7330	−0.0176	0.5820	0.076*
C8	0.7539 (5)	0.04030 (8)	0.4638 (4)	0.0667 (8)
H8	0.7171	0.0305	0.3390	0.080*
C9	0.7981 (4)	0.08248 (8)	0.5010 (4)	0.0521 (7)
H9	0.7913	0.1009	0.4010	0.063*
C10	0.8543 (3)	0.09898 (7)	0.6881 (3)	0.0351 (5)
C11	0.8922 (3)	0.17435 (7)	0.5871 (3)	0.0358 (5)
H11	0.8354	0.1664	0.4601	0.043*
C12	1.0051 (3)	0.28023 (7)	0.5079 (3)	0.0330 (5)
C13	0.9564 (3)	0.30824 (7)	0.3373 (3)	0.0324 (5)
C14	0.9349 (3)	0.35181 (7)	0.3628 (3)	0.0363 (5)
H14	0.9528	0.3624	0.4839	0.044*
C15	0.8871 (3)	0.37955 (7)	0.2097 (4)	0.0417 (6)
C16	0.8640 (4)	0.36340 (9)	0.0300 (4)	0.0530 (7)
H16	0.8325	0.3819	−0.0736	0.064*
C17	0.8871 (4)	0.32039 (9)	0.0040 (4)	0.0535 (7)
H17	0.8726	0.3100	−0.1167	0.064*
C18	0.9320 (3)	0.29230 (7)	0.1567 (3)	0.0417 (6)
H18	0.9457	0.2631	0.1387	0.050*
C19	0.8793 (5)	0.44027 (8)	0.3982 (5)	0.0690 (9)
H19A	0.7877	0.4266	0.4486	0.104*
H19B	0.8525	0.4705	0.3853	0.104*
H19C	1.0122	0.4357	0.4830	0.104*
H2	0.836 (3)	0.2332 (9)	0.363 (2)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0382 (11)	0.0332 (10)	0.0349 (11)	0.0007 (9)	0.0070 (9)	0.0046 (9)
N2	0.0449 (12)	0.0303 (10)	0.0301 (11)	−0.0025 (9)	0.0024 (9)	0.0034 (9)
O1	0.0689 (12)	0.0450 (10)	0.0397 (10)	−0.0084 (10)	0.0143 (10)	−0.0079 (8)
O2	0.0511 (10)	0.0396 (9)	0.0309 (9)	−0.0023 (8)	−0.0020 (8)	−0.0008 (7)
O3	0.0633 (13)	0.0403 (10)	0.0735 (14)	0.0055 (9)	0.0154 (11)	0.0180 (10)
C1	0.0297 (12)	0.0359 (12)	0.0311 (13)	0.0015 (10)	0.0091 (10)	0.0030 (10)
C2	0.0353 (13)	0.0369 (13)	0.0390 (14)	0.0017 (11)	0.0114 (11)	−0.0016 (11)
C3	0.0468 (15)	0.0558 (16)	0.0301 (13)	0.0031 (13)	0.0108 (12)	0.0026 (12)
C4	0.0460 (15)	0.0502 (15)	0.0443 (15)	0.0037 (13)	0.0167 (12)	0.0151 (13)
C5	0.0344 (13)	0.0353 (12)	0.0469 (15)	0.0032 (11)	0.0150 (11)	0.0058 (11)
C6	0.0495 (16)	0.0413 (14)	0.0623 (18)	0.0014 (13)	0.0184 (14)	0.0107 (14)
C7	0.071 (2)	0.0338 (14)	0.082 (2)	−0.0066 (13)	0.0229 (18)	−0.0013 (15)
C8	0.093 (2)	0.0472 (16)	0.0570 (19)	−0.0146 (16)	0.0211 (18)	−0.0146 (15)
C9	0.0714 (19)	0.0417 (14)	0.0436 (15)	−0.0093 (13)	0.0199 (14)	−0.0033 (12)
C10	0.0328 (12)	0.0344 (12)	0.0371 (13)	0.0016 (10)	0.0105 (11)	0.0010 (11)
C11	0.0370 (13)	0.0371 (12)	0.0296 (12)	0.0000 (11)	0.0065 (10)	−0.0002 (10)
C12	0.0326 (12)	0.0318 (12)	0.0305 (12)	0.0020 (10)	0.0054 (10)	−0.0011 (10)
C13	0.0285 (11)	0.0363 (12)	0.0282 (12)	−0.0034 (10)	0.0042 (9)	−0.0006 (10)
C14	0.0327 (12)	0.0370 (12)	0.0368 (13)	−0.0025 (10)	0.0084 (10)	−0.0009 (11)
C15	0.0333 (13)	0.0387 (13)	0.0481 (15)	−0.0008 (11)	0.0073 (11)	0.0112 (12)
C16	0.0485 (16)	0.0640 (18)	0.0408 (16)	−0.0083 (14)	0.0075 (12)	0.0168 (14)
C17	0.0556 (17)	0.0742 (19)	0.0307 (14)	−0.0132 (15)	0.0147 (12)	−0.0008 (14)
C18	0.0440 (14)	0.0447 (13)	0.0358 (14)	−0.0041 (12)	0.0126 (11)	−0.0034 (11)
C19	0.074 (2)	0.0426 (15)	0.100 (3)	0.0077 (15)	0.042 (2)	0.0013 (16)

N1—C11	1.284 (3)	C7—C8	1.398 (4)
N1—N2	1.384 (2)	C7—H7	0.9300
N2—C12	1.346 (3)	C8—C9	1.359 (3)
N2—H2	0.905 (10)	C8—H8	0.9300
O1—C2	1.350 (2)	C9—C10	1.414 (3)
O1—H1	0.8200	C9—H9	0.9300
O2—C12	1.235 (3)	C11—H11	0.9300
O3—C15	1.364 (3)	C12—C13	1.485 (3)
O3—C19	1.413 (3)	C13—C14	1.387 (3)
C1—C2	1.384 (3)	C13—C18	1.391 (3)
C1—C10	1.439 (3)	C14—C15	1.381 (3)
C1—C11	1.450 (3)	C14—H14	0.9300
C2—C3	1.408 (3)	C15—C16	1.390 (3)
C3—C4	1.351 (3)	C16—C17	1.373 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.414 (3)	C17—C18	1.387 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.415 (3)	C18—H18	0.9300
C5—C10	1.418 (3)	C19—H19A	0.9600
C6—C7	1.351 (4)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C11—N1—N2	116.33 (18)	C9—C10—C5	116.9 (2)
C12—N2—N1	119.46 (18)	C9—C10—C1	123.6 (2)
C12—N2—H2	121.4 (18)	C5—C10—C1	119.5 (2)
N1—N2—H2	118.1 (18)	N1—C11—C1	121.1 (2)
C2—O1—H1	109.5	N1—C11—H11	119.5
C15—O3—C19	117.2 (2)	C1—C11—H11	119.5
C2—C1—C10	118.92 (19)	O2—C12—N2	123.04 (19)
C2—C1—C11	120.4 (2)	O2—C12—C13	121.64 (19)
C10—C1—C11	120.69 (19)	N2—C12—C13	115.32 (19)
O1—C2—C1	123.1 (2)	C14—C13—C18	120.0 (2)
O1—C2—C3	116.1 (2)	C14—C13—C12	117.57 (19)
C1—C2—C3	120.8 (2)	C18—C13—C12	122.48 (19)
C4—C3—C2	120.6 (2)	C15—C14—C13	120.5 (2)
C4—C3—H3	119.7	C15—C14—H14	119.7
C2—C3—H3	119.7	C13—C14—H14	119.7
C3—C4—C5	121.5 (2)	O3—C15—C14	125.3 (2)
C3—C4—H4	119.3	O3—C15—C16	115.5 (2)
C5—C4—H4	119.3	C14—C15—C16	119.2 (2)
C4—C5—C6	121.6 (2)	C17—C16—C15	120.6 (2)
C4—C5—C10	118.7 (2)	C17—C16—H16	119.7
C6—C5—C10	119.7 (2)	C15—C16—H16	119.7
C7—C6—C5	121.7 (2)	C16—C17—C18	120.4 (2)
C7—C6—H6	119.2	C16—C17—H17	119.8
C5—C6—H6	119.2	C18—C17—H17	119.8
C6—C7—C8	118.8 (2)	C17—C18—C13	119.3 (2)
C6—C7—H7	120.6	C17—C18—H18	120.4
C8—C7—H7	120.6	C13—C18—H18	120.4
C9—C8—C7	121.5 (3)	O3—C19—H19A	109.5
C9—C8—H8	119.3	O3—C19—H19B	109.5
C7—C8—H8	119.3	H19A—C19—H19B	109.5
C8—C9—C10	121.5 (2)	O3—C19—H19C	109.5
C8—C9—H9	119.2	H19A—C19—H19C	109.5
C10—C9—H9	119.2	H19B—C19—H19C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.91 (1)	1.97 (1)	2.842 (3)	163 (2)
O1—H1···N1	0.82	1.85	2.574 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.91 (1)	1.97 (1)	2.842 (3)	163 (2)
O1—H1⋯N1	0.82	1.85	2.574 (2)	146

Symmetry code: (i) .