N'-(2-Hydroxy-naphthyl-idene)-4-methoxy-benzo-hydrazide.

The title Schiff base compound, C(19)H(16)N(2)O(3), was derived from the condensation reaction of 2-hydr-oxy-1-naphthyl-aldehyde with 4-methoxy-benzohydrazide. The dihedral angle between the benzene ring and the naphthyl ring system is 6.8 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O inter-molecular hydrogen bonds, forming chains running along the c axis.

Related literature

For related structures, see: Tang (2006 ▶, 2007a ▶,b ▶,c ▶,d ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H16N2O3

M = 320.34

Monoclinic,

a = 11.159 (2) Å

b = 15.790 (3) Å

c = 8.8300 (18) Å

β = 91.70 (3)°

V = 1555.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.32 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.972

13232 measured reflections

3550 independent reflections

2161 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.136

S = 1.04

3550 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 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/S1600536808008076/sj2478sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008076/sj2478Isup2.hkl

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

C19H16N2O3	F000 = 672
Mr = 320.34	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1378 reflections
a = 11.159 (2) Å	θ = 2.2–24.5º
b = 15.790 (3) Å	µ = 0.09 mm−1
c = 8.8300 (18) Å	T = 298 (2) K
β = 91.70 (3)º	Cut from a needle, colorless
V = 1555.2 (5) Å3	0.32 × 0.32 × 0.30 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3550 independent reflections
Radiation source: fine-focus sealed tube	2161 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.052
T = 298(2) K	θmax = 27.5º
ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.971, Tmax = 0.972	k = −20→20
13232 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.168P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3550 reflections	Δρmax = 0.18 e Å−3
222 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	0.44682 (14)	0.12307 (9)	0.77419 (16)	0.0569 (4)
H1	0.4089	0.1584	0.7244	0.085*
O2	0.24817 (13)	0.32717 (8)	0.67361 (14)	0.0515 (4)
O3	0.02184 (13)	0.57256 (9)	0.17402 (17)	0.0602 (5)
N1	0.30518 (14)	0.17750 (9)	0.55897 (17)	0.0415 (4)
N2	0.25139 (15)	0.24056 (10)	0.47098 (17)	0.0423 (4)
C1	0.35505 (16)	0.03145 (12)	0.5862 (2)	0.0362 (4)
C2	0.42732 (17)	0.04559 (13)	0.7145 (2)	0.0431 (5)
C3	0.48691 (18)	−0.02246 (15)	0.7874 (2)	0.0520 (6)
H3	0.5370	−0.0121	0.8715	0.062*
C4	0.47221 (19)	−0.10234 (14)	0.7367 (2)	0.0526 (6)
H4	0.5124	−0.1462	0.7868	0.063*
C5	0.39740 (17)	−0.12109 (13)	0.6096 (2)	0.0434 (5)
C6	0.3824 (2)	−0.20495 (13)	0.5558 (3)	0.0561 (6)
H6	0.4230	−0.2489	0.6051	0.067*
C7	0.3101 (2)	−0.22238 (14)	0.4342 (3)	0.0608 (6)
H7	0.3007	−0.2779	0.4007	0.073*
C8	0.2498 (2)	−0.15638 (14)	0.3591 (3)	0.0586 (6)
H8	0.2005	−0.1683	0.2750	0.070*
C9	0.26197 (18)	−0.07449 (12)	0.4075 (2)	0.0458 (5)
H9	0.2198	−0.0318	0.3566	0.055*
C10	0.33734 (16)	−0.05348 (11)	0.5331 (2)	0.0371 (5)
C11	0.29956 (17)	0.10221 (12)	0.5053 (2)	0.0388 (5)
H11	0.2594	0.0926	0.4131	0.047*
C12	0.22727 (17)	0.31534 (11)	0.5375 (2)	0.0376 (5)
C13	0.17287 (17)	0.38188 (11)	0.4404 (2)	0.0365 (4)
C14	0.18459 (18)	0.46552 (12)	0.4857 (2)	0.0454 (5)
H14	0.2259	0.4778	0.5761	0.054*
C15	0.13651 (19)	0.53130 (12)	0.4000 (2)	0.0493 (5)
H15	0.1466	0.5871	0.4317	0.059*
C16	0.07353 (17)	0.51333 (12)	0.2674 (2)	0.0427 (5)
C17	0.05869 (18)	0.43022 (12)	0.2214 (2)	0.0453 (5)
H17	0.0147	0.4180	0.1329	0.054*
C18	0.10864 (17)	0.36569 (12)	0.3058 (2)	0.0406 (5)
H18	0.0995	0.3101	0.2725	0.049*
C19	0.0515 (2)	0.65852 (13)	0.2009 (3)	0.0685 (7)
H19A	0.0224	0.6755	0.2974	0.103*
H19B	0.0153	0.6931	0.1227	0.103*
H19C	0.1370	0.6652	0.2007	0.103*
H2	0.251 (2)	0.2301 (14)	0.3703 (12)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0614 (11)	0.0580 (10)	0.0505 (10)	−0.0051 (8)	−0.0100 (8)	−0.0063 (8)
O2	0.0791 (11)	0.0422 (8)	0.0326 (8)	0.0005 (7)	−0.0063 (7)	−0.0019 (6)
O3	0.0683 (11)	0.0440 (9)	0.0674 (11)	0.0126 (7)	−0.0113 (8)	0.0084 (8)
N1	0.0508 (11)	0.0356 (9)	0.0380 (9)	0.0008 (8)	0.0009 (8)	0.0047 (7)
N2	0.0608 (11)	0.0320 (9)	0.0339 (9)	0.0046 (8)	−0.0029 (9)	0.0013 (7)
C1	0.0350 (10)	0.0388 (11)	0.0350 (11)	0.0019 (8)	0.0038 (8)	0.0062 (8)
C2	0.0391 (11)	0.0500 (13)	0.0405 (12)	−0.0026 (10)	0.0036 (9)	0.0034 (10)
C3	0.0414 (12)	0.0728 (16)	0.0413 (13)	0.0038 (11)	−0.0065 (10)	0.0114 (11)
C4	0.0465 (13)	0.0549 (14)	0.0564 (14)	0.0122 (10)	0.0035 (11)	0.0204 (11)
C5	0.0371 (11)	0.0461 (12)	0.0474 (12)	0.0058 (9)	0.0077 (9)	0.0119 (10)
C6	0.0589 (15)	0.0399 (13)	0.0700 (16)	0.0138 (11)	0.0121 (12)	0.0144 (11)
C7	0.0684 (16)	0.0394 (13)	0.0750 (17)	0.0035 (11)	0.0085 (14)	−0.0022 (12)
C8	0.0658 (16)	0.0512 (14)	0.0586 (15)	−0.0033 (11)	−0.0020 (12)	−0.0065 (11)
C9	0.0500 (13)	0.0380 (11)	0.0492 (13)	0.0013 (9)	−0.0004 (10)	0.0014 (9)
C10	0.0349 (11)	0.0396 (11)	0.0370 (11)	0.0022 (9)	0.0062 (9)	0.0069 (9)
C11	0.0421 (12)	0.0395 (11)	0.0348 (11)	−0.0008 (9)	0.0006 (9)	0.0035 (9)
C12	0.0423 (11)	0.0359 (11)	0.0346 (11)	−0.0056 (8)	0.0005 (9)	−0.0003 (8)
C13	0.0397 (11)	0.0349 (10)	0.0350 (11)	−0.0017 (8)	0.0033 (8)	−0.0002 (8)
C14	0.0545 (13)	0.0409 (12)	0.0403 (12)	−0.0017 (10)	−0.0045 (10)	−0.0061 (9)
C15	0.0609 (14)	0.0322 (11)	0.0547 (14)	0.0017 (10)	−0.0011 (11)	−0.0036 (10)
C16	0.0408 (11)	0.0412 (12)	0.0458 (12)	0.0050 (9)	−0.0008 (9)	0.0032 (9)
C17	0.0454 (13)	0.0479 (13)	0.0421 (12)	−0.0002 (10)	−0.0077 (10)	−0.0004 (10)
C18	0.0467 (12)	0.0351 (11)	0.0397 (11)	−0.0029 (9)	−0.0020 (9)	−0.0046 (9)
C19	0.0857 (19)	0.0414 (13)	0.0784 (18)	0.0172 (12)	0.0019 (14)	0.0076 (12)

O1—C2	1.347 (2)	C7—C8	1.397 (3)
O1—H1	0.8200	C7—H7	0.9300
O2—C12	1.231 (2)	C8—C9	1.367 (3)
O3—C16	1.363 (2)	C8—H8	0.9300
O3—C19	1.415 (2)	C9—C10	1.411 (3)
N1—C11	1.281 (2)	C9—H9	0.9300
N1—N2	1.388 (2)	C11—H11	0.9300
N2—C12	1.350 (2)	C12—C13	1.475 (3)
N2—H2	0.904 (9)	C13—C14	1.385 (2)
C1—C2	1.389 (3)	C13—C18	1.394 (3)
C1—C10	1.432 (2)	C14—C15	1.384 (3)
C1—C11	1.455 (2)	C14—H14	0.9300
C2—C3	1.409 (3)	C15—C16	1.377 (3)
C3—C4	1.347 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.382 (3)
C4—C5	1.410 (3)	C17—C18	1.371 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.415 (3)	C18—H18	0.9300
C5—C10	1.421 (3)	C19—H19A	0.9600
C6—C7	1.352 (3)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C2—O1—H1	109.5	C9—C10—C5	117.31 (18)
C16—O3—C19	117.63 (17)	C9—C10—C1	123.40 (17)
C11—N1—N2	116.28 (16)	C5—C10—C1	119.29 (18)
C12—N2—N1	118.18 (15)	N1—C11—C1	121.04 (18)
C12—N2—H2	126.4 (15)	N1—C11—H11	119.5
N1—N2—H2	114.0 (15)	C1—C11—H11	119.5
C2—C1—C10	119.24 (17)	O2—C12—N2	121.54 (17)
C2—C1—C11	120.36 (18)	O2—C12—C13	121.46 (17)
C10—C1—C11	120.39 (17)	N2—C12—C13	116.99 (16)
O1—C2—C1	123.23 (18)	C14—C13—C18	117.57 (18)
O1—C2—C3	116.45 (18)	C14—C13—C12	118.53 (17)
C1—C2—C3	120.31 (19)	C18—C13—C12	123.89 (17)
C4—C3—C2	120.7 (2)	C15—C14—C13	121.75 (19)
C4—C3—H3	119.6	C15—C14—H14	119.1
C2—C3—H3	119.6	C13—C14—H14	119.1
C3—C4—C5	121.63 (19)	C16—C15—C14	119.34 (19)
C3—C4—H4	119.2	C16—C15—H15	120.3
C5—C4—H4	119.2	C14—C15—H15	120.3
C4—C5—C6	121.66 (19)	O3—C16—C15	124.67 (18)
C4—C5—C10	118.73 (19)	O3—C16—C17	115.39 (18)
C6—C5—C10	119.6 (2)	C15—C16—C17	119.94 (18)
C7—C6—C5	121.3 (2)	C18—C17—C16	120.17 (18)
C7—C6—H6	119.4	C18—C17—H17	119.9
C5—C6—H6	119.4	C16—C17—H17	119.9
C6—C7—C8	119.5 (2)	C17—C18—C13	121.20 (18)
C6—C7—H7	120.2	C17—C18—H18	119.4
C8—C7—H7	120.2	C13—C18—H18	119.4
C9—C8—C7	121.0 (2)	O3—C19—H19A	109.5
C9—C8—H8	119.5	O3—C19—H19B	109.5
C7—C8—H8	119.5	H19A—C19—H19B	109.5
C8—C9—C10	121.29 (19)	O3—C19—H19C	109.5
C8—C9—H9	119.4	H19A—C19—H19C	109.5
C10—C9—H9	119.4	H19B—C19—H19C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.582 (2)	146
N2—H2···O2i	0.904 (9)	1.957 (12)	2.834 (2)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.582 (2)	146
N2—H2⋯O2i	0.904 (9)	1.957 (12)	2.834 (2)	163 (2)

Symmetry code: (i) .