1-[(E)-(2-Phenoxy-anilino)methyl-ene]naphthalen-2(1H)-one.

The mol-ecule of the title compound, C(23)H(17)NO(2), a Schiff base derived from 2-hydr-oxy-1-naphthaldehyde, crystallizes in the keto-amine tautomeric form. The dihedral angle between the aniline and hydroxy-benzene rings is 77.41 (17)°, whereas the planes of the naphthaldehyde and fused aniline benzene rings are nearly coplanar, making a dihedral angle of 8.29 (15)°. Intra-molecular N-H⋯O hydrogen bonding, a characteristic hydrogen bond for Schiff bases, helps to stabilize the mol-ecular structure. Weak inter-molecular C-H⋯π inter-actions are present in the crystal structure.

Related literature

For Schiff bases, see: Caligaris et al. (1972 ▶); Caligaris & Randaccio et al. (1987 ▶); Salman et al. (1990 ▶); Popović et al. (2001 ▶); Garnovskii et al. (1993 ▶); Pyrz et al. (1985 ▶); Hadjoudis et al. (1987 ▶). For the HOMA (harmonic oscillator model of aromaticity) index, see: Krygowski et al. (1993 ▶). For similar structures, see: Özek et al. (2004 ▶); Takano et al. (2009 ▶).

Experimental

Crystal data

C23H17NO2

M = 339.38

Monoclinic,

a = 14.6428 (11) Å

b = 5.6297 (3) Å

c = 42.602 (3) Å

β = 101.175 (6)°

V = 3445.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.34 × 0.23 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2002 ▶) T min = 0.960, T max = 0.996

11832 measured reflections

2565 independent reflections

1522 reflections with I > 2σ(I)

R int = 0.212

θmax = 23.6°

Refinement

R[F 2 > 2σ(F 2)] = 0.115

wR(F 2) = 0.331

S = 1.06

2565 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013851/si2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013851/si2256Isup2.hkl

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

C23H17NO2	F(000) = 1424
Mr = 339.38	Dx = 1.309 Mg m−3
Monoclinic, C2/c	Melting point = 411–413 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.6428 (11) Å	Cell parameters from 2565 reflections
b = 5.6297 (3) Å	θ = 2.8–24.1°
c = 42.602 (3) Å	µ = 0.08 mm−1
β = 101.175 (6)°	T = 296 K
V = 3445.3 (4) Å3	Long prismatic rod, yellow
Z = 8	0.40 × 0.34 × 0.23 mm

Stoe IPDSII diffractometer	2565 independent reflections
Radiation source: fine-focus sealed tube	1522 reflections with I > 2σ(I)
plane graphite	Rint = 0.212
Detector resolution: 6.67 pixels mm-1	θmax = 23.6°, θmin = 2.8°
rotation scans	h = −16→16
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −6→6
Tmin = 0.960, Tmax = 0.996	l = −47→47
11832 measured reflections

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)] = 0.115	H-atom parameters constrained
wR(F2) = 0.331	w = 1/[σ2(Fo2) + (0.1935P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2565 reflections	Δρmax = 0.30 e Å−3
236 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (17)

Experimental. 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.

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
C1	0.4850 (4)	−0.3268 (11)	0.56310 (14)	0.0576 (16)
C2	0.4649 (5)	−0.1907 (13)	0.53616 (18)	0.0748 (19)
H2	0.4969	−0.0499	0.5345	0.090*
C3	0.3949 (5)	−0.2683 (15)	0.51107 (16)	0.082 (2)
H3	0.3797	−0.1800	0.4923	0.099*
C4	0.3489 (4)	−0.4759 (13)	0.51444 (17)	0.075 (2)
H4	0.3040	−0.5314	0.4976	0.090*
C5	0.3683 (4)	−0.6017 (12)	0.54216 (17)	0.0704 (19)
H5	0.3345	−0.7383	0.5445	0.084*
C6	0.4377 (4)	−0.5276 (11)	0.56682 (15)	0.0641 (18)
H6	0.4517	−0.6144	0.5857	0.077*
C7	0.6418 (3)	−0.3294 (10)	0.59332 (14)	0.0513 (14)
C8	0.7060 (3)	−0.2112 (10)	0.61624 (13)	0.0482 (14)
C9	0.7982 (4)	−0.2933 (11)	0.62192 (15)	0.0581 (16)
H9	0.8429	−0.2158	0.6369	0.070*
C10	0.8231 (4)	−0.4821 (11)	0.60609 (16)	0.0622 (17)
H10	0.8845	−0.5343	0.6106	0.075*
C11	0.7588 (4)	−0.5997 (11)	0.58329 (15)	0.0627 (17)
H11	0.7767	−0.7284	0.5722	0.075*
C12	0.6665 (4)	−0.5216 (12)	0.57725 (15)	0.0639 (18)
H12	0.6220	−0.6002	0.5623	0.077*
C13	0.7229 (4)	0.1281 (10)	0.65264 (13)	0.0503 (14)
H13	0.7872	0.1090	0.6571	0.060*
C14	0.6860 (4)	0.3109 (9)	0.66784 (13)	0.0487 (14)
C15	0.5865 (4)	0.3495 (10)	0.66058 (15)	0.0571 (16)
C16	0.5513 (4)	0.5463 (12)	0.67467 (18)	0.0716 (19)
H16	0.4876	0.5747	0.6699	0.086*
C17	0.6065 (4)	0.6971 (12)	0.69492 (18)	0.0704 (19)
H17	0.5797	0.8235	0.7039	0.084*
C18	0.7048 (4)	0.6642 (10)	0.70262 (14)	0.0548 (15)
C19	0.7619 (5)	0.8288 (11)	0.72230 (14)	0.0647 (17)
H19	0.7347	0.9566	0.7308	0.078*
C20	0.8549 (5)	0.8045 (12)	0.72899 (16)	0.0730 (19)
H20	0.8916	0.9137	0.7422	0.088*
C21	0.8956 (5)	0.6163 (13)	0.71618 (17)	0.078 (2)
H21	0.9599	0.5976	0.7213	0.094*
C22	0.8435 (4)	0.4567 (12)	0.69608 (16)	0.0691 (19)
H22	0.8728	0.3352	0.6870	0.083*
C23	0.7448 (4)	0.4752 (9)	0.68896 (12)	0.0481 (14)
N1	0.6738 (3)	−0.0213 (8)	0.63234 (10)	0.0493 (12)
H1	0.6146	0.0005	0.6285	0.059*
O1	0.5318 (2)	0.2158 (8)	0.64128 (11)	0.0720 (14)
O2	0.5522 (2)	−0.2386 (8)	0.58887 (11)	0.0755 (15)

	U11	U22	U33	U12	U13	U23
C1	0.031 (3)	0.080 (4)	0.055 (4)	0.002 (3)	−0.008 (3)	−0.025 (3)
C2	0.060 (4)	0.084 (4)	0.075 (5)	−0.016 (3)	−0.001 (3)	−0.005 (4)
C3	0.072 (5)	0.116 (6)	0.050 (4)	−0.011 (4)	−0.010 (3)	0.007 (4)
C4	0.044 (3)	0.098 (5)	0.072 (5)	−0.011 (3)	−0.014 (3)	−0.016 (4)
C5	0.045 (3)	0.084 (4)	0.075 (5)	−0.010 (3)	−0.005 (3)	−0.007 (4)
C6	0.049 (3)	0.074 (4)	0.060 (4)	0.001 (3)	−0.013 (3)	−0.002 (3)
C7	0.028 (3)	0.066 (3)	0.055 (3)	0.000 (2)	−0.003 (2)	−0.011 (3)
C8	0.033 (3)	0.068 (3)	0.042 (3)	−0.005 (2)	0.003 (2)	−0.006 (3)
C9	0.031 (3)	0.075 (4)	0.062 (4)	−0.010 (3)	−0.007 (3)	0.001 (3)
C10	0.032 (3)	0.077 (4)	0.074 (4)	−0.003 (3)	0.003 (3)	−0.008 (3)
C11	0.043 (3)	0.080 (4)	0.064 (4)	0.001 (3)	0.008 (3)	−0.014 (3)
C12	0.033 (3)	0.093 (4)	0.061 (4)	−0.007 (3)	−0.002 (3)	−0.022 (3)
C13	0.033 (3)	0.071 (3)	0.043 (3)	0.000 (3)	−0.003 (2)	−0.001 (3)
C14	0.034 (3)	0.062 (3)	0.046 (3)	−0.003 (2)	−0.003 (2)	0.001 (3)
C15	0.029 (3)	0.069 (4)	0.069 (4)	−0.003 (3)	0.000 (3)	−0.001 (3)
C16	0.034 (3)	0.090 (5)	0.088 (5)	0.006 (3)	0.004 (3)	−0.012 (4)
C17	0.048 (3)	0.080 (4)	0.083 (5)	0.014 (3)	0.012 (3)	−0.004 (4)
C18	0.049 (3)	0.061 (3)	0.050 (3)	0.004 (3)	0.000 (3)	0.000 (3)
C19	0.073 (4)	0.065 (4)	0.050 (3)	0.008 (3)	−0.001 (3)	−0.008 (3)
C20	0.070 (4)	0.082 (4)	0.060 (4)	−0.009 (4)	−0.005 (3)	−0.013 (3)
C21	0.045 (3)	0.106 (5)	0.075 (5)	−0.004 (3)	−0.007 (3)	−0.021 (4)
C22	0.038 (3)	0.093 (4)	0.070 (4)	0.003 (3)	−0.007 (3)	−0.034 (3)
C23	0.041 (3)	0.058 (3)	0.040 (3)	0.003 (2)	−0.004 (2)	0.002 (2)
N1	0.027 (2)	0.071 (3)	0.045 (3)	−0.006 (2)	−0.0059 (19)	−0.006 (2)
O1	0.0240 (19)	0.097 (3)	0.087 (3)	−0.0049 (19)	−0.009 (2)	−0.018 (3)
O2	0.028 (2)	0.106 (3)	0.083 (3)	0.004 (2)	−0.013 (2)	−0.047 (3)

C1—C6	1.351 (9)	C12—H12	0.9300
C1—C2	1.364 (9)	C13—N1	1.315 (6)
C1—O2	1.414 (6)	C13—C14	1.381 (8)
C2—C3	1.400 (9)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.447 (7)
C3—C4	1.370 (10)	C14—C23	1.451 (7)
C3—H3	0.9300	C15—O1	1.276 (7)
C4—C5	1.359 (10)	C15—C16	1.404 (9)
C4—H4	0.9300	C16—C17	1.359 (9)
C5—C6	1.377 (8)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.425 (8)
C6—H6	0.9300	C17—H17	0.9300
C7—C12	1.366 (8)	C18—C23	1.395 (8)
C7—O2	1.387 (6)	C18—C19	1.411 (8)
C7—C8	1.387 (7)	C19—C20	1.344 (10)
C8—N1	1.400 (7)	C19—H19	0.9300
C8—C9	1.403 (8)	C20—C21	1.379 (10)
C9—C10	1.347 (9)	C20—H20	0.9300
C9—H9	0.9300	C21—C22	1.368 (8)
C10—C11	1.383 (8)	C21—H21	0.9300
C10—H10	0.9300	C22—C23	1.422 (8)
C11—C12	1.397 (8)	C22—H22	0.9300
C11—H11	0.9300	N1—H1	0.8600
C6—C1—C2	122.4 (5)	N1—C13—H13	117.6
C6—C1—O2	119.9 (6)	C14—C13—H13	117.6
C2—C1—O2	117.4 (6)	C13—C14—C15	118.8 (5)
C1—C2—C3	118.3 (7)	C13—C14—C23	121.8 (5)
C1—C2—H2	120.9	C15—C14—C23	119.3 (5)
C3—C2—H2	120.9	O1—C15—C16	120.3 (5)
C4—C3—C2	119.2 (7)	O1—C15—C14	122.0 (5)
C4—C3—H3	120.4	C16—C15—C14	117.7 (5)
C2—C3—H3	120.4	C17—C16—C15	122.9 (5)
C5—C4—C3	120.8 (6)	C17—C16—H16	118.6
C5—C4—H4	119.6	C15—C16—H16	118.6
C3—C4—H4	119.6	C16—C17—C18	120.9 (6)
C4—C5—C6	120.3 (6)	C16—C17—H17	119.5
C4—C5—H5	119.9	C18—C17—H17	119.5
C6—C5—H5	119.9	C23—C18—C19	120.0 (5)
C1—C6—C5	118.9 (6)	C23—C18—C17	119.4 (5)
C1—C6—H6	120.5	C19—C18—C17	120.5 (6)
C5—C6—H6	120.5	C20—C19—C18	121.3 (6)
C12—C7—O2	124.0 (5)	C20—C19—H19	119.4
C12—C7—C8	121.5 (5)	C18—C19—H19	119.4
O2—C7—C8	114.4 (5)	C19—C20—C21	119.5 (6)
C7—C8—N1	117.7 (5)	C19—C20—H20	120.2
C7—C8—C9	117.5 (5)	C21—C20—H20	120.2
N1—C8—C9	124.8 (5)	C22—C21—C20	121.4 (6)
C10—C9—C8	121.3 (5)	C22—C21—H21	119.3
C10—C9—H9	119.4	C20—C21—H21	119.3
C8—C9—H9	119.4	C21—C22—C23	120.4 (6)
C9—C10—C11	121.0 (6)	C21—C22—H22	119.8
C9—C10—H10	119.5	C23—C22—H22	119.8
C11—C10—H10	119.5	C18—C23—C22	117.3 (5)
C10—C11—C12	118.8 (6)	C18—C23—C14	119.9 (5)
C10—C11—H11	120.6	C22—C23—C14	122.8 (5)
C12—C11—H11	120.6	C13—N1—C8	128.1 (4)
C7—C12—C11	119.9 (5)	C13—N1—H1	115.9
C7—C12—H12	120.1	C8—N1—H1	115.9
C11—C12—H12	120.1	C7—O2—C1	118.3 (4)
N1—C13—C14	124.8 (5)
C6—C1—C2—C3	−2.5 (11)	C14—C15—C16—C17	−1.0 (11)
O2—C1—C2—C3	−176.5 (6)	C15—C16—C17—C18	1.0 (11)
C1—C2—C3—C4	0.3 (11)	C16—C17—C18—C23	0.4 (10)
C2—C3—C4—C5	2.4 (12)	C16—C17—C18—C19	176.6 (7)
C3—C4—C5—C6	−3.0 (11)	C23—C18—C19—C20	−1.8 (10)
C2—C1—C6—C5	1.9 (10)	C17—C18—C19—C20	−177.9 (7)
O2—C1—C6—C5	175.7 (6)	C18—C19—C20—C21	0.6 (11)
C4—C5—C6—C1	0.9 (10)	C19—C20—C21—C22	1.7 (12)
C12—C7—C8—N1	−177.8 (5)	C20—C21—C22—C23	−2.7 (12)
O2—C7—C8—N1	1.2 (8)	C19—C18—C23—C22	0.7 (9)
C12—C7—C8—C9	1.2 (9)	C17—C18—C23—C22	176.9 (6)
O2—C7—C8—C9	−179.8 (5)	C19—C18—C23—C14	−177.9 (5)
C7—C8—C9—C10	−1.0 (9)	C17—C18—C23—C14	−1.7 (9)
N1—C8—C9—C10	177.9 (6)	C21—C22—C23—C18	1.5 (10)
C8—C9—C10—C11	1.0 (10)	C21—C22—C23—C14	−180.0 (6)
C9—C10—C11—C12	−1.1 (10)	C13—C14—C23—C18	176.9 (5)
O2—C7—C12—C11	179.8 (6)	C15—C14—C23—C18	1.6 (8)
C8—C7—C12—C11	−1.4 (10)	C13—C14—C23—C22	−1.6 (9)
C10—C11—C12—C7	1.3 (10)	C15—C14—C23—C22	−176.9 (6)
N1—C13—C14—C15	−2.0 (9)	C14—C13—N1—C8	−179.5 (5)
N1—C13—C14—C23	−177.4 (5)	C7—C8—N1—C13	−173.3 (5)
C13—C14—C15—O1	2.0 (9)	C9—C8—N1—C13	7.7 (9)
C23—C14—C15—O1	177.4 (6)	C12—C7—O2—C1	−9.5 (10)
C13—C14—C15—C16	−175.8 (6)	C8—C7—O2—C1	171.6 (6)
C23—C14—C15—C16	−0.3 (9)	C6—C1—O2—C7	84.9 (8)
O1—C15—C16—C17	−178.8 (7)	C2—C1—O2—C7	−101.0 (7)

Cg1 and Cg2 are the centroids of the C1–C6 and C18–C23 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.87	2.561 (6)	136
C11—H11···Cg1i	0.93	2.87	3.664 (7)	144
C19—H19···Cg2ii	0.93	2.90	3.674 (7)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.87	2.561 (6)	136
C11—H11⋯Cg1i	0.93	2.87	3.664 (7)	144
C19—H19⋯Cg2ii	0.93	2.90	3.674 (7)	142

Symmetry codes: (i) ; (ii) .