Crystal structure of (E)-2-({[2-(1,3-dioxan-2-yl)phen-yl]imino}-meth-yl)phenol.

The title compound, C17H17NO3, prepared by the condensation reaction of 2-(1,3-dioxan-2-yl)aniline and salicyl-aldehyde, has an E conformation about the C=N bond. The six-membered O-heterocycle adopts a chair conformation, with the bond to the aromatic ring located at its equatorial position. The dihedral angle between the aromatic rings is 36.54 (9)°. There is an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along the a-axis direction. Within the chains, there are C-H⋯π inter-actions involving adjacent mol-ecules.

Related literature

For general background to acetals, see: Cismaş et al. (2005 ▸); Sun et al. (2010 ▸). For Schiff bases of salicyl­aldehyde having important applications in biological and pharmacological chemistry, see: Gupta & Sutar (2008 ▸); Jiménez-Sánchez et al. (2013 ▸). For further background to related Schiff base ligands and their various properties, see: Arod et al. (2005 ▸); Chatziefthimiou et al. (2006 ▸).

Experimental

Crystal data

C17H17NO3

M = 283.32

Orthorhombic,

a = 8.4873 (18) Å

b = 10.821 (2) Å

c = 16.232 (3) Å

V = 1490.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.978, T max = 0.981

9005 measured reflections

3123 independent reflections

2494 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.00

3123 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); 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/S2056989015008051/su5122sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008051/su5122Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015008051/su5122Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015008051/su5122fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% 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.

c . DOI: 10.1107/S2056989015008051/su5122fig2.tif

A partial view of the crystal packing of the title compound, view along the c axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1061272

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

C17H17NO3	F(000) = 600
Mr = 283.32	Dx = 1.262 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3792 reflections
a = 8.4873 (18) Å	θ = 2.3–26.4°
b = 10.821 (2) Å	µ = 0.09 mm−1
c = 16.232 (3) Å	T = 296 K
V = 1490.8 (5) Å3	Block, yellow
Z = 4	0.26 × 0.24 × 0.22 mm

Bruker APEXII CCD area-detector diffractometer	3123 independent reflections
Radiation source: fine-focus sealed tube	2494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
phi and ω scans	θmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
Tmin = 0.978, Tmax = 0.981	k = −13→13
9005 measured reflections	l = −17→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.020P] where P = (Fo2 + 2Fc2)/3
3123 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.21 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
C1	0.36289 (19)	0.02306 (15)	0.41243 (12)	0.0456 (4)
C2	0.4402 (2)	0.0087 (2)	0.48668 (13)	0.0594 (5)
H2	0.4360	−0.0668	0.5140	0.071*
C3	0.5234 (3)	0.1054 (2)	0.52064 (14)	0.0666 (6)
H3	0.5749	0.0945	0.5707	0.080*
C4	0.5314 (2)	0.2185 (2)	0.48125 (14)	0.0645 (5)
H4	0.5872	0.2835	0.5047	0.077*
C5	0.4561 (2)	0.23357 (17)	0.40717 (14)	0.0567 (5)
H5	0.4616	0.3096	0.3807	0.068*
C6	0.37108 (19)	0.13744 (15)	0.37051 (12)	0.0442 (4)
C7	0.2987 (2)	0.15509 (15)	0.29062 (12)	0.0455 (4)
H7	0.3059	0.2324	0.2659	0.055*
C8	0.16825 (19)	0.09047 (14)	0.17144 (11)	0.0409 (4)
C9	0.2536 (2)	0.16144 (17)	0.11485 (13)	0.0507 (4)
H9	0.3494	0.1962	0.1303	0.061*
C10	0.1966 (2)	0.18018 (19)	0.03623 (13)	0.0572 (5)
H10	0.2533	0.2288	−0.0005	0.069*
C11	0.0567 (2)	0.12752 (18)	0.01177 (12)	0.0549 (5)
H11	0.0185	0.1407	−0.0412	0.066*
C12	−0.0266 (2)	0.05486 (16)	0.06659 (12)	0.0482 (4)
H12	−0.1208	0.0188	0.0499	0.058*
C13	0.02793 (18)	0.03466 (13)	0.14640 (10)	0.0390 (3)
C14	−0.06859 (19)	−0.03996 (13)	0.20547 (11)	0.0415 (4)
H14	0.0019	−0.0855	0.2424	0.050*
C15	−0.2564 (3)	−0.0245 (2)	0.31050 (16)	0.0704 (6)
H15A	−0.3223	0.0334	0.3404	0.084*
H15B	−0.1891	−0.0664	0.3499	0.084*
C16	−0.3585 (2)	−0.1176 (2)	0.26691 (17)	0.0710 (6)
H16A	−0.4128	−0.1685	0.3071	0.085*
H16B	−0.4371	−0.0752	0.2340	0.085*
C17	−0.2593 (3)	−0.1966 (2)	0.21304 (19)	0.0797 (7)
H17A	−0.1945	−0.2500	0.2470	0.096*
H17B	−0.3267	−0.2486	0.1794	0.096*
N1	0.22509 (16)	0.06900 (12)	0.25250 (9)	0.0427 (3)
O1	0.28135 (16)	−0.07360 (11)	0.38050 (9)	0.0606 (4)
H1	0.2368	−0.0545	0.3354	0.091*
O2	−0.16132 (15)	0.04108 (10)	0.25196 (9)	0.0536 (3)
O3	−0.16055 (18)	−0.12428 (12)	0.16085 (10)	0.0670 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (9)	0.0476 (8)	0.0479 (9)	−0.0025 (7)	0.0094 (8)	0.0012 (7)
C2	0.0610 (11)	0.0654 (11)	0.0517 (11)	−0.0032 (10)	0.0004 (9)	0.0117 (10)
C3	0.0688 (13)	0.0826 (14)	0.0484 (11)	−0.0044 (11)	−0.0071 (10)	0.0028 (11)
C4	0.0687 (12)	0.0662 (11)	0.0586 (13)	−0.0109 (10)	−0.0074 (10)	−0.0122 (10)
C5	0.0586 (11)	0.0474 (9)	0.0642 (12)	−0.0064 (8)	−0.0016 (10)	−0.0024 (9)
C6	0.0400 (8)	0.0445 (8)	0.0480 (9)	0.0015 (7)	0.0043 (8)	−0.0020 (7)
C7	0.0459 (9)	0.0382 (7)	0.0525 (10)	−0.0014 (7)	0.0030 (8)	0.0037 (7)
C8	0.0410 (8)	0.0364 (7)	0.0452 (9)	−0.0001 (6)	0.0038 (7)	0.0011 (7)
C9	0.0460 (9)	0.0530 (9)	0.0531 (11)	−0.0096 (8)	0.0056 (8)	0.0053 (8)
C10	0.0583 (11)	0.0591 (10)	0.0542 (11)	−0.0029 (9)	0.0128 (9)	0.0105 (8)
C11	0.0559 (11)	0.0643 (11)	0.0446 (10)	0.0081 (9)	0.0046 (8)	0.0013 (9)
C12	0.0428 (9)	0.0521 (9)	0.0496 (10)	0.0037 (7)	0.0009 (8)	−0.0063 (8)
C13	0.0376 (8)	0.0335 (7)	0.0460 (9)	0.0031 (6)	0.0042 (7)	−0.0044 (6)
C14	0.0361 (8)	0.0364 (7)	0.0519 (9)	0.0016 (6)	0.0014 (7)	0.0004 (7)
C15	0.0669 (13)	0.0810 (14)	0.0632 (14)	−0.0131 (12)	0.0203 (11)	−0.0020 (12)
C16	0.0464 (10)	0.0842 (13)	0.0824 (16)	−0.0132 (10)	0.0135 (11)	0.0118 (13)
C17	0.0778 (15)	0.0588 (11)	0.103 (2)	−0.0284 (11)	0.0238 (14)	−0.0027 (13)
N1	0.0381 (7)	0.0429 (6)	0.0470 (8)	−0.0035 (5)	0.0011 (7)	0.0035 (6)
O1	0.0697 (8)	0.0510 (6)	0.0612 (8)	−0.0186 (6)	−0.0049 (7)	0.0099 (7)
O2	0.0570 (7)	0.0468 (6)	0.0570 (7)	−0.0036 (5)	0.0189 (6)	−0.0069 (6)
O3	0.0723 (9)	0.0561 (7)	0.0726 (10)	−0.0275 (7)	0.0215 (8)	−0.0191 (7)

C1—O1	1.357 (2)	C10—H10	0.9300
C1—C2	1.381 (3)	C11—C12	1.382 (3)
C1—C6	1.414 (2)	C11—H11	0.9300
C2—C3	1.378 (3)	C12—C13	1.393 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.382 (3)	C13—C14	1.497 (2)
C3—H3	0.9300	C14—O2	1.399 (2)
C4—C5	1.372 (3)	C14—O3	1.402 (2)
C4—H4	0.9300	C14—H14	0.9800
C5—C6	1.399 (3)	C15—O2	1.435 (2)
C5—H5	0.9300	C15—C16	1.505 (3)
C6—C7	1.448 (3)	C15—H15A	0.9700
C7—N1	1.281 (2)	C15—H15B	0.9700
C7—H7	0.9300	C16—C17	1.485 (3)
C8—C13	1.396 (2)	C16—H16A	0.9700
C8—C9	1.399 (2)	C16—H16B	0.9700
C8—N1	1.420 (2)	C17—O3	1.426 (3)
C9—C10	1.380 (3)	C17—H17A	0.9700
C9—H9	0.9300	C17—H17B	0.9700
C10—C11	1.375 (3)	O1—H1	0.8501
O1—C1—C2	119.27 (16)	C11—C12—H12	119.4
O1—C1—C6	121.05 (17)	C13—C12—H12	119.4
C2—C1—C6	119.67 (17)	C12—C13—C8	119.10 (15)
C3—C2—C1	120.50 (19)	C12—C13—C14	119.90 (14)
C3—C2—H2	119.8	C8—C13—C14	120.91 (15)
C1—C2—H2	119.8	O2—C14—O3	111.92 (14)
C2—C3—C4	120.8 (2)	O2—C14—C13	108.36 (11)
C2—C3—H3	119.6	O3—C14—C13	108.94 (15)
C4—C3—H3	119.6	O2—C14—H14	109.2
C5—C4—C3	119.21 (19)	O3—C14—H14	109.2
C5—C4—H4	120.4	C13—C14—H14	109.2
C3—C4—H4	120.4	O2—C15—C16	110.1 (2)
C4—C5—C6	121.66 (19)	O2—C15—H15A	109.6
C4—C5—H5	119.2	C16—C15—H15A	109.6
C6—C5—H5	119.2	O2—C15—H15B	109.6
C5—C6—C1	118.13 (17)	C16—C15—H15B	109.6
C5—C6—C7	120.13 (16)	H15A—C15—H15B	108.2
C1—C6—C7	121.71 (15)	C17—C16—C15	109.61 (17)
N1—C7—C6	122.95 (15)	C17—C16—H16A	109.7
N1—C7—H7	118.5	C15—C16—H16A	109.7
C6—C7—H7	118.5	C17—C16—H16B	109.7
C13—C8—C9	119.22 (16)	C15—C16—H16B	109.7
C13—C8—N1	119.25 (14)	H16A—C16—H16B	108.2
C9—C8—N1	121.46 (15)	O3—C17—C16	111.56 (16)
C10—C9—C8	120.40 (18)	O3—C17—H17A	109.3
C10—C9—H9	119.8	C16—C17—H17A	109.3
C8—C9—H9	119.8	O3—C17—H17B	109.3
C11—C10—C9	120.59 (18)	C16—C17—H17B	109.3
C11—C10—H10	119.7	H17A—C17—H17B	108.0
C9—C10—H10	119.7	C7—N1—C8	119.61 (14)
C10—C11—C12	119.44 (19)	C1—O1—H1	111.6
C10—C11—H11	120.3	C14—O2—C15	111.33 (13)
C12—C11—H11	120.3	C14—O3—C17	112.17 (17)
C11—C12—C13	121.21 (17)
O1—C1—C2—C3	−179.79 (19)	C9—C8—C13—C12	−2.4 (2)
C6—C1—C2—C3	0.8 (3)	N1—C8—C13—C12	−179.32 (15)
C1—C2—C3—C4	0.0 (3)	C9—C8—C13—C14	−178.78 (15)
C2—C3—C4—C5	−0.4 (3)	N1—C8—C13—C14	4.3 (2)
C3—C4—C5—C6	0.1 (3)	C12—C13—C14—O2	−94.14 (18)
C4—C5—C6—C1	0.7 (3)	C8—C13—C14—O2	82.23 (17)
C4—C5—C6—C7	−177.36 (18)	C12—C13—C14—O3	27.85 (19)
O1—C1—C6—C5	179.50 (15)	C8—C13—C14—O3	−155.78 (15)
C2—C1—C6—C5	−1.1 (2)	O2—C15—C16—C17	52.4 (3)
O1—C1—C6—C7	−2.5 (3)	C15—C16—C17—O3	−51.1 (3)
C2—C1—C6—C7	176.88 (16)	C6—C7—N1—C8	−174.91 (15)
C5—C6—C7—N1	177.01 (16)	C13—C8—N1—C7	−146.14 (15)
C1—C6—C7—N1	−1.0 (3)	C9—C8—N1—C7	37.0 (2)
C13—C8—C9—C10	2.6 (3)	O3—C14—O2—C15	60.3 (2)
N1—C8—C9—C10	179.47 (18)	C13—C14—O2—C15	−179.59 (16)
C8—C9—C10—C11	−1.3 (3)	C16—C15—O2—C14	−57.2 (2)
C9—C10—C11—C12	−0.3 (3)	O2—C14—O3—C17	−58.6 (2)
C10—C11—C12—C13	0.5 (3)	C13—C14—O3—C17	−178.37 (16)
C11—C12—C13—C8	0.9 (2)	C16—C17—O3—C14	54.4 (3)
C11—C12—C13—C14	177.32 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85	1.90	2.632 (2)	144
C7—H7···O2i	0.93	2.48	3.364 (2)	160
C15—H15A···Cg1ii	0.97	2.77	3.694 (3)	160

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
O1H1N1	0.85	1.90	2.632(2)	144
C7H7O2i	0.93	2.48	3.364(2)	160
C15H15A Cg1ii	0.97	2.77	3.694(3)	160

Symmetry codes: (i) ; (ii) .