1-[(E)-(3,4-Dimethyl-isoxazol-5-yl)imino-meth-yl]-2-naphthol.

The title Schiff base compound, C(16)H(14)N(2)O(2), has been synthesized by the reaction of 5-amino-3,4-dimethyl-isoxazole and 2-hydr-oxy-1-naphthaldehyde. The dihedral angle between the isoxazole ring and the napthyl ring system is 3.29 (7)°. The mol-ecule adopts an E configuration about the central C=N double bond. Intra-molecular O-H⋯N hydrogen bonding generates an S(6) ring motif. In the crystal structure, π-π inter-actions are observed involving the isoxazole ring and the substituted benzene ring of the naphthyl unit, with centroid-centroid distances of 3.5200 (10) Å.

Related literature

For related background and the biological activity of isoxazol, see: Howell & Kimmel (2008 ▶); Bartlett & Schleyerbach (1985 ▶); Lamani et al. (2009 ▶); Jayashankar et al. (2009 ▶). For related structures, see: Alvarez-Thon et al. (2006 ▶); Tahir et al. (2008 ▶); Shad et al. (2008 ▶); Fun et al. (2010 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Monoclinic,

a = 7.5250 (6) Å

b = 15.4643 (12) Å

c = 12.3982 (7) Å

β = 117.377 (4)°

V = 1281.17 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.79 × 0.06 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.996

16577 measured reflections

3704 independent reflections

2843 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.05

3704 reflections

237 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001216X/sj2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001216X/sj2761Isup2.hkl

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

C16H14N2O2	F(000) = 560
Mr = 266.29	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3616 reflections
a = 7.5250 (6) Å	θ = 2.6–34.2°
b = 15.4643 (12) Å	µ = 0.09 mm−1
c = 12.3982 (7) Å	T = 100 K
β = 117.377 (4)°	Needle, yellow
V = 1281.17 (16) Å3	0.79 × 0.06 × 0.05 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	3704 independent reflections
Radiation source: fine-focus sealed tube	2843 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.930, Tmax = 0.996	k = −21→21
16577 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.3682P] where P = (Fo2 + 2Fc2)/3
3704 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.20289 (17)	1.11942 (6)	0.64493 (8)	0.0209 (2)
O2	0.24094 (15)	0.97368 (6)	0.30327 (8)	0.0173 (2)
N1	0.24292 (17)	1.04190 (6)	0.47613 (9)	0.0152 (2)
N2	0.21030 (18)	0.99921 (7)	0.18571 (9)	0.0182 (2)
C1	0.2410 (2)	1.04273 (7)	0.70239 (11)	0.0150 (2)
C2	0.2479 (2)	1.04255 (8)	0.81837 (11)	0.0179 (3)
C3	0.2877 (2)	0.96778 (8)	0.88407 (11)	0.0172 (3)
C4	0.3177 (2)	0.88841 (8)	0.83642 (11)	0.0149 (2)
C5	0.3597 (2)	0.81113 (8)	0.90574 (12)	0.0184 (3)
C6	0.3833 (2)	0.73399 (8)	0.85954 (12)	0.0201 (3)
C7	0.3626 (2)	0.73093 (8)	0.74058 (12)	0.0207 (3)
C8	0.3253 (2)	0.80526 (8)	0.67215 (12)	0.0177 (3)
C9	0.30404 (19)	0.88660 (7)	0.71809 (11)	0.0141 (2)
C10	0.26908 (19)	0.96648 (7)	0.65075 (11)	0.0138 (2)
C11	0.2611 (2)	0.96861 (8)	0.53223 (11)	0.0148 (2)
C12	0.2289 (2)	1.04637 (7)	0.36180 (11)	0.0146 (2)
C13	0.1957 (2)	1.11763 (7)	0.29069 (11)	0.0140 (2)
C14	0.18303 (19)	1.08332 (8)	0.18048 (11)	0.0151 (2)
C15	0.1393 (2)	1.13268 (9)	0.06759 (12)	0.0201 (3)
C16	0.1737 (2)	1.20938 (8)	0.31960 (12)	0.0175 (3)
H2A	0.222 (3)	1.0979 (12)	0.8512 (16)	0.029 (5)*
H3A	0.290 (3)	0.9681 (11)	0.9648 (16)	0.024 (4)*
H5A	0.375 (3)	0.8132 (11)	0.9894 (16)	0.027 (4)*
H6A	0.416 (3)	0.6822 (12)	0.9078 (16)	0.027 (4)*
H7A	0.376 (3)	0.6775 (12)	0.7059 (16)	0.029 (5)*
H8A	0.309 (3)	0.8009 (11)	0.5908 (15)	0.022 (4)*
H11A	0.272 (3)	0.9140 (11)	0.4942 (15)	0.026 (4)*
H15A	0.091 (3)	1.0970 (12)	0.0011 (17)	0.032 (5)*
H15B	0.256 (3)	1.1642 (14)	0.0772 (18)	0.043 (6)*
H15C	0.034 (3)	1.1763 (14)	0.0517 (18)	0.043 (6)*
H16A	0.202 (3)	1.2197 (12)	0.4021 (18)	0.036 (5)*
H16B	0.263 (4)	1.2459 (16)	0.302 (2)	0.053 (6)*
H16C	0.041 (4)	1.2329 (14)	0.266 (2)	0.047 (6)*
H1O1	0.207 (4)	1.1091 (15)	0.569 (2)	0.055 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0339 (6)	0.0115 (4)	0.0197 (4)	0.0004 (4)	0.0144 (4)	0.0013 (3)
O2	0.0244 (5)	0.0130 (4)	0.0163 (4)	0.0015 (4)	0.0109 (4)	0.0002 (3)
N1	0.0175 (5)	0.0146 (5)	0.0133 (5)	0.0000 (4)	0.0069 (4)	0.0012 (3)
N2	0.0232 (6)	0.0186 (5)	0.0150 (5)	0.0001 (4)	0.0107 (5)	0.0001 (4)
C1	0.0173 (6)	0.0123 (5)	0.0150 (5)	−0.0015 (4)	0.0070 (5)	0.0004 (4)
C2	0.0223 (7)	0.0155 (5)	0.0166 (5)	−0.0020 (5)	0.0095 (5)	−0.0032 (4)
C3	0.0189 (6)	0.0188 (6)	0.0143 (5)	−0.0033 (5)	0.0080 (5)	−0.0013 (4)
C4	0.0135 (6)	0.0160 (5)	0.0149 (5)	−0.0009 (4)	0.0061 (5)	0.0014 (4)
C5	0.0183 (6)	0.0204 (6)	0.0170 (5)	−0.0006 (5)	0.0085 (5)	0.0046 (4)
C6	0.0193 (6)	0.0171 (6)	0.0246 (6)	0.0001 (5)	0.0106 (5)	0.0063 (5)
C7	0.0240 (7)	0.0147 (6)	0.0261 (6)	0.0033 (5)	0.0139 (6)	0.0029 (5)
C8	0.0218 (7)	0.0146 (5)	0.0199 (6)	0.0017 (5)	0.0123 (5)	0.0007 (4)
C9	0.0141 (6)	0.0137 (5)	0.0150 (5)	0.0004 (4)	0.0072 (5)	0.0013 (4)
C10	0.0148 (6)	0.0125 (5)	0.0144 (5)	0.0000 (4)	0.0068 (5)	0.0003 (4)
C11	0.0151 (6)	0.0139 (5)	0.0153 (5)	0.0004 (5)	0.0069 (5)	0.0004 (4)
C12	0.0158 (6)	0.0141 (5)	0.0132 (5)	−0.0011 (5)	0.0062 (5)	−0.0014 (4)
C13	0.0147 (6)	0.0136 (5)	0.0139 (5)	−0.0009 (4)	0.0066 (5)	−0.0003 (4)
C14	0.0142 (6)	0.0166 (5)	0.0152 (5)	−0.0005 (5)	0.0073 (5)	0.0001 (4)
C15	0.0244 (7)	0.0220 (6)	0.0153 (6)	−0.0011 (6)	0.0105 (5)	0.0017 (5)
C16	0.0216 (7)	0.0130 (5)	0.0175 (6)	0.0006 (5)	0.0085 (5)	0.0001 (4)

O1—C1	1.3448 (14)	C6—H6A	0.962 (18)
O1—H1O1	0.97 (2)	C7—C8	1.3787 (17)
O2—C12	1.3635 (14)	C7—H7A	0.957 (19)
O2—N2	1.4229 (13)	C8—C9	1.4198 (16)
N1—C11	1.3036 (15)	C8—H8A	0.962 (17)
N1—C12	1.3739 (15)	C9—C10	1.4457 (16)
N2—C14	1.3138 (16)	C10—C11	1.4431 (16)
C1—C10	1.4033 (16)	C11—H11A	0.989 (18)
C1—C2	1.4147 (17)	C12—C13	1.3607 (16)
C2—C3	1.3659 (17)	C13—C14	1.4274 (16)
C2—H2A	1.004 (19)	C13—C16	1.4912 (16)
C3—C4	1.4245 (17)	C14—C15	1.4920 (17)
C3—H3A	0.991 (18)	C15—H15A	0.916 (19)
C4—C5	1.4203 (17)	C15—H15B	0.96 (2)
C4—C9	1.4231 (16)	C15—H15C	0.99 (2)
C5—C6	1.3696 (19)	C16—H16A	0.96 (2)
C5—H5A	0.990 (18)	C16—H16B	0.98 (3)
C6—C7	1.4108 (19)	C16—H16C	0.98 (2)
C1—O1—H1O1	105.9 (14)	C8—C9—C10	123.34 (11)
C12—O2—N2	107.29 (9)	C4—C9—C10	119.09 (11)
C11—N1—C12	122.26 (10)	C1—C10—C11	120.06 (10)
C14—N2—O2	105.86 (9)	C1—C10—C9	118.69 (11)
O1—C1—C10	122.65 (11)	C11—C10—C9	121.25 (10)
O1—C1—C2	116.06 (10)	N1—C11—C10	120.54 (11)
C10—C1—C2	121.28 (11)	N1—C11—H11A	120.0 (10)
C3—C2—C1	120.22 (11)	C10—C11—H11A	119.5 (10)
C3—C2—H2A	120.6 (10)	C13—C12—O2	111.11 (10)
C1—C2—H2A	119.2 (10)	C13—C12—N1	127.84 (11)
C2—C3—C4	121.00 (11)	O2—C12—N1	121.01 (10)
C2—C3—H3A	119.7 (10)	C12—C13—C14	103.35 (10)
C4—C3—H3A	119.3 (10)	C12—C13—C16	128.48 (11)
C5—C4—C9	119.85 (11)	C14—C13—C16	128.16 (11)
C5—C4—C3	120.52 (11)	N2—C14—C13	112.37 (11)
C9—C4—C3	119.63 (11)	N2—C14—C15	120.98 (11)
C6—C5—C4	121.03 (12)	C13—C14—C15	126.63 (11)
C6—C5—H5A	119.4 (10)	C14—C15—H15A	111.2 (12)
C4—C5—H5A	119.5 (10)	C14—C15—H15B	110.3 (12)
C5—C6—C7	119.55 (12)	H15A—C15—H15B	112.1 (18)
C5—C6—H6A	120.8 (11)	C14—C15—H15C	110.3 (12)
C7—C6—H6A	119.7 (11)	H15A—C15—H15C	106.4 (16)
C8—C7—C6	120.58 (12)	H15B—C15—H15C	106.3 (18)
C8—C7—H7A	118.5 (11)	C13—C16—H16A	114.9 (11)
C6—C7—H7A	120.9 (11)	C13—C16—H16B	109.5 (14)
C7—C8—C9	121.36 (12)	H16A—C16—H16B	107.7 (18)
C7—C8—H8A	118.6 (10)	C13—C16—H16C	112.3 (13)
C9—C8—H8A	120.0 (10)	H16A—C16—H16C	108.8 (19)
C8—C9—C4	117.57 (11)	H16B—C16—H16C	102.8 (19)
C12—O2—N2—C14	0.20 (14)	C8—C9—C10—C1	177.05 (13)
O1—C1—C2—C3	−179.34 (12)	C4—C9—C10—C1	−2.75 (19)
C10—C1—C2—C3	1.7 (2)	C8—C9—C10—C11	−2.4 (2)
C1—C2—C3—C4	−1.7 (2)	C4—C9—C10—C11	177.78 (12)
C2—C3—C4—C5	179.74 (13)	C12—N1—C11—C10	−178.04 (12)
C2—C3—C4—C9	−0.7 (2)	C1—C10—C11—N1	5.2 (2)
C9—C4—C5—C6	−1.5 (2)	C9—C10—C11—N1	−175.36 (12)
C3—C4—C5—C6	178.15 (13)	N2—O2—C12—C13	−1.01 (15)
C4—C5—C6—C7	−0.9 (2)	N2—O2—C12—N1	176.88 (12)
C5—C6—C7—C8	2.1 (2)	C11—N1—C12—C13	175.02 (14)
C6—C7—C8—C9	−0.8 (2)	C11—N1—C12—O2	−2.5 (2)
C7—C8—C9—C4	−1.5 (2)	O2—C12—C13—C14	1.33 (15)
C7—C8—C9—C10	178.66 (13)	N1—C12—C13—C14	−176.38 (13)
C5—C4—C9—C8	2.64 (19)	O2—C12—C13—C16	−179.77 (13)
C3—C4—C9—C8	−176.96 (12)	N1—C12—C13—C16	2.5 (2)
C5—C4—C9—C10	−177.54 (12)	O2—N2—C14—C13	0.64 (15)
C3—C4—C9—C10	2.85 (19)	O2—N2—C14—C15	−177.96 (12)
O1—C1—C10—C11	1.1 (2)	C12—C13—C14—N2	−1.23 (16)
C2—C1—C10—C11	179.96 (13)	C16—C13—C14—N2	179.86 (13)
O1—C1—C10—C9	−178.36 (12)	C12—C13—C14—C15	177.28 (13)
C2—C1—C10—C9	0.5 (2)	C16—C13—C14—C15	−1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.97 (2)	1.66 (3)	2.5471 (15)	150 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.97 (2)	1.66 (3)	2.5471 (15)	150 (2)