2-(2-Naphth-yl)-1,3-dioxane.

The title compound, C(14)H(14)O(2), crystallizes in the chiral monoclinic space group P2(1). This acetal is composed of a planar naphthalene ring with a 1,3-dioxane ring substituent, which has a chair conformation. In the crystal structure, symmetry-related mol-ecules are connected via a weak C-H⋯O inter-action to form a helical chain propagating in [010]. While there are no π-π stacking inter-actions present, there are weak C-H⋯π inter-actions involving the naphthalene aromatic rings, which link the helical chains to form a two-dimensional network in the (011) plane.

Related literature

For information on commonly used protecting groups for carbonyl compounds, see: Kocienski (1994 ▶); Showler & Darley (1967 ▶). For methods for their deprotection, see: Cordes & Bull (1974 ▶); Fujioka et al. (2004 ▶); Ates et al. (2003 ▶). For kinetic and thermodynamic studies of acetals and ketals in the naphthalene series and other physical data, see: Newman & Dickson (1970 ▶); Carmichael & Hug (1986 ▶). For the synthesis of 2-naphthaldehyde acetal, see Gopinath et al. (2002 ▶). For details of the new photochemical reaction to hydrolyse the acetal into an aldehyde, see Thevenet & Neier (2010 ▶). For information on 1,3-dioxane ring related compounds, see: Buys & Eliel (1970 ▶). For the synthesis and crystal structure of a related compound, see: Borbas et al. (2002 ▶). For normal geometric parameters for mol­ecular compounds, see: Allen (2002 ▶).

Experimental

Crystal data

C14H14O2

M = 214.25

Monoclinic,

a = 7.5351 (6) Å

b = 7.8575 (8) Å

c = 9.4057 (9) Å

β = 92.839 (11)°

V = 556.20 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.38 × 0.30 × 0.08 mm

Data collection

Stoe IPDS diffractometer

4461 measured reflections

1098 independent reflections

951 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.061

S = 1.05

1098 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.11 e Å−3

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000644/cv2685sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000644/cv2685Isup2.hkl

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

C14H14O2	F(000) = 228
Mr = 214.25	Dx = 1.279 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4553 reflections
a = 7.5351 (6) Å	θ = 2.1–26.0°
b = 7.8575 (8) Å	µ = 0.08 mm−1
c = 9.4057 (9) Å	T = 173 K
β = 92.839 (11)°	Plate, colourless
V = 556.20 (9) Å3	0.38 × 0.30 × 0.08 mm
Z = 2

Stoe IPDS diffractometer	951 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 26.0°, θmin = 2.2°
φ rotation scans	h = −8→8
4461 measured reflections	k = −9→9
1098 independent reflections	l = −11→11

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
1098 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.11 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. In the final cycles of refinement, in the absence of significant anomalous scattering effects, 944 (93%) Friedel pairs were merged and Δf " set to zero. The H-atoms could all be located in difference electron-density maps. In the final cycles of refinement they were included in calculated positions and treated as riding atoms: C—H = 0.95 - 1.0 Å, with Uiso(H) = 1.2Ueq(parent C-atoms). Using the one-circle Stoe Image Plate Diffraction System it is not always possible to measure 100% of the Ewald sphere, and here only 93.7% of the data were accessible out to 50° in 2θ.

	x	y	z	Uiso*/Ueq
O2	1.16506 (19)	0.57058 (16)	0.43163 (12)	0.0337 (4)
O6	1.33418 (18)	0.38156 (15)	0.57014 (12)	0.0295 (4)
C1	1.1616 (2)	0.4392 (2)	0.53276 (17)	0.0251 (5)
C1'	0.9100 (2)	0.46504 (19)	0.69218 (16)	0.0239 (5)
C2'	1.0796 (2)	0.5075 (2)	0.66364 (16)	0.0240 (5)
C3	1.2305 (3)	0.5057 (3)	0.30168 (18)	0.0417 (7)
C3'	1.1796 (3)	0.6163 (2)	0.75664 (17)	0.0277 (6)
C4	1.4131 (3)	0.4321 (3)	0.32815 (19)	0.0400 (7)
C4'	1.1073 (3)	0.6764 (2)	0.87667 (18)	0.0297 (6)
C5	1.4128 (3)	0.3067 (3)	0.44944 (18)	0.0348 (6)
C5'	0.8555 (3)	0.6908 (2)	1.03543 (18)	0.0309 (6)
C6'	0.6865 (3)	0.6467 (2)	1.06380 (18)	0.0316 (6)
C7'	0.5852 (3)	0.5438 (2)	0.96939 (18)	0.0328 (6)
C8'	0.6551 (2)	0.4853 (2)	0.84779 (18)	0.0284 (5)
C9'	0.8310 (2)	0.52609 (19)	0.81562 (16)	0.0236 (5)
C10'	0.9334 (2)	0.63231 (19)	0.91039 (17)	0.0239 (5)
H1	1.08840	0.34250	0.49320	0.0300*
H1'	0.84350	0.39320	0.62810	0.0290*
H3'	1.29720	0.64750	0.73540	0.0330*
H3A	1.14900	0.41670	0.26250	0.0500*
H3E	1.23480	0.59870	0.23090	0.0500*
H4'	1.17550	0.74940	0.93860	0.0360*
H4A	1.45060	0.37410	0.24110	0.0480*
H4E	1.49890	0.52450	0.35160	0.0480*
H5'	0.92210	0.76160	1.10020	0.0370*
H5A	1.53630	0.27170	0.47590	0.0420*
H5E	1.34500	0.20400	0.41910	0.0420*
H6'	0.63660	0.68620	1.14860	0.0380*
H7'	0.46700	0.51460	0.99020	0.0390*
H8'	0.58470	0.41640	0.78400	0.0340*

	U11	U22	U33	U12	U13	U23
O2	0.0500 (9)	0.0289 (6)	0.0225 (6)	0.0088 (6)	0.0049 (5)	0.0012 (5)
O6	0.0283 (8)	0.0376 (7)	0.0228 (5)	0.0058 (6)	0.0027 (5)	−0.0007 (5)
C1	0.0269 (11)	0.0239 (8)	0.0244 (8)	−0.0013 (6)	0.0008 (7)	0.0000 (6)
C1'	0.0245 (11)	0.0228 (8)	0.0240 (8)	−0.0016 (6)	−0.0023 (7)	0.0007 (6)
C2'	0.0265 (11)	0.0229 (8)	0.0225 (8)	−0.0003 (7)	0.0012 (7)	0.0021 (7)
C3	0.0679 (17)	0.0358 (9)	0.0220 (8)	0.0095 (10)	0.0084 (9)	0.0013 (8)
C3'	0.0224 (11)	0.0303 (9)	0.0307 (9)	−0.0050 (7)	0.0031 (7)	−0.0032 (7)
C4	0.0533 (16)	0.0374 (10)	0.0306 (9)	−0.0015 (9)	0.0158 (9)	−0.0061 (8)
C4'	0.0273 (12)	0.0299 (9)	0.0317 (9)	−0.0050 (7)	−0.0007 (7)	−0.0058 (7)
C5	0.0371 (13)	0.0395 (10)	0.0283 (9)	0.0069 (8)	0.0077 (8)	−0.0053 (8)
C5'	0.0345 (14)	0.0286 (9)	0.0298 (9)	0.0016 (7)	0.0026 (8)	−0.0023 (7)
C6'	0.0322 (12)	0.0327 (9)	0.0309 (8)	0.0066 (8)	0.0105 (7)	0.0024 (7)
C7'	0.0230 (12)	0.0382 (11)	0.0377 (9)	0.0031 (7)	0.0063 (8)	0.0075 (8)
C8'	0.0222 (11)	0.0316 (9)	0.0313 (8)	−0.0035 (8)	0.0004 (7)	0.0029 (7)
C9'	0.0222 (11)	0.0226 (8)	0.0257 (8)	0.0007 (6)	−0.0005 (7)	0.0051 (6)
C10'	0.0242 (11)	0.0211 (7)	0.0264 (8)	0.0010 (7)	0.0013 (7)	0.0007 (6)

O2—C1	1.405 (2)	C8'—C9'	1.411 (2)
O2—C3	1.434 (2)	C9'—C10'	1.421 (2)
O6—C1	1.405 (2)	C1—H1	1.0000
O6—C5	1.433 (2)	C1'—H1'	0.9500
C1—C2'	1.504 (2)	C3—H3A	0.9900
C1'—C2'	1.360 (2)	C3—H3E	0.9900
C1'—C9'	1.415 (2)	C3'—H3'	0.9500
C2'—C3'	1.414 (2)	C4—H4A	0.9900
C3—C4	1.502 (3)	C4—H4E	0.9900
C3'—C4'	1.362 (3)	C4'—H4'	0.9500
C4—C5	1.508 (3)	C5—H5A	0.9900
C4'—C10'	1.407 (3)	C5—H5E	0.9900
C5'—C6'	1.359 (3)	C5'—H5'	0.9500
C5'—C10'	1.417 (2)	C6'—H6'	0.9500
C6'—C7'	1.399 (3)	C7'—H7'	0.9500
C7'—C8'	1.363 (2)	C8'—H8'	0.9500
C1—O2—C3	109.55 (14)	C9'—C1'—H1'	119.00
C1—O6—C5	110.36 (13)	O2—C3—H3A	110.00
O2—C1—O6	110.99 (13)	O2—C3—H3E	110.00
O2—C1—C2'	108.32 (13)	C4—C3—H3A	110.00
O6—C1—C2'	108.84 (13)	C4—C3—H3E	110.00
C2'—C1'—C9'	121.09 (14)	H3A—C3—H3E	108.00
C1—C2'—C1'	120.15 (14)	C2'—C3'—H3'	120.00
C1—C2'—C3'	119.63 (14)	C4'—C3'—H3'	120.00
C1'—C2'—C3'	120.22 (15)	C3—C4—H4A	110.00
O2—C3—C4	110.27 (15)	C3—C4—H4E	110.00
C2'—C3'—C4'	119.98 (19)	C5—C4—H4A	110.00
C3—C4—C5	109.96 (18)	C5—C4—H4E	110.00
C3'—C4'—C10'	121.12 (17)	H4A—C4—H4E	108.00
O6—C5—C4	110.33 (18)	C3'—C4'—H4'	119.00
C6'—C5'—C10'	120.74 (16)	C10'—C4'—H4'	119.00
C5'—C6'—C7'	120.65 (17)	O6—C5—H5A	110.00
C6'—C7'—C8'	120.42 (19)	O6—C5—H5E	110.00
C7'—C8'—C9'	120.64 (16)	C4—C5—H5A	110.00
C1'—C9'—C8'	122.48 (14)	C4—C5—H5E	110.00
C1'—C9'—C10'	118.47 (14)	H5A—C5—H5E	108.00
C8'—C9'—C10'	119.06 (14)	C6'—C5'—H5'	120.00
C4'—C10'—C5'	122.42 (15)	C10'—C5'—H5'	120.00
C4'—C10'—C9'	119.09 (14)	C5'—C6'—H6'	120.00
C5'—C10'—C9'	118.49 (15)	C7'—C6'—H6'	120.00
O2—C1—H1	110.00	C6'—C7'—H7'	120.00
O6—C1—H1	110.00	C8'—C7'—H7'	120.00
C2'—C1—H1	110.00	C7'—C8'—H8'	120.00
C2'—C1'—H1'	119.00	C9'—C8'—H8'	120.00
C3—O2—C1—O6	64.83 (17)	O2—C3—C4—C5	51.9 (2)
C3—O2—C1—C2'	−175.74 (14)	C2'—C3'—C4'—C10'	−0.1 (3)
C1—O2—C3—C4	−58.4 (2)	C3—C4—C5—O6	−50.8 (2)
C5—O6—C1—O2	−64.14 (17)	C3'—C4'—C10'—C5'	179.07 (16)
C5—O6—C1—C2'	176.74 (14)	C3'—C4'—C10'—C9'	−1.3 (2)
C1—O6—C5—C4	56.5 (2)	C10'—C5'—C6'—C7'	−0.6 (3)
O2—C1—C2'—C1'	104.47 (17)	C6'—C5'—C10'—C4'	179.42 (16)
O2—C1—C2'—C3'	−75.40 (18)	C6'—C5'—C10'—C9'	−0.2 (2)
O6—C1—C2'—C1'	−134.75 (15)	C5'—C6'—C7'—C8'	0.4 (3)
O6—C1—C2'—C3'	45.38 (19)	C6'—C7'—C8'—C9'	0.6 (2)
C9'—C1'—C2'—C1	179.19 (14)	C7'—C8'—C9'—C1'	178.60 (15)
C9'—C1'—C2'—C3'	−0.9 (2)	C7'—C8'—C9'—C10'	−1.4 (2)
C2'—C1'—C9'—C8'	179.59 (15)	C1'—C9'—C10'—C4'	1.6 (2)
C2'—C1'—C9'—C10'	−0.5 (2)	C1'—C9'—C10'—C5'	−178.80 (14)
C1—C2'—C3'—C4'	−178.90 (15)	C8'—C9'—C10'—C4'	−178.48 (15)
C1'—C2'—C3'—C4'	1.2 (2)	C8'—C9'—C10'—C5'	1.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1'—H1'···O2i	0.95	2.60	3.349 (2)	136
C5'—H5'···Cg1ii	0.95	2.70	3.555 (2)	151
C4'—H4'···Cg2ii	0.95	2.92	3.776 (2)	150
C3—H3A···Cg1i	0.99	2.99	3.927 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1′–C4′/C9′/C10′ and C5′–C10′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1′—H1′⋯O2i	0.95	2.60	3.349 (2)	136
C5′—H5′⋯Cg1ii	0.95	2.70	3.555 (2)	151
C4′—H4′⋯Cg2ii	0.95	2.92	3.776 (2)	150
C3—H3A⋯Cg1i	0.99	2.99	3.927 (2)	159

Symmetry codes: (i) ; (ii) .