4-Meth-oxy-N'-(2-methoxy-naphthyl-idene)benzohydrazide.

The mol-ecule of the title Schiff base compound, C(20)H(18)N(2)O(3), prepared by the reaction of 2-meth-oxy-1-naphthyl-aldehyde and 4-methoxy-benzohydrazide, exists in a trans configuration with respect to the imine group. The naphthyl ring system makes a dihedral angle of 71.4 (2)° with the mean plane of the benzene ring. In the crystal structure, mol-ecules are linked into one-dimensional chains parallel to the c axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazone derivatives, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Fun et al. (2008 ▶). For our previous reports of hydrazones, see: Qiu, Fang et al. (2006 ▶); Qiu, Luo et al. (2006a ▶,b ▶); Qiu, Xu et al. (2006 ▶). For related structures, see: Singh et al. (2007 ▶); Narayana et al. (2007 ▶); Cui et al. (2007 ▶); Diao et al. (2008 ▶).

Experimental

Crystal data

C20H18N2O3

M = 334.36

Monoclinic,

a = 11.675 (3) Å

b = 17.937 (4) Å

c = 8.508 (3) Å

β = 110.288 (3)°

V = 1671.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS;Sheldrick, 1996 ▶) T min = 0.982, T max = 0.984

9333 measured reflections

3445 independent reflections

1657 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.148

S = 0.97

3445 reflections

231 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 I, global. DOI: 10.1107/S1600536808026974/bh2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026974/bh2188Isup2.hkl

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

C20H18N2O3	F000 = 704
Mr = 334.36	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1254 reflections
a = 11.675 (3) Å	θ = 2.5–24.5º
b = 17.937 (4) Å	µ = 0.09 mm−1
c = 8.508 (3) Å	T = 298 (2) K
β = 110.288 (3)º	Block, colourless
V = 1671.2 (8) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	3445 independent reflections
Radiation source: fine-focus sealed tube	1657 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
T = 298(2) K	θmax = 26.6º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS;Sheldrick, 1996)	h = −14→14
Tmin = 0.982, Tmax = 0.984	k = −22→18
9333 measured reflections	l = −10→10

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0631P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
3445 reflections	Δρmax = 0.17 e Å−3
231 parameters	Δρmin = −0.18 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.02930 (16)	0.01580 (9)	0.8049 (2)	0.0725 (6)
O2	0.25127 (15)	0.32586 (9)	0.7183 (2)	0.0629 (5)
O3	0.60192 (18)	0.45464 (11)	1.4125 (2)	0.0838 (6)
N1	0.10006 (17)	0.22371 (11)	0.7604 (3)	0.0547 (6)
N2	0.18996 (18)	0.25413 (11)	0.8945 (3)	0.0535 (6)
C1	−0.0487 (2)	0.12593 (13)	0.6609 (3)	0.0492 (6)
C2	−0.0564 (2)	0.04936 (14)	0.6724 (3)	0.0559 (7)
C3	−0.1458 (3)	0.00788 (16)	0.5506 (4)	0.0722 (8)
H3	−0.1477	−0.0438	0.5591	0.087*
C4	−0.2290 (3)	0.04341 (17)	0.4209 (4)	0.0762 (9)
H4	−0.2878	0.0154	0.3407	0.091*
C5	−0.2297 (2)	0.12115 (16)	0.4033 (3)	0.0597 (7)
C6	−0.3197 (3)	0.15768 (19)	0.2698 (4)	0.0765 (9)
H6	−0.3786	0.1295	0.1899	0.092*
C7	−0.3220 (3)	0.2322 (2)	0.2562 (4)	0.0818 (9)
H7	−0.3827	0.2553	0.1684	0.098*
C8	−0.2336 (3)	0.27484 (17)	0.3731 (4)	0.0790 (9)
H8	−0.2356	0.3265	0.3630	0.095*
C9	−0.1444 (2)	0.24203 (15)	0.5021 (4)	0.0662 (8)
H9	−0.0859	0.2718	0.5782	0.079*
C10	−0.1381 (2)	0.16348 (13)	0.5239 (3)	0.0504 (6)
C11	0.0218 (3)	−0.06329 (14)	0.8242 (4)	0.0882 (10)
H11A	−0.0584	−0.0761	0.8227	0.132*
H11B	0.0813	−0.0785	0.9290	0.132*
H11C	0.0374	−0.0883	0.7339	0.132*
C12	0.0490 (2)	0.16441 (13)	0.7918 (3)	0.0542 (7)
H12	0.0751	0.1457	0.9005	0.065*
C13	0.2622 (2)	0.30763 (13)	0.8640 (4)	0.0504 (6)
C14	0.3530 (2)	0.34273 (12)	1.0105 (3)	0.0486 (6)
C15	0.3425 (2)	0.34574 (13)	1.1687 (3)	0.0562 (7)
H15	0.2768	0.3225	1.1866	0.067*
C16	0.4276 (3)	0.38248 (15)	1.2979 (3)	0.0658 (8)
H16	0.4194	0.3830	1.4028	0.079*
C17	0.5237 (2)	0.41823 (13)	1.2766 (4)	0.0612 (8)
C18	0.5369 (2)	0.41555 (15)	1.1216 (4)	0.0670 (8)
H18	0.6028	0.4390	1.1050	0.080*
C19	0.4517 (2)	0.37779 (14)	0.9909 (3)	0.0593 (7)
H19	0.4617	0.3761	0.8872	0.071*
C20	0.6915 (3)	0.50102 (18)	1.3936 (4)	0.1010 (12)
H20A	0.7404	0.4736	1.3433	0.151*
H20B	0.7423	0.5192	1.5014	0.151*
H20C	0.6536	0.5424	1.3230	0.151*
H2	0.200 (2)	0.2348 (14)	0.9956 (19)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0747 (13)	0.0456 (11)	0.0843 (15)	−0.0046 (9)	0.0111 (11)	0.0043 (10)
O2	0.0651 (12)	0.0541 (11)	0.0604 (13)	−0.0120 (8)	0.0104 (10)	0.0021 (9)
O3	0.0788 (14)	0.0771 (13)	0.0713 (14)	−0.0238 (11)	−0.0047 (11)	−0.0070 (11)
N1	0.0450 (12)	0.0532 (13)	0.0577 (14)	−0.0072 (10)	0.0072 (11)	−0.0104 (11)
N2	0.0515 (12)	0.0488 (13)	0.0524 (14)	−0.0103 (10)	0.0083 (11)	−0.0016 (11)
C1	0.0468 (15)	0.0476 (15)	0.0547 (17)	−0.0081 (12)	0.0193 (13)	−0.0066 (13)
C2	0.0513 (16)	0.0502 (16)	0.0646 (19)	−0.0060 (13)	0.0181 (15)	−0.0040 (14)
C3	0.0683 (19)	0.0537 (17)	0.089 (2)	−0.0161 (15)	0.0197 (18)	−0.0126 (16)
C4	0.068 (2)	0.069 (2)	0.081 (2)	−0.0206 (16)	0.0136 (18)	−0.0232 (17)
C5	0.0531 (17)	0.0646 (18)	0.0578 (18)	−0.0094 (14)	0.0146 (14)	−0.0110 (15)
C6	0.0603 (19)	0.094 (3)	0.063 (2)	−0.0087 (17)	0.0059 (15)	−0.0136 (18)
C7	0.070 (2)	0.092 (3)	0.069 (2)	0.0049 (18)	0.0060 (17)	0.0046 (19)
C8	0.0643 (19)	0.0676 (19)	0.090 (2)	0.0006 (16)	0.0075 (18)	0.0054 (17)
C9	0.0542 (17)	0.0577 (18)	0.075 (2)	−0.0040 (13)	0.0078 (15)	−0.0026 (15)
C10	0.0438 (14)	0.0504 (15)	0.0572 (17)	−0.0056 (12)	0.0177 (13)	−0.0069 (13)
C11	0.103 (3)	0.0471 (18)	0.109 (3)	−0.0049 (16)	0.030 (2)	0.0073 (17)
C12	0.0488 (15)	0.0477 (15)	0.0603 (17)	−0.0032 (12)	0.0115 (13)	−0.0016 (13)
C13	0.0508 (15)	0.0391 (14)	0.0590 (18)	0.0021 (12)	0.0160 (14)	0.0056 (13)
C14	0.0418 (14)	0.0382 (13)	0.0590 (18)	−0.0006 (11)	0.0090 (13)	0.0026 (12)
C15	0.0526 (15)	0.0515 (16)	0.0634 (19)	−0.0078 (12)	0.0188 (14)	0.0006 (14)
C16	0.0723 (19)	0.0597 (17)	0.0570 (18)	−0.0077 (15)	0.0117 (16)	−0.0060 (14)
C17	0.0516 (17)	0.0424 (15)	0.073 (2)	−0.0052 (12)	0.0000 (15)	0.0074 (14)
C18	0.0535 (17)	0.0699 (19)	0.068 (2)	−0.0162 (14)	0.0087 (15)	0.0117 (16)
C19	0.0534 (16)	0.0616 (16)	0.0616 (18)	−0.0061 (13)	0.0181 (14)	0.0078 (14)
C20	0.085 (2)	0.083 (2)	0.104 (3)	−0.0336 (19)	−0.006 (2)	−0.001 (2)

O1—C2	1.361 (3)	C8—C9	1.358 (4)
O1—C11	1.434 (3)	C8—H8	0.9300
O2—C13	1.245 (3)	C9—C10	1.420 (3)
O3—C17	1.366 (3)	C9—H9	0.9300
O3—C20	1.388 (3)	C11—H11A	0.9600
N1—C12	1.292 (3)	C11—H11B	0.9600
N1—N2	1.368 (3)	C11—H11C	0.9600
N2—C13	1.361 (3)	C12—H12	0.9300
N2—H2	0.895 (10)	C13—C14	1.470 (3)
C1—C2	1.382 (3)	C14—C19	1.372 (3)
C1—C10	1.434 (3)	C14—C15	1.395 (3)
C1—C12	1.462 (3)	C15—C16	1.368 (3)
C2—C3	1.402 (4)	C15—H15	0.9300
C3—C4	1.351 (4)	C16—C17	1.358 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.402 (4)	C17—C18	1.381 (4)
C4—H4	0.9300	C18—C19	1.384 (3)
C5—C6	1.413 (4)	C18—H18	0.9300
C5—C10	1.419 (3)	C19—H19	0.9300
C6—C7	1.341 (4)	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—C8	1.388 (4)	C20—H20C	0.9600
C7—H7	0.9300
C2—O1—C11	118.4 (2)	O1—C11—H11A	109.5
C17—O3—C20	119.9 (3)	O1—C11—H11B	109.5
C12—N1—N2	115.6 (2)	H11A—C11—H11B	109.5
C13—N2—N1	118.0 (2)	O1—C11—H11C	109.5
C13—N2—H2	124.7 (18)	H11A—C11—H11C	109.5
N1—N2—H2	117.2 (18)	H11B—C11—H11C	109.5
C2—C1—C10	118.5 (2)	N1—C12—C1	121.7 (2)
C2—C1—C12	117.9 (2)	N1—C12—H12	119.2
C10—C1—C12	123.6 (2)	C1—C12—H12	119.2
O1—C2—C1	116.8 (2)	O2—C13—N2	121.3 (2)
O1—C2—C3	121.5 (2)	O2—C13—C14	121.8 (2)
C1—C2—C3	121.7 (3)	N2—C13—C14	116.9 (2)
C4—C3—C2	119.6 (3)	C19—C14—C15	117.3 (2)
C4—C3—H3	120.2	C19—C14—C13	118.9 (2)
C2—C3—H3	120.2	C15—C14—C13	123.8 (2)
C3—C4—C5	122.2 (3)	C16—C15—C14	120.7 (2)
C3—C4—H4	118.9	C16—C15—H15	119.6
C5—C4—H4	118.9	C14—C15—H15	119.6
C4—C5—C6	121.5 (3)	C17—C16—C15	121.6 (3)
C4—C5—C10	118.7 (3)	C17—C16—H16	119.2
C6—C5—C10	119.8 (3)	C15—C16—H16	119.2
C7—C6—C5	121.3 (3)	C16—C17—O3	117.0 (3)
C7—C6—H6	119.4	C16—C17—C18	118.8 (3)
C5—C6—H6	119.4	O3—C17—C18	124.1 (3)
C6—C7—C8	120.0 (3)	C17—C18—C19	119.8 (3)
C6—C7—H7	120.0	C17—C18—H18	120.1
C8—C7—H7	120.0	C19—C18—H18	120.1
C9—C8—C7	120.8 (3)	C14—C19—C18	121.7 (3)
C9—C8—H8	119.6	C14—C19—H19	119.1
C7—C8—H8	119.6	C18—C19—H19	119.1
C8—C9—C10	121.8 (3)	O3—C20—H20A	109.5
C8—C9—H9	119.1	O3—C20—H20B	109.5
C10—C9—H9	119.1	H20A—C20—H20B	109.5
C5—C10—C9	116.4 (2)	O3—C20—H20C	109.5
C5—C10—C1	119.3 (2)	H20A—C20—H20C	109.5
C9—C10—C1	124.2 (2)	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.895 (10)	2.084 (12)	2.965 (3)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.895 (10)	2.084 (12)	2.965 (3)	167 (2)

Symmetry code: (i) .