N'-(2-Meth-oxy-1-naphthyl-idene)nicotino-hydrazide.

The title compound, C(18)H(15)N(3)O(2), was prepared by the reaction of 2-methoxy-naphthaldehyde with nicotinic acid hydrazide in methanol. The dihedral angle between the naphthalene ring system and the pyridine ring is 9.2 (3)°. An intra-molecular C-H⋯N hydrogen bond is observed. In the crystal structure, mol-ecules are linked into chains running along the c axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Sun et al. (2009 ▶); Wen et al. (2009 ▶).

Experimental

Crystal data

C18H15N3O2

M = 305.33

Tetragonal,

a = 9.6163 (13) Å

c = 17.442 (3) Å

V = 1612.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.23 × 0.21 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.981, T max = 0.983

8478 measured reflections

1498 independent reflections

1109 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.099

S = 1.03

1498 reflections

212 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536810003843/ci5027sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003843/ci5027Isup2.hkl

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

C18H15N3O2	Dx = 1.257 Mg m−3
Mr = 305.33	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 1467 reflections
Hall symbol: P 4cw	θ = 2.4–24.5°
a = 9.6163 (13) Å	µ = 0.08 mm−1
c = 17.442 (3) Å	T = 298 K
V = 1612.9 (4) Å3	Block, colourless
Z = 4	0.23 × 0.21 × 0.21 mm
F(000) = 640

Bruker APEXII CCD area-detector diffractometer	1498 independent reflections
Radiation source: fine-focus sealed tube	1109 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.981, Tmax = 0.983	k = −11→8
8478 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.054P)2 + 0.0224P] where P = (Fo2 + 2Fc2)/3
1498 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.10 e Å−3
2 restraints	Δρmin = −0.11 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 > 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	0.9936 (3)	0.0960 (3)	0.18164 (15)	0.0629 (7)
N2	1.0362 (3)	−0.0311 (3)	0.20995 (14)	0.0624 (7)
N3	1.2654 (4)	−0.3482 (3)	0.31458 (18)	0.1112 (13)
O1	0.9212 (3)	0.3474 (3)	0.35200 (18)	0.1066 (9)
O2	1.1195 (2)	−0.1023 (2)	0.09477 (13)	0.0791 (7)
C1	0.8973 (3)	0.3191 (3)	0.2190 (2)	0.0670 (9)
C2	0.8904 (4)	0.4054 (4)	0.2829 (3)	0.0843 (11)
C3	0.8547 (5)	0.5467 (5)	0.2750 (4)	0.1166 (17)
H3	0.8516	0.6039	0.3179	0.140*
C4	0.8256 (5)	0.5980 (5)	0.2064 (5)	0.1223 (19)
H4	0.8060	0.6924	0.2022	0.147*
C5	0.8231 (4)	0.5148 (4)	0.1387 (3)	0.0943 (12)
C6	0.7859 (5)	0.5685 (5)	0.0671 (4)	0.1232 (19)
H6	0.7606	0.6616	0.0632	0.148*
C7	0.7857 (5)	0.4884 (6)	0.0029 (4)	0.1166 (16)
H7	0.7618	0.5270	−0.0441	0.140*
C8	0.8218 (4)	0.3472 (5)	0.0079 (3)	0.0914 (12)
H8	0.8211	0.2915	−0.0357	0.110*
C9	0.8579 (3)	0.2925 (4)	0.0773 (2)	0.0750 (9)
H9	0.8816	0.1988	0.0799	0.090*
C10	0.8609 (3)	0.3720 (3)	0.1454 (2)	0.0691 (9)
C11	0.9425 (3)	0.1769 (3)	0.2331 (2)	0.0653 (8)
H11	0.9337	0.1422	0.2826	0.078*
C12	1.1047 (3)	−0.1204 (3)	0.16398 (18)	0.0585 (8)
C13	1.1660 (3)	−0.2433 (3)	0.20306 (16)	0.0588 (8)
C14	1.1928 (4)	−0.3620 (4)	0.1619 (2)	0.0806 (10)
H14	1.1688	−0.3673	0.1104	0.097*
C15	1.2545 (5)	−0.4718 (4)	0.1972 (2)	0.1045 (14)
H15	1.2742	−0.5528	0.1703	0.125*
C16	1.2870 (6)	−0.4605 (4)	0.2729 (3)	0.1184 (17)
H16	1.3270	−0.5371	0.2968	0.142*
C17	1.2047 (4)	−0.2419 (4)	0.2787 (2)	0.0835 (11)
H17	1.1875	−0.1616	0.3069	0.100*
C18	0.8999 (7)	0.4279 (7)	0.4200 (3)	0.161 (2)
H18A	0.9667	0.5021	0.4218	0.241*
H18B	0.9112	0.3695	0.4642	0.241*
H18C	0.8077	0.4661	0.4197	0.241*
H2	1.019 (4)	−0.056 (3)	0.2588 (9)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0601 (15)	0.0596 (15)	0.0689 (16)	0.0083 (12)	0.0102 (12)	0.0094 (13)
N2	0.0667 (17)	0.0605 (15)	0.0601 (16)	0.0105 (12)	0.0121 (13)	0.0075 (13)
N3	0.178 (3)	0.082 (2)	0.074 (2)	0.049 (2)	−0.040 (2)	−0.0153 (17)
O1	0.104 (2)	0.120 (2)	0.096 (2)	−0.0024 (16)	−0.0023 (16)	−0.038 (2)
O2	0.0954 (16)	0.0891 (16)	0.0528 (14)	0.0243 (12)	0.0153 (12)	0.0115 (11)
C1	0.0482 (17)	0.0588 (19)	0.094 (3)	−0.0012 (13)	0.0115 (16)	−0.0046 (19)
C2	0.064 (2)	0.073 (2)	0.117 (4)	−0.0071 (18)	0.009 (2)	−0.025 (3)
C3	0.113 (4)	0.073 (3)	0.163 (5)	−0.006 (2)	0.015 (4)	−0.035 (3)
C4	0.113 (4)	0.054 (2)	0.200 (6)	0.001 (2)	0.022 (4)	−0.020 (4)
C5	0.078 (2)	0.058 (2)	0.147 (4)	0.0043 (18)	0.015 (3)	0.014 (3)
C6	0.106 (3)	0.071 (3)	0.193 (6)	0.017 (2)	0.009 (4)	0.039 (4)
C7	0.096 (3)	0.110 (4)	0.143 (5)	0.011 (3)	0.002 (3)	0.049 (4)
C8	0.074 (2)	0.096 (3)	0.105 (3)	0.011 (2)	−0.001 (2)	0.021 (2)
C9	0.0583 (19)	0.073 (2)	0.094 (3)	0.0055 (16)	0.0041 (18)	0.014 (2)
C10	0.0476 (16)	0.0550 (18)	0.105 (3)	−0.0014 (14)	0.0118 (17)	0.0053 (19)
C11	0.0597 (18)	0.0667 (19)	0.070 (2)	−0.0011 (15)	0.0076 (16)	0.0000 (17)
C12	0.0563 (18)	0.0623 (19)	0.057 (2)	0.0047 (13)	0.0063 (15)	0.0040 (15)
C13	0.0664 (19)	0.0583 (18)	0.0516 (18)	0.0058 (13)	0.0016 (14)	−0.0006 (14)
C14	0.110 (3)	0.073 (2)	0.059 (2)	0.0182 (19)	0.0007 (19)	−0.0036 (18)
C15	0.164 (4)	0.075 (3)	0.075 (3)	0.039 (2)	−0.014 (3)	−0.018 (2)
C16	0.189 (5)	0.075 (3)	0.091 (3)	0.048 (3)	−0.035 (3)	−0.002 (2)
C17	0.110 (3)	0.069 (2)	0.071 (3)	0.0228 (19)	−0.022 (2)	−0.0121 (18)
C18	0.171 (5)	0.181 (5)	0.130 (5)	−0.031 (4)	−0.007 (4)	−0.088 (4)

N1—C11	1.285 (4)	C6—H6	0.93
N1—N2	1.381 (3)	C7—C8	1.404 (7)
N2—C12	1.347 (4)	C7—H7	0.93
N2—H2	0.899 (10)	C8—C9	1.365 (5)
N3—C16	1.318 (5)	C8—H8	0.93
N3—C17	1.333 (4)	C9—C10	1.413 (5)
O1—C2	1.361 (5)	C9—H9	0.93
O1—C18	1.431 (6)	C11—H11	0.93
O2—C12	1.228 (4)	C12—C13	1.486 (4)
C1—C2	1.391 (5)	C13—C17	1.371 (4)
C1—C10	1.425 (5)	C13—C14	1.373 (4)
C1—C11	1.455 (4)	C14—C15	1.358 (5)
C2—C3	1.408 (6)	C14—H14	0.93
C3—C4	1.324 (7)	C15—C16	1.361 (6)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.427 (7)	C16—H16	0.93
C4—H4	0.93	C17—H17	0.93
C5—C6	1.398 (8)	C18—H18A	0.96
C5—C10	1.425 (5)	C18—H18B	0.96
C6—C7	1.358 (7)	C18—H18C	0.96
C11—N1—N2	113.5 (3)	C10—C9—H9	118.6
C12—N2—N1	119.8 (2)	C9—C10—C1	124.7 (3)
C12—N2—H2	119 (2)	C9—C10—C5	116.5 (4)
N1—N2—H2	121 (2)	C1—C10—C5	118.8 (4)
C16—N3—C17	116.0 (3)	N1—C11—C1	124.4 (3)
C2—O1—C18	118.8 (4)	N1—C11—H11	117.8
C2—C1—C10	119.8 (3)	C1—C11—H11	117.8
C2—C1—C11	116.1 (3)	O2—C12—N2	123.5 (3)
C10—C1—C11	124.1 (3)	O2—C12—C13	121.2 (3)
O1—C2—C1	117.0 (3)	N2—C12—C13	115.3 (3)
O1—C2—C3	122.3 (5)	C17—C13—C14	117.4 (3)
C1—C2—C3	120.6 (5)	C17—C13—C12	122.8 (3)
C4—C3—C2	120.0 (5)	C14—C13—C12	119.7 (3)
C4—C3—H3	120.0	C15—C14—C13	119.4 (3)
C2—C3—H3	120.0	C15—C14—H14	120.3
C3—C4—C5	122.9 (4)	C13—C14—H14	120.3
C3—C4—H4	118.6	C14—C15—C16	118.5 (3)
C5—C4—H4	118.6	C14—C15—H15	120.7
C6—C5—C10	119.7 (5)	C16—C15—H15	120.7
C6—C5—C4	122.5 (5)	N3—C16—C15	124.3 (4)
C10—C5—C4	117.9 (5)	N3—C16—H16	117.8
C7—C6—C5	121.8 (4)	C15—C16—H16	117.8
C7—C6—H6	119.1	N3—C17—C13	124.3 (3)
C5—C6—H6	119.1	N3—C17—H17	117.9
C6—C7—C8	119.8 (5)	C13—C17—H17	117.9
C6—C7—H7	120.1	O1—C18—H18A	109.5
C8—C7—H7	120.1	O1—C18—H18B	109.5
C9—C8—C7	119.3 (5)	H18A—C18—H18B	109.5
C9—C8—H8	120.3	O1—C18—H18C	109.5
C7—C8—H8	120.3	H18A—C18—H18C	109.5
C8—C9—C10	122.8 (4)	H18B—C18—H18C	109.5
C8—C9—H9	118.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.00 (2)	2.833 (3)	154 (3)
C9—H9···N1	0.93	2.30	2.930 (5)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.00 (2)	2.833 (3)	154 (3)
C9—H9⋯N1	0.93	2.30	2.930 (5)	125

Symmetry code: (i) .