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

In the title compound, C(19)H(16)N(2)O(2), the benzene ring and the naphthyl ring system form a dihedral angle of 8.7 (3)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming C(4) chains propagating in [001].

Related literature

For hydrazones we have reported previously and background references, see: Liu & You (2010a ▶,b ▶,c ▶); Liu & Wang (2010a ▶,b ▶). For a related structure, see: Cao (2009 ▶).

Experimental

Crystal data

C19H16N2O2

M = 304.34

Monoclinic,

a = 11.014 (2) Å

b = 15.487 (2) Å

c = 9.150 (1) Å

β = 93.503 (3)°

V = 1557.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.983, T max = 0.987

12464 measured reflections

3335 independent reflections

1515 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.192

S = 0.93

3335 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101035X/hb5818sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101035X/hb5818Isup2.hkl

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

C19H16N2O2	F(000) = 640
Mr = 304.34	Dx = 1.298 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1270 reflections
a = 11.014 (2) Å	θ = 2.3–26.4°
b = 15.487 (2) Å	µ = 0.09 mm−1
c = 9.150 (1) Å	T = 298 K
β = 93.503 (3)°	Block, colourless
V = 1557.8 (4) Å3	0.20 × 0.17 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	3335 independent reflections
Radiation source: fine-focus sealed tube	1515 reflections with I > 2σ(I)
graphite	Rint = 0.065
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→13
Tmin = 0.983, Tmax = 0.987	k = −19→19
12464 measured reflections	l = −11→11

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0921P)2] where P = (Fo2 + 2Fc2)/3
3335 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6996 (2)	0.17460 (14)	−0.0689 (2)	0.0519 (6)
N2	0.7488 (2)	0.24189 (14)	0.0157 (2)	0.0525 (7)
O1	0.5593 (2)	0.11437 (14)	−0.2818 (2)	0.0706 (7)
H1	0.5958	0.1516	−0.2329	0.106*
O2	0.75910 (18)	0.32363 (11)	−0.1872 (2)	0.0596 (6)
C1	0.6450 (2)	0.02635 (17)	−0.0848 (3)	0.0472 (7)
C2	0.5756 (3)	0.03725 (19)	−0.2161 (3)	0.0553 (8)
C3	0.5169 (3)	−0.0341 (2)	−0.2832 (4)	0.0706 (9)
H3	0.4679	−0.0261	−0.3686	0.085*
C4	0.5303 (3)	−0.1141 (2)	−0.2263 (4)	0.0702 (10)
H4	0.4897	−0.1600	−0.2731	0.084*
C5	0.6039 (3)	−0.13015 (19)	−0.0983 (4)	0.0586 (8)
C6	0.6208 (3)	−0.2140 (2)	−0.0396 (4)	0.0693 (10)
H6	0.5810	−0.2604	−0.0857	0.083*
C7	0.6934 (3)	−0.2278 (2)	0.0816 (4)	0.0761 (10)
H7	0.7041	−0.2835	0.1183	0.091*
C8	0.7527 (3)	−0.1584 (2)	0.1524 (4)	0.0721 (10)
H8	0.8030	−0.1682	0.2361	0.087*
C9	0.7375 (3)	−0.07684 (18)	0.1001 (3)	0.0575 (8)
H9	0.7780	−0.0316	0.1489	0.069*
C10	0.6618 (2)	−0.05878 (17)	−0.0264 (3)	0.0480 (7)
C11	0.6973 (2)	0.10041 (17)	−0.0080 (3)	0.0494 (7)
H11	0.7299	0.0939	0.0876	0.059*
C12	0.7759 (2)	0.31563 (17)	−0.0533 (3)	0.0464 (7)
C13	0.8249 (2)	0.38767 (17)	0.0401 (3)	0.0456 (7)
C14	0.8877 (3)	0.37590 (19)	0.1745 (3)	0.0568 (8)
H14	0.9016	0.3205	0.2110	0.068*
C15	0.9292 (3)	0.4465 (2)	0.2537 (3)	0.0639 (9)
H15	0.9706	0.4374	0.3440	0.077*
C16	0.9125 (3)	0.5301 (2)	0.2056 (3)	0.0579 (8)
C17	0.8512 (3)	0.54064 (19)	0.0705 (4)	0.0626 (9)
H17	0.8382	0.5961	0.0340	0.075*
C18	0.8091 (3)	0.47147 (18)	−0.0113 (3)	0.0577 (8)
H18	0.7694	0.4809	−0.1026	0.069*
C19	0.9554 (3)	0.6073 (2)	0.2941 (4)	0.0829 (11)
H19A	1.0096	0.6410	0.2388	0.124*
H19B	0.9973	0.5883	0.3834	0.124*
H19C	0.8867	0.6419	0.3165	0.124*
H2	0.752 (3)	0.2325 (19)	0.1132 (12)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0629 (16)	0.0419 (13)	0.0516 (15)	−0.0017 (12)	0.0087 (12)	−0.0052 (12)
N2	0.0786 (18)	0.0367 (13)	0.0428 (14)	−0.0055 (12)	0.0079 (13)	−0.0006 (11)
O1	0.0734 (16)	0.0762 (15)	0.0610 (15)	0.0081 (13)	−0.0060 (12)	0.0068 (12)
O2	0.0847 (16)	0.0572 (13)	0.0364 (12)	−0.0029 (10)	−0.0010 (10)	0.0036 (9)
C1	0.0443 (17)	0.0479 (17)	0.0500 (18)	−0.0007 (13)	0.0075 (14)	−0.0086 (13)
C2	0.0518 (18)	0.0588 (19)	0.055 (2)	0.0048 (15)	0.0027 (16)	−0.0034 (16)
C3	0.052 (2)	0.094 (3)	0.065 (2)	−0.0017 (19)	−0.0027 (17)	−0.019 (2)
C4	0.058 (2)	0.069 (2)	0.084 (3)	−0.0140 (18)	0.0074 (19)	−0.029 (2)
C5	0.0523 (19)	0.057 (2)	0.067 (2)	−0.0060 (15)	0.0136 (17)	−0.0147 (17)
C6	0.074 (2)	0.049 (2)	0.087 (3)	−0.0107 (17)	0.023 (2)	−0.0150 (18)
C7	0.094 (3)	0.0457 (19)	0.091 (3)	−0.0033 (19)	0.025 (2)	0.0035 (19)
C8	0.088 (3)	0.058 (2)	0.071 (2)	0.0006 (18)	0.0055 (19)	0.0081 (17)
C9	0.070 (2)	0.0435 (17)	0.060 (2)	−0.0018 (15)	0.0105 (17)	0.0001 (15)
C10	0.0438 (17)	0.0467 (17)	0.0544 (19)	−0.0039 (13)	0.0095 (14)	−0.0081 (14)
C11	0.0538 (18)	0.0454 (17)	0.0495 (17)	0.0011 (14)	0.0065 (14)	−0.0012 (14)
C12	0.0497 (17)	0.0426 (16)	0.0471 (17)	0.0046 (13)	0.0054 (13)	0.0005 (14)
C13	0.0489 (17)	0.0470 (16)	0.0414 (16)	0.0023 (13)	0.0063 (13)	0.0020 (13)
C14	0.0601 (19)	0.0570 (19)	0.0528 (19)	−0.0048 (15)	−0.0001 (16)	0.0112 (15)
C15	0.067 (2)	0.074 (2)	0.0491 (19)	−0.0151 (18)	−0.0055 (16)	0.0005 (17)
C16	0.0520 (18)	0.063 (2)	0.059 (2)	−0.0116 (15)	0.0114 (16)	−0.0079 (16)
C17	0.074 (2)	0.0442 (17)	0.070 (2)	−0.0008 (15)	0.0066 (18)	−0.0003 (16)
C18	0.066 (2)	0.0485 (18)	0.058 (2)	−0.0002 (15)	−0.0016 (16)	0.0042 (15)
C19	0.089 (3)	0.084 (2)	0.077 (2)	−0.025 (2)	0.012 (2)	−0.024 (2)

N1—C11	1.278 (3)	C8—C9	1.358 (4)
N1—N2	1.388 (3)	C8—H8	0.9300
N2—C12	1.347 (3)	C9—C10	1.413 (4)
N2—H2	0.902 (10)	C9—H9	0.9300
O1—C2	1.344 (3)	C11—H11	0.9300
O1—H1	0.8200	C12—C13	1.486 (4)
O2—C12	1.234 (3)	C13—C14	1.386 (4)
C1—C2	1.394 (4)	C13—C18	1.388 (3)
C1—C10	1.430 (4)	C14—C15	1.375 (4)
C1—C11	1.446 (3)	C14—H14	0.9300
C2—C3	1.403 (4)	C15—C16	1.376 (4)
C3—C4	1.348 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.382 (4)
C4—C5	1.405 (4)	C16—C19	1.504 (4)
C4—H4	0.9300	C17—C18	1.371 (4)
C5—C6	1.413 (4)	C17—H17	0.9300
C5—C10	1.418 (4)	C18—H18	0.9300
C6—C7	1.344 (4)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.395 (4)	C19—H19C	0.9600
C7—H7	0.9300
C11—N1—N2	116.7 (2)	C9—C10—C1	123.0 (2)
C12—N2—N1	117.7 (2)	C5—C10—C1	120.1 (3)
C12—N2—H2	127.2 (19)	N1—C11—C1	121.3 (3)
N1—N2—H2	114.8 (19)	N1—C11—H11	119.4
C2—O1—H1	109.5	C1—C11—H11	119.4
C2—C1—C10	119.0 (3)	O2—C12—N2	121.7 (3)
C2—C1—C11	120.3 (3)	O2—C12—C13	121.5 (2)
C10—C1—C11	120.7 (3)	N2—C12—C13	116.8 (2)
O1—C2—C1	123.0 (3)	C14—C13—C18	118.0 (3)
O1—C2—C3	117.3 (3)	C14—C13—C12	123.7 (2)
C1—C2—C3	119.7 (3)	C18—C13—C12	118.3 (3)
C4—C3—C2	121.2 (3)	C15—C14—C13	119.7 (3)
C4—C3—H3	119.4	C15—C14—H14	120.2
C2—C3—H3	119.4	C13—C14—H14	120.2
C3—C4—C5	121.9 (3)	C14—C15—C16	123.1 (3)
C3—C4—H4	119.1	C14—C15—H15	118.4
C5—C4—H4	119.1	C16—C15—H15	118.4
C4—C5—C6	122.4 (3)	C15—C16—C17	116.5 (3)
C4—C5—C10	118.0 (3)	C15—C16—C19	123.0 (3)
C6—C5—C10	119.7 (3)	C17—C16—C19	120.5 (3)
C7—C6—C5	121.2 (3)	C18—C17—C16	121.8 (3)
C7—C6—H6	119.4	C18—C17—H17	119.1
C5—C6—H6	119.4	C16—C17—H17	119.1
C6—C7—C8	119.9 (3)	C17—C18—C13	121.0 (3)
C6—C7—H7	120.1	C17—C18—H18	119.5
C8—C7—H7	120.1	C13—C18—H18	119.5
C9—C8—C7	120.6 (3)	C16—C19—H19A	109.5
C9—C8—H8	119.7	C16—C19—H19B	109.5
C7—C8—H8	119.7	H19A—C19—H19B	109.5
C8—C9—C10	121.8 (3)	C16—C19—H19C	109.5
C8—C9—H9	119.1	H19A—C19—H19C	109.5
C10—C9—H9	119.1	H19B—C19—H19C	109.5
C9—C10—C5	116.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.02 (1)	2.897 (3)	164 (3)
O1—H1···N1	0.82	1.86	2.586 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.02 (1)	2.897 (3)	164 (3)
O1—H1⋯N1	0.82	1.86	2.586 (3)	146

Symmetry code: (i) .