Crystal structure of (E)-1-{[(3,5-di-methyl-phen-yl)imino]-meth-yl}naphthalen-2-ol.

The title compound, C19H17NO, has an E conformation about the N=C bond. The mol-ecule is relatively planar, with the benzene ring and naphthalene ring plane being inclined to one another by 4.28 (10)°. There is an intra-molecular O-H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains propagating along [100]. Within the chains there are π-π inter-actions involving the benzene ring and the naphthalene ring system of an adjacent mol-ecule [inter-centroid distance = 3.6405 (14) Å].

Related literature

For the diverse applications and biological activities of Schiff bases, see: Schiff (1864 ▸); Dutta & Das (1988 ▸); Chandra & Sangeetika (2004 ▸); Cozzi (2004 ▸). For the biological activity and optical properties of Schiff bases derived from 2-hy­droxy­napthaldehyde, see: Abdel-Rahman et al. (2013a ▸,b ▸, 2014 ▸); Abu-Dief et al. (2013 ▸).

Experimental

Crystal data

C19H17NO

M = 275.33

Orthorhombic,

a = 6.2463 (2) Å

b = 10.2438 (3) Å

c = 23.0533 (8) Å

V = 1475.08 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 293 K

0.73 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▸) T min = 0.915, T max = 0.94

8103 measured reflections

2834 independent reflections

1422 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.09

1649 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▸); program(s) used to solve structure: SIR2011 (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011548/su5133sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011548/su5133Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015011548/su5133Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015011548/su5133fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intra­molecular O—H⋯N hydrogen bond is shown as a dashed line (see Table 1 for details).

Click here for additional data file.

b . DOI: 10.1107/S2056989015011548/su5133fig2.tif

A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). H atoms not involved in these inter­actions have been omitted for clarity.

CCDC reference: 1406684

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H17NO	Dx = 1.240 Mg m−3
Mr = 275.33	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 2417 reflections
a = 6.2463 (2) Å	θ = 3.8–69.9°
b = 10.2438 (3) Å	µ = 0.60 mm−1
c = 23.0533 (8) Å	T = 293 K
V = 1475.08 (8) Å3	Prism, colourless
Z = 4	0.73 × 0.12 × 0.09 mm
F(000) = 584

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer	2834 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.2673 pixels mm-1	θmax = 70.4°, θmin = 3.8°
ω scans	h = −7→6
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.915, Tmax = 0.94	l = −27→28
8103 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.0057P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
1649 reflections	Δρmax = 0.17 e Å−3
193 parameters	Δρmin = −0.14 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.

	x	y	z	Uiso*/Ueq
O1	0.6500 (4)	0.7247 (2)	0.05918 (10)	0.0874 (7)
H1	0.7473	0.6710	0.0584	0.131*
N1	0.8802 (3)	0.53539 (18)	0.09101 (9)	0.0551 (5)
C1	0.5709 (3)	0.6003 (2)	0.14386 (10)	0.0511 (5)
C2	0.5267 (4)	0.7006 (2)	0.10264 (13)	0.0641 (7)
C3	0.3348 (5)	0.7757 (2)	0.10869 (14)	0.0740 (8)
H3	0.3038	0.8404	0.0817	0.089*
C4	0.1983 (4)	0.7542 (3)	0.15291 (13)	0.0703 (7)
H4	0.0740	0.8040	0.1554	0.084*
C5	0.0928 (5)	0.6360 (3)	0.24126 (13)	0.0712 (7)
H5	−0.0293	0.6877	0.2437	0.085*
C6	0.1263 (5)	0.5409 (3)	0.28162 (13)	0.0794 (8)
H6	0.0271	0.5275	0.3111	0.095*
C7	0.3088 (5)	0.4643 (3)	0.27857 (12)	0.0728 (7)
H7	0.3322	0.3997	0.3062	0.087*
C8	0.4552 (4)	0.4833 (3)	0.23502 (11)	0.0614 (6)
H8	0.5772	0.4314	0.2338	0.074*
C9	0.4256 (4)	0.5796 (2)	0.19192 (10)	0.0524 (5)
C10	0.2386 (4)	0.6573 (2)	0.19625 (11)	0.0577 (6)
C11	0.7513 (4)	0.5198 (2)	0.13492 (10)	0.0508 (5)
H11	0.7791	0.4533	0.1613	0.061*
C12	1.0636 (4)	0.4608 (2)	0.07758 (10)	0.0516 (5)
C13	1.1710 (4)	0.4957 (2)	0.02723 (11)	0.0590 (6)
H13	1.1194	0.5640	0.0046	0.071*
C14	1.3542 (4)	0.4297 (2)	0.01026 (12)	0.0639 (6)
C15	1.4288 (4)	0.3287 (2)	0.04512 (12)	0.0644 (7)
H15	1.5511	0.2834	0.0340	0.077*
C16	1.3257 (4)	0.2940 (2)	0.09578 (12)	0.0599 (6)
C17	1.1405 (4)	0.3596 (2)	0.11176 (11)	0.0562 (6)
H17	1.0680	0.3359	0.1454	0.067*
C18	1.4130 (5)	0.1868 (3)	0.13355 (14)	0.0790 (8)
H18A	1.5003	0.1295	0.1106	0.119*
H18B	1.2965	0.1383	0.1501	0.119*
H18C	1.4979	0.2241	0.1640	0.119*
C19	1.4706 (6)	0.4694 (3)	−0.04430 (15)	0.0950 (11)
H19A	1.4351	0.5581	−0.0538	0.142*
H19B	1.4286	0.4132	−0.0756	0.142*
H19C	1.6222	0.4622	−0.0382	0.142*

	U11	U22	U33	U12	U13	U23
O1	0.0695 (12)	0.0857 (13)	0.1071 (15)	0.0178 (11)	0.0232 (13)	0.0409 (12)
N1	0.0420 (9)	0.0567 (9)	0.0667 (11)	0.0027 (9)	0.0022 (10)	0.0052 (8)
C1	0.0410 (10)	0.0505 (10)	0.0618 (13)	−0.0015 (9)	−0.0034 (11)	−0.0022 (9)
C2	0.0518 (13)	0.0585 (12)	0.0819 (17)	0.0050 (12)	0.0038 (14)	0.0120 (12)
C3	0.0656 (15)	0.0588 (13)	0.098 (2)	0.0161 (14)	0.0032 (18)	0.0149 (13)
C4	0.0542 (13)	0.0616 (13)	0.095 (2)	0.0151 (12)	0.0018 (15)	−0.0004 (13)
C5	0.0516 (13)	0.0851 (17)	0.0770 (17)	0.0037 (13)	0.0034 (14)	−0.0138 (14)
C6	0.0640 (16)	0.106 (2)	0.0685 (17)	−0.0055 (18)	0.0119 (15)	−0.0069 (16)
C7	0.0659 (16)	0.0889 (18)	0.0638 (15)	−0.0074 (16)	0.0016 (14)	0.0051 (13)
C8	0.0529 (13)	0.0698 (13)	0.0616 (14)	0.0036 (12)	−0.0019 (12)	0.0015 (11)
C9	0.0438 (11)	0.0546 (11)	0.0587 (13)	−0.0040 (10)	−0.0046 (11)	−0.0066 (10)
C10	0.0457 (11)	0.0606 (12)	0.0668 (15)	0.0009 (11)	−0.0022 (12)	−0.0110 (11)
C11	0.0428 (10)	0.0513 (10)	0.0583 (13)	−0.0011 (9)	−0.0034 (10)	0.0025 (10)
C12	0.0405 (10)	0.0494 (10)	0.0648 (14)	−0.0027 (10)	−0.0009 (10)	−0.0009 (9)
C13	0.0590 (14)	0.0536 (10)	0.0645 (13)	0.0000 (11)	0.0065 (13)	0.0035 (10)
C14	0.0592 (14)	0.0570 (12)	0.0757 (16)	−0.0041 (12)	0.0136 (14)	−0.0058 (11)
C15	0.0512 (13)	0.0542 (11)	0.0877 (18)	0.0019 (11)	0.0070 (14)	−0.0090 (12)
C16	0.0475 (12)	0.0523 (11)	0.0801 (16)	−0.0003 (11)	−0.0040 (14)	−0.0031 (11)
C17	0.0474 (11)	0.0554 (11)	0.0658 (14)	−0.0006 (11)	−0.0007 (12)	0.0042 (10)
C18	0.0670 (16)	0.0714 (15)	0.099 (2)	0.0149 (14)	−0.0076 (17)	0.0115 (14)
C19	0.096 (2)	0.0869 (18)	0.102 (2)	0.0041 (19)	0.046 (2)	0.0044 (17)

O1—C2	1.287 (3)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.417 (3)
N1—C11	1.304 (3)	C11—H11	0.9300
N1—C12	1.411 (3)	C12—C13	1.387 (3)
C1—C11	1.411 (3)	C12—C17	1.388 (3)
C1—C2	1.427 (3)	C13—C14	1.385 (3)
C1—C9	1.448 (3)	C13—H13	0.9300
C2—C3	1.431 (4)	C14—C15	1.391 (4)
C3—C4	1.347 (4)	C14—C19	1.509 (4)
C3—H3	0.9300	C15—C16	1.380 (4)
C4—C10	1.431 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.388 (3)
C5—C6	1.363 (4)	C16—C18	1.504 (3)
C5—C10	1.398 (4)	C17—H17	0.9300
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.386 (4)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—C8	1.372 (4)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C9	1.412 (3)	C19—H19C	0.9600
C2—O1—H1	109.5	N1—C11—H11	118.8
C11—N1—C12	127.3 (2)	C1—C11—H11	118.8
C11—C1—C2	118.6 (2)	C13—C12—C17	120.0 (2)
C11—C1—C9	121.8 (2)	C13—C12—N1	115.9 (2)
C2—C1—C9	119.6 (2)	C17—C12—N1	124.1 (2)
O1—C2—C1	122.7 (2)	C14—C13—C12	120.7 (2)
O1—C2—C3	118.3 (2)	C14—C13—H13	119.7
C1—C2—C3	119.0 (2)	C12—C13—H13	119.7
C4—C3—C2	121.1 (2)	C13—C14—C15	118.5 (2)
C4—C3—H3	119.5	C13—C14—C19	120.1 (3)
C2—C3—H3	119.5	C15—C14—C19	121.4 (2)
C3—C4—C10	122.0 (2)	C16—C15—C14	121.6 (2)
C3—C4—H4	119.0	C16—C15—H15	119.2
C10—C4—H4	119.0	C14—C15—H15	119.2
C6—C5—C10	121.2 (3)	C15—C16—C17	119.2 (2)
C6—C5—H5	119.4	C15—C16—C18	120.6 (2)
C10—C5—H5	119.4	C17—C16—C18	120.2 (3)
C5—C6—C7	119.8 (3)	C16—C17—C12	120.0 (2)
C5—C6—H6	120.1	C16—C17—H17	120.0
C7—C6—H6	120.1	C12—C17—H17	120.0
C8—C7—C6	120.3 (3)	C16—C18—H18A	109.5
C8—C7—H7	119.8	C16—C18—H18B	109.5
C6—C7—H7	119.8	H18A—C18—H18B	109.5
C7—C8—C9	121.8 (2)	C16—C18—H18C	109.5
C7—C8—H8	119.1	H18A—C18—H18C	109.5
C9—C8—H8	119.1	H18B—C18—H18C	109.5
C8—C9—C10	116.8 (2)	C14—C19—H19A	109.5
C8—C9—C1	124.0 (2)	C14—C19—H19B	109.5
C10—C9—C1	119.2 (2)	H19A—C19—H19B	109.5
C5—C10—C9	120.1 (2)	C14—C19—H19C	109.5
C5—C10—C4	120.8 (2)	H19A—C19—H19C	109.5
C9—C10—C4	119.1 (2)	H19B—C19—H19C	109.5
N1—C11—C1	122.4 (2)
C11—C1—C2—O1	−3.3 (4)	C1—C9—C10—C4	0.0 (3)
C9—C1—C2—O1	179.5 (2)	C3—C4—C10—C5	−179.2 (3)
C11—C1—C2—C3	174.9 (2)	C3—C4—C10—C9	−1.3 (4)
C9—C1—C2—C3	−2.2 (4)	C12—N1—C11—C1	−179.6 (2)
O1—C2—C3—C4	179.3 (3)	C2—C1—C11—N1	1.2 (3)
C1—C2—C3—C4	1.0 (4)	C9—C1—C11—N1	178.2 (2)
C2—C3—C4—C10	0.8 (4)	C11—N1—C12—C13	178.5 (2)
C10—C5—C6—C7	0.6 (4)	C11—N1—C12—C17	−2.8 (4)
C5—C6—C7—C8	−0.3 (4)	C17—C12—C13—C14	0.6 (4)
C6—C7—C8—C9	−0.5 (4)	N1—C12—C13—C14	179.4 (2)
C7—C8—C9—C10	0.9 (4)	C12—C13—C14—C15	−0.6 (4)
C7—C8—C9—C1	−177.6 (2)	C12—C13—C14—C19	−179.4 (3)
C11—C1—C9—C8	3.1 (3)	C13—C14—C15—C16	−0.4 (4)
C2—C1—C9—C8	−179.8 (2)	C19—C14—C15—C16	178.4 (3)
C11—C1—C9—C10	−175.3 (2)	C14—C15—C16—C17	1.4 (4)
C2—C1—C9—C10	1.7 (3)	C14—C15—C16—C18	−178.3 (3)
C6—C5—C10—C9	−0.1 (4)	C15—C16—C17—C12	−1.4 (3)
C6—C5—C10—C4	177.8 (3)	C18—C16—C17—C12	178.3 (2)
C8—C9—C10—C5	−0.6 (3)	C13—C12—C17—C16	0.4 (3)
C1—C9—C10—C5	177.9 (2)	N1—C12—C17—C16	−178.3 (2)
C8—C9—C10—C4	−178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.523 (3)	149
C13—H13···O1i	0.93	2.62	3.492 (3)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.78	2.523(3)	149
C13H13O1i	0.93	2.62	3.492(3)	156

Symmetry code: (i) .