N'-[(2-Methoxynaphthalen-1-yl)methyl-idene]-4-methyl-benzohydrazide.

In the title compound, C(20)H(18)N(2)O(2), the mean planes of the naphthyl system and the benzene ring form a dihedral angle of 88.48 (10)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains, which propagate along the b-axis direction.

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For coordination compounds of benzohydrazide compounds, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010 ▶); Liu et al. (2011 ▶); Zhou et al. (2011 ▶).

Experimental

Crystal data

C20H18N2O2

M = 318.36

Orthorhombic,

a = 26.738 (3) Å

b = 4.893 (2) Å

c = 12.735 (2) Å

V = 1666.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.985

12400 measured reflections

3622 independent reflections

2579 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.03

3622 reflections

222 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.15 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/S1600536811044291/hb6475sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044291/hb6475Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044291/hb6475Isup3.cml

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

C20H18N2O2	F(000) = 672
Mr = 318.36	Dx = 1.269 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3061 reflections
a = 26.738 (3) Å	θ = 2.7–24.6°
b = 4.893 (2) Å	µ = 0.08 mm−1
c = 12.735 (2) Å	T = 298 K
V = 1666.1 (8) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker SMART 1K CCD diffractometer	3622 independent reflections
Radiation source: fine-focus sealed tube	2579 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scan	θmax = 27.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→34
Tmin = 0.984, Tmax = 0.985	k = −6→6
12400 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.1245P] where P = (Fo2 + 2Fc2)/3
3622 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.15 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	0.39864 (7)	0.4057 (4)	0.22466 (14)	0.0406 (4)
N2	0.37614 (7)	0.3174 (3)	0.31743 (15)	0.0377 (4)
O1	0.50261 (6)	−0.0340 (4)	0.11479 (13)	0.0550 (4)
O2	0.37197 (6)	0.7513 (3)	0.37919 (14)	0.0479 (4)
C1	0.44133 (8)	0.2834 (5)	0.06656 (17)	0.0389 (5)
C2	0.48465 (9)	0.1447 (5)	0.04022 (17)	0.0428 (6)
C3	0.50956 (9)	0.1928 (6)	−0.05568 (19)	0.0531 (7)
H3	0.5383	0.0953	−0.0726	0.064*
C4	0.49103 (10)	0.3836 (5)	−0.1231 (2)	0.0553 (7)
H4	0.5080	0.4173	−0.1856	0.066*
C5	0.44714 (10)	0.5312 (5)	−0.10157 (17)	0.0470 (6)
C6	0.42831 (12)	0.7288 (6)	−0.1722 (2)	0.0628 (8)
H6	0.4459	0.7662	−0.2335	0.075*
C7	0.38510 (12)	0.8652 (6)	−0.1524 (2)	0.0654 (8)
H7	0.3734	0.9951	−0.1997	0.079*
C8	0.35832 (11)	0.8088 (6)	−0.0604 (2)	0.0638 (7)
H8	0.3284	0.8996	−0.0475	0.077*
C9	0.37556 (10)	0.6224 (5)	0.01051 (19)	0.0519 (6)
H9	0.3571	0.5889	0.0710	0.062*
C10	0.42106 (9)	0.4781 (5)	−0.00566 (17)	0.0406 (5)
C11	0.54715 (10)	−0.1814 (5)	0.0936 (2)	0.0588 (7)
H11A	0.5419	−0.2991	0.0342	0.088*
H11B	0.5559	−0.2895	0.1537	0.088*
H11C	0.5737	−0.0555	0.0783	0.088*
C12	0.41801 (8)	0.2176 (5)	0.16793 (16)	0.0392 (5)
H12	0.4173	0.0374	0.1911	0.047*
C13	0.36194 (8)	0.5068 (4)	0.38880 (16)	0.0353 (5)
C14	0.33277 (8)	0.4017 (4)	0.47974 (16)	0.0339 (5)
C15	0.29756 (8)	0.1938 (5)	0.46903 (18)	0.0431 (6)
H15	0.2927	0.1121	0.4039	0.052*
C16	0.26982 (9)	0.1080 (5)	0.5540 (2)	0.0520 (7)
H16	0.2461	−0.0289	0.5448	0.062*
C17	0.27637 (10)	0.2201 (5)	0.6521 (2)	0.0533 (6)
C18	0.31194 (10)	0.4258 (5)	0.6632 (2)	0.0564 (7)
H18	0.3174	0.5029	0.7289	0.068*
C19	0.33931 (9)	0.5176 (5)	0.57820 (17)	0.0471 (6)
H19	0.3623	0.6583	0.5871	0.056*
C20	0.24619 (14)	0.1207 (8)	0.7453 (3)	0.0932 (12)
H20A	0.2142	0.2093	0.7456	0.140*
H20B	0.2637	0.1632	0.8090	0.140*
H20C	0.2416	−0.0735	0.7402	0.140*
H2	0.3739 (14)	0.134 (2)	0.327 (4)	0.140*

	U11	U22	U33	U12	U13	U23
N1	0.0471 (11)	0.0428 (11)	0.0319 (9)	−0.0044 (9)	0.0060 (9)	0.0064 (9)
N2	0.0451 (10)	0.0348 (10)	0.0333 (9)	−0.0005 (8)	0.0086 (8)	0.0070 (8)
O1	0.0488 (9)	0.0704 (11)	0.0460 (9)	0.0119 (8)	0.0065 (8)	0.0002 (9)
O2	0.0555 (10)	0.0324 (8)	0.0556 (10)	−0.0001 (7)	0.0122 (8)	0.0062 (8)
C1	0.0402 (13)	0.0453 (13)	0.0312 (11)	−0.0080 (11)	0.0031 (9)	−0.0036 (10)
C2	0.0435 (14)	0.0476 (14)	0.0373 (12)	−0.0080 (11)	0.0031 (11)	−0.0055 (11)
C3	0.0465 (14)	0.0647 (18)	0.0481 (15)	−0.0092 (12)	0.0131 (12)	−0.0086 (13)
C4	0.0606 (16)	0.0677 (16)	0.0376 (13)	−0.0278 (14)	0.0113 (13)	−0.0028 (14)
C5	0.0592 (16)	0.0480 (13)	0.0337 (12)	−0.0210 (12)	0.0000 (11)	0.0012 (11)
C6	0.082 (2)	0.0661 (18)	0.0405 (14)	−0.0274 (16)	−0.0026 (14)	0.0111 (14)
C7	0.088 (2)	0.0613 (17)	0.0475 (16)	−0.0176 (17)	−0.0151 (15)	0.0187 (14)
C8	0.0687 (18)	0.0642 (18)	0.0584 (17)	−0.0008 (15)	−0.0142 (15)	0.0072 (15)
C9	0.0550 (16)	0.0598 (16)	0.0409 (14)	−0.0032 (14)	−0.0017 (12)	0.0055 (13)
C10	0.0451 (13)	0.0432 (12)	0.0336 (11)	−0.0168 (11)	−0.0001 (10)	−0.0029 (11)
C11	0.0518 (15)	0.0591 (16)	0.0654 (17)	0.0086 (13)	0.0039 (13)	−0.0109 (14)
C12	0.0420 (12)	0.0425 (13)	0.0332 (11)	−0.0010 (10)	0.0029 (10)	0.0005 (11)
C13	0.0348 (11)	0.0361 (12)	0.0350 (12)	0.0067 (9)	−0.0028 (9)	0.0036 (10)
C14	0.0326 (11)	0.0335 (11)	0.0356 (11)	0.0062 (9)	0.0014 (9)	0.0009 (10)
C15	0.0413 (13)	0.0464 (14)	0.0415 (13)	0.0017 (11)	0.0048 (11)	0.0014 (11)
C16	0.0427 (15)	0.0519 (15)	0.0614 (18)	−0.0043 (12)	0.0133 (12)	0.0033 (14)
C17	0.0524 (15)	0.0604 (16)	0.0470 (15)	0.0088 (13)	0.0162 (12)	0.0103 (13)
C18	0.0699 (17)	0.0652 (17)	0.0341 (12)	0.0074 (14)	0.0070 (13)	−0.0037 (12)
C19	0.0527 (15)	0.0457 (13)	0.0428 (13)	−0.0022 (11)	0.0001 (12)	−0.0030 (12)
C20	0.100 (3)	0.114 (3)	0.066 (2)	0.006 (2)	0.0454 (18)	0.0203 (19)

N1—C12	1.280 (3)	C8—H8	0.9300
N1—N2	1.394 (2)	C9—C10	1.422 (3)
N2—C13	1.352 (3)	C9—H9	0.9300
N2—H2	0.907 (10)	C11—H11A	0.9600
O1—C2	1.378 (3)	C11—H11B	0.9600
O1—C11	1.418 (3)	C11—H11C	0.9600
O2—C13	1.232 (2)	C12—H12	0.9300
C1—C2	1.384 (3)	C13—C14	1.488 (3)
C1—C10	1.431 (3)	C14—C19	1.387 (3)
C1—C12	1.469 (3)	C14—C15	1.393 (3)
C2—C3	1.411 (3)	C15—C16	1.378 (3)
C3—C4	1.362 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.376 (4)
C4—C5	1.405 (4)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.392 (4)
C5—C6	1.413 (4)	C17—C20	1.515 (4)
C5—C10	1.430 (3)	C18—C19	1.381 (3)
C6—C7	1.358 (4)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.401 (4)	C20—H20A	0.9600
C7—H7	0.9300	C20—H20B	0.9600
C8—C9	1.364 (3)	C20—H20C	0.9600
C12—N1—N2	115.47 (17)	O1—C11—H11B	109.5
C13—N2—N1	118.57 (17)	H11A—C11—H11B	109.5
C13—N2—H2	124 (3)	O1—C11—H11C	109.5
N1—N2—H2	117 (3)	H11A—C11—H11C	109.5
C2—O1—C11	119.0 (2)	H11B—C11—H11C	109.5
C2—C1—C10	119.2 (2)	N1—C12—C1	120.7 (2)
C2—C1—C12	117.4 (2)	N1—C12—H12	119.7
C10—C1—C12	123.4 (2)	C1—C12—H12	119.7
O1—C2—C1	115.8 (2)	O2—C13—N2	122.5 (2)
O1—C2—C3	122.5 (2)	O2—C13—C14	121.80 (19)
C1—C2—C3	121.6 (2)	N2—C13—C14	115.69 (18)
C4—C3—C2	119.2 (2)	C19—C14—C15	118.19 (19)
C4—C3—H3	120.4	C19—C14—C13	119.75 (19)
C2—C3—H3	120.4	C15—C14—C13	122.04 (19)
C3—C4—C5	122.2 (2)	C16—C15—C14	120.6 (2)
C3—C4—H4	118.9	C16—C15—H15	119.7
C5—C4—H4	118.9	C14—C15—H15	119.7
C4—C5—C6	121.7 (2)	C17—C16—C15	121.6 (2)
C4—C5—C10	118.7 (2)	C17—C16—H16	119.2
C6—C5—C10	119.6 (2)	C15—C16—H16	119.2
C7—C6—C5	121.4 (3)	C16—C17—C18	117.8 (2)
C7—C6—H6	119.3	C16—C17—C20	121.0 (3)
C5—C6—H6	119.3	C18—C17—C20	121.1 (3)
C6—C7—C8	119.5 (3)	C19—C18—C17	121.2 (2)
C6—C7—H7	120.2	C19—C18—H18	119.4
C8—C7—H7	120.2	C17—C18—H18	119.4
C9—C8—C7	120.9 (3)	C18—C19—C14	120.6 (2)
C9—C8—H8	119.6	C18—C19—H19	119.7
C7—C8—H8	119.6	C14—C19—H19	119.7
C8—C9—C10	121.7 (2)	C17—C20—H20A	109.5
C8—C9—H9	119.2	C17—C20—H20B	109.5
C10—C9—H9	119.2	H20A—C20—H20B	109.5
C9—C10—C5	116.8 (2)	C17—C20—H20C	109.5
C9—C10—C1	124.2 (2)	H20A—C20—H20C	109.5
C5—C10—C1	119.0 (2)	H20B—C20—H20C	109.5
O1—C11—H11A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.91 (1)	1.99 (1)	2.882 (2)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.91 (1)	1.99 (1)	2.882 (2)	168 (4)

Symmetry code: (i) .