2-(2-Naphth­yl)-1,3-dioxane

Thevenet, D.; Neier, R.; Stoeckli-Evans, H.

doi:10.1107/S1600536810000644

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages o473-o474

https://doi.org/10.1107/S1600536810000644

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2-(2-Naphthyl)-1,3-dioxane

Damien Thevenet,^a Reinhard Neier ^a ^* and Helen Stoeckli-Evans ^b

^aInstitute of Chemistry, University of Neuchâtel, rue Emile-Argand 11, 2009 Neuchâtel, Switzerland, and ^bInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, 2009 Neuchâtel, Switzerland
^*Correspondence e-mail: rienhard.neier@unine.ch

(Received 30 December 2009; accepted 6 January 2010; online 30 January 2010)

The title compound, C₁₄H₁₄O₂, crystallizes in the chiral monoclinic space group P2₁. 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 molecules are connected via a weak C—H⋯O interaction to form a helical chain propagating in [010]. While there are no π–π stacking interactions present, there are weak C—H⋯π interactions 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_r = 214.25
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.024
wR(F²) = 0.061
S = 1.05
1098 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.11 e Å⁻³

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) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+2]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000644/cv2685Isup2.hkl

checkCIF report

Comment top

Acetals are the most commonly used protecting groups for carbonyl compounds in organic synthesis (Kocienski, 1994; Showler & Darley, 1967), and many methods have been developed for their deprotection (Cordes & Bull, 1974; Fujioka et al., 2004; Ates et al., 2003). The title 2-naphthaldehyde acetal (Newman & Dickson, 1970; Carmichael & Hug, 1986) was synthesized to investigate the scope of a new photochemical reaction capable of hydrolysing the acetal into an aldehyde (Thevenet & Neier, 2010). The NMR spectra of the unsubstituted 1,3-dioxane ring displays a complicated AA'BB'MN system (Buys & Eliel, 1970), and the X-ray crystal structure was helpful for the interpretation of the NMR spectra (Thevenet & Neier, 2010).

The structure of the title compound is illustrated in Fig. 1, and the geometrical parameters are given in the Supplementary information and the archived CIF. The bond lengths and angles are close to those in three similar compounds located in the Cambridge Crystal Structure Database (CSD, V 5.30, last update Sept. 2009; Allen, 2002). For example, methyl 2,3-di-O-acteyl-4,6-O-(2-naphthyl)methylene-α-D-galactopyranoside (Borbas et al., 2002), which also crystallized in the monoclinic space group P2₁, and where the naphthalene ring is planar and the two six-membered rings in the galactopyranoside unit have chair conformations.

In the crystal of the title compound symmetry related molecules are connected via a C—H···O interaction (Table 1) giving rise to the formation of helical chains propagating in [010]. These chains are further linked via weak C—H···π interactions to form a two-dimensional network in (011) - see Fig. 2 and Table 1 for details.

Related literature top

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 top

The title compound was synthesized using a modified strategy described by (Gopinath et al., 2002). To a solution of 2-naphthaldehyde (0.64 mmol), trimethylorthoformate (1.41 mmol) and 1,3-propanediol (5.12 mmol) in dry nitromethane (2 ml) was added tetrabutylammonium tribromide (0.025 mmol). The homogeneous reaction mixture was stirred at r.t. and the progress of the reaction monitored by TLC and GC. After completion of the reaction the mixture was poured into a solution of NaHCO₃ (10 ml) and the products were extracted with diethyl ether (3 × 10 ml). The organic layer was separated, dried over anhydrous Na₂SO₄ and concentrated. The white solid obtained was purified by recrystallization in MeOH, giving colourless thin plate-like crystals of the title compound.

¹H NMR 400 MHz (CDCl₃) δ 7.97 (br s, 1H, H_1'), 7.85 (m, 3H, H_4',5',8'), 7.60 (dd, 1H, ³J_3'-4' = 8.5 Hz, ³J_3'-1' = 1.7 Hz, H_3'), 7.48 (m, 2H, H_6',7'), 5.68 (s, 1H, H₁), 4.33 (dddd, 2H, ²J_3e-3a;5e-5a = -11.7 Hz, ³J_3e-4a;5e-4a = 5.0 Hz, ³J_3e-4e;5e-4e = 1.5 Hz, ⁴J_3e-5e = 3.0 Hz, H_3e,5e), 4.06 (ddd, 2H, ²J_3a-3e;5a-5e = -11.7 Hz, ³J_3a-4a;5a-4a = 12.4 Hz, ³J_3a-4e;5a-4e = 2.7 Hz, H_3a,5a), 2.29( dtt, 1H, ²J_4a-4e = -13.5 Hz, ³J_4a-3a;4a-5a = 12.4 Hz, ³J_4a-3e;4a-5e = 5.0 Hz, H_4a), 1.50 (dtt, 1H, ²J_4e-4a = -13.5 Hz, ³J_4e-3a;4e-5a = 2.7 Hz, ³J_4e-3e;4e-5e = 1.5 Hz, H_{4 e}); ¹³C NMR 100 MHz (CDCl₃) δ 136.1 (C_2'), (133.6, 133.1) (C_9',10'), (128.4, 128.1, 127.7) (C_4',5',8'), (126.2, 126.0) (C_6',7'), 125.3 (C_1'), 123.8 (C_3'), 101.8 (C₁), 67.5 (C_3,5), 25.9 (C₄); HRMS (ESI, +): [M + Na]⁺ = 237.09. Note: The same numbering scheme has been used for the crystal structure (Fig. 1). The torsional angles of the 1,3-dioxane ring were measured to estimate the coupling constants according to the Karplus equation.

Structure description top

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).

Computing details top

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell refinement: CELL in IPDS-I (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDS-I (Stoe & Cie, 2000); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. A view of the molecular structure of the title compound, with displacement ellipoids drawn at the 50% probabilty level.

Fig. 2. A view along the a axis of the crystal packing of the title compound. The C—H···O and C—H···π interactions are shown as dotted cyan and black lines, respectively. [The blue balls represent the centroids of the two aromatic rings; H-atoms not involved in the C—H···O and C—H···π interactions have been omitted for clarity; the C—H···π interactions are shown for one molecule only; see Table 1 for details].

2-(2-Naphthyl)-1,3-dioxane top

Crystal data top

C₁₄H₁₄O₂	F(000) = 228
M_r = 214.25	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0412P)²] where P = (F_o² + 2F_c²)/3
1098 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₄H₁₄O₂	V = 556.20 (9) Å³
M_r = 214.25	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.5351 (6) Å	µ = 0.08 mm⁻¹
b = 7.8575 (8) Å	T = 173 K
c = 9.4057 (9) Å	0.38 × 0.30 × 0.08 mm
β = 92.839 (11)°

Data collection top

Stoe IPDS diffractometer	951 reflections with I > 2σ(I)
4461 measured reflections	R_int = 0.024
1098 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	1 restraint
wR(F²) = 0.061	H-atom parameters constrained
S = 1.05	Δρ_max = 0.13 e Å⁻³
1098 reflections	Δρ_min = −0.11 e Å⁻³
145 parameters

Special details top

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 U_iso(H) = 1.2U_eq(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄O₂
M_r	214.25
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.5351 (6), 7.8575 (8), 9.4057 (9)
β (°)	92.839 (11)
V (Å³)	556.20 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.38 × 0.30 × 0.08

Data collection
Diffractometer	Stoe IPDS
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4461, 1098, 951
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.061, 1.05
No. of reflections	1098
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.11

Computer programs: EXPOSE in IPDS-I (Stoe & Cie, 2000), CELL in IPDS-I (Stoe & Cie, 2000), INTEGRATE in IPDS-I (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+2.

Acknowledgements

HSE is grateful to the XRD Application Laboratory, Microsystems Technology Division, Swiss Center for Electronics and Microtechnology, Neuchâtel, for access to the X-ray diffraction equipment.

References

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