(5-n-Heptyl-2-hydroxymethyl-1,3-dioxan-2-yl)methanol

Yuan, X.-Y.; Zhang, M.; Ng, S.W.

doi:10.1107/S1600536810041413

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2918

https://doi.org/10.1107/S1600536810041413

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(5-n-Heptyl-2-hydroxymethyl-1,3-dioxan-2-yl)methanol

Xian-You Yuan,^a Min Zhang ^a and Seik Weng Ng ^b ^*

^aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou Hunan 425100, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 13 October 2010; accepted 14 October 2010; online 23 October 2010)

In the title compound, C₁₃H₂₆O₄, the dioxane rings adopts a chair conformation; the n-heptyl chain occupies an equatorial position. In the crystal, molecules are connected by O—H⋯O hydrogen bonds into a zigzag chain running along the a axis, giving rise to a herringbone pattern. There are two independent molecules in the asymmetric unit.

Related literature

For a related structure, see: Luo et al. (2008 ).

Experimental

Crystal data

C₁₃H₂₆O₄
M_r = 246.34
Monoclinic, P 2₁ /n
a = 5.8030 (4) Å
b = 54.017 (4) Å
c = 9.1018 (6) Å
β = 92.938 (1)°
V = 2849.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 163 K
0.40 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
14414 measured reflections
6156 independent reflections
3242 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.201
S = 1.05
6156 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O7	0.84	1.94	2.736 (3)	159
O4—H4⋯O3ⁱ	0.84	1.82	2.656 (3)	171
O7—H7⋯O8ⁱⁱ	0.84	1.82	2.646 (3)	167
O8—H8⋯O4	0.84	1.92	2.701 (3)	155
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041413/bt5378sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041413/bt5378Isup2.hkl

checkCIF report

Comment top

A previous study reported the crystal structure of 5,5-bis(hydroxylmethyl)-2-phenylmethyl-1,3-dioxane, which was synthesized by the condensation of 2,2-bis(hydroxymethyl)-1,3-propanediol and an aromatic aldehyde (benzaldehyde) (Luo et al., 2008). A variation of the synthesis with an aliphatic aldehyde under similar reaction conditions yielded a 1,3-dixoxane having the hydroxyl groups connected to another atom of the chair-shaped ring. In the molecule of the C₁₃H₂₆O₄ (Scheme I, Fig. 1), the n-heptyl chain occupies an equatorial position. The molecules are connected by O–H···O hydrogen-bonds to a zigzag chain running along the a-axis of the monoclinic unit cell giving rise to a herring-bone pattern. (Fig. 2).

Related literature top

For a related structure, see: Luo et al. (2008).

Experimental top

2,2-Bis(hydroxymethyl)-1,3-propanediol (13.0 g, 96 mmol) and N,N-dimethylformamide (100 ml) were heated until the 2,2-bis(hydroxymethyl)-1,3-propanediol dissolved completely. n-Octanal (11.4 g, 89 mmol) and p-toluenesulfonic acid monohydrate (1 g, 5 mmol) were added. The solution was heated 363–373 K 5 h. The solution was cooled and ethyl acetate (100 ml) was added to dissolve the residue after DMF was removed by evaporation. The solution was washed successively with water and 5% sodium bicarbonate (50 ml); the solution was dried over sodium sulfate. The solvent was evaporated to give a solid that was recrystallized from ethyl acetate to yield 16.0 g (65%) of colorless crystals.

Structure description top

For a related structure, see: Luo et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₃H₂₆O₄ at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Partial packing diagram of the title compound showing the hydrogen-bonds as dashed lines.

(5-n-Heptyl-2-hydroxymethyl-1,3-dioxan-2-yl)methanol top

Crystal data top

C₁₃H₂₆O₄	F(000) = 1088
M_r = 246.34	D_x = 1.149 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2633 reflections
a = 5.8030 (4) Å	θ = 2.4–26.3°
b = 54.017 (4) Å	µ = 0.08 mm⁻¹
c = 9.1018 (6) Å	T = 163 K
β = 92.938 (1)°	Prism, colorless
V = 2849.3 (3) Å³	0.40 × 0.35 × 0.15 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	3242 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.077
Graphite monochromator	θ_max = 27.1°, θ_min = 2.3°
ω scans	h = −6→7
14414 measured reflections	k = −58→69
6156 independent reflections	l = −10→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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0842P)²] where P = (F_o² + 2F_c²)/3
6156 reflections	(Δ/σ)_max = 0.001
311 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₃H₂₆O₄	V = 2849.3 (3) Å³
M_r = 246.34	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8030 (4) Å	µ = 0.08 mm⁻¹
b = 54.017 (4) Å	T = 163 K
c = 9.1018 (6) Å	0.40 × 0.35 × 0.15 mm
β = 92.938 (1)°

Data collection top

Bruker SMART APEX diffractometer	3242 reflections with I > 2σ(I)
14414 measured reflections	R_int = 0.077
6156 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
6156 reflections	Δρ_min = −0.32 e Å⁻³
311 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.2272 (3)	0.13631 (4)	0.3678 (2)	0.0193 (5)
O2	−0.0529 (4)	0.13323 (4)	0.1752 (2)	0.0230 (5)
O3	−0.4134 (3)	0.19510 (4)	0.3742 (3)	0.0243 (6)
H3	−0.3489	0.2088	0.3615	0.036*
O4	0.1374 (4)	0.20487 (4)	0.3614 (3)	0.0281 (6)
H4	0.2795	0.2022	0.3747	0.042*
O5	0.1796 (4)	0.31378 (4)	0.4361 (2)	0.0247 (5)
O6	−0.1028 (3)	0.32156 (4)	0.2493 (2)	0.0202 (5)
O7	−0.3125 (4)	0.24297 (4)	0.3030 (3)	0.0254 (6)
H7	−0.4518	0.2468	0.2868	0.038*
O8	0.2389 (4)	0.25210 (4)	0.2915 (3)	0.0261 (6)
H8	0.1682	0.2387	0.3026	0.039*
C1	0.0843 (5)	0.15190 (5)	0.4533 (3)	0.0167 (7)
H1A	0.1831	0.1635	0.5124	0.020*
H1B	−0.0009	0.1415	0.5220	0.020*
C2	−0.0868 (5)	0.16654 (5)	0.3557 (3)	0.0157 (7)
C3	−0.2132 (5)	0.14847 (5)	0.2508 (4)	0.0212 (7)
H3A	−0.3156	0.1378	0.3070	0.025*
H3B	−0.3107	0.1579	0.1778	0.025*
C4	0.0368 (5)	0.18620 (6)	0.2664 (4)	0.0224 (7)
H4A	0.1590	0.1782	0.2110	0.027*
H4B	−0.0750	0.1940	0.1946	0.027*
C5	−0.2576 (5)	0.17895 (6)	0.4544 (4)	0.0208 (7)
H5A	−0.3471	0.1660	0.5035	0.025*
H5B	−0.1711	0.1885	0.5318	0.025*
C6	0.0909 (5)	0.12001 (5)	0.2773 (3)	0.0184 (7)
H6A	−0.0054	0.1094	0.3399	0.022*
C7	0.2514 (6)	0.10397 (6)	0.1932 (4)	0.0243 (8)
H7A	0.3531	0.1147	0.1369	0.029*
H7B	0.1589	0.0937	0.1218	0.029*
C8	0.4005 (5)	0.08698 (6)	0.2924 (4)	0.0231 (8)
H8A	0.4899	0.0972	0.3655	0.028*
H8B	0.2988	0.0759	0.3469	0.028*
C9	0.5668 (6)	0.07125 (6)	0.2086 (4)	0.0270 (8)
H9A	0.6675	0.0823	0.1534	0.032*
H9B	0.4774	0.0609	0.1363	0.032*
C10	0.7177 (6)	0.05444 (6)	0.3086 (4)	0.0278 (8)
H10A	0.8078	0.0648	0.3803	0.033*
H10B	0.6166	0.0436	0.3647	0.033*
C11	0.8834 (6)	0.03837 (6)	0.2267 (4)	0.0312 (9)
H11A	0.7934	0.0278	0.1561	0.037*
H11B	0.9834	0.0492	0.1695	0.037*
C12	1.0346 (6)	0.02205 (7)	0.3272 (5)	0.0397 (10)
H12A	0.9345	0.0113	0.3851	0.048*
H12B	1.1254	0.0327	0.3973	0.048*
C13	1.1999 (7)	0.00570 (7)	0.2452 (5)	0.0547 (13)
H13A	1.2931	−0.0042	0.3161	0.082*
H13B	1.3015	0.0161	0.1888	0.082*
H13C	1.1113	−0.0053	0.1781	0.082*
C14	0.0664 (6)	0.29187 (6)	0.4811 (4)	0.0220 (7)
H14A	−0.0366	0.2960	0.5610	0.026*
H14B	0.1830	0.2799	0.5203	0.026*
C15	−0.0747 (5)	0.28004 (5)	0.3539 (3)	0.0169 (7)
C16	−0.2343 (5)	0.30020 (5)	0.2872 (4)	0.0211 (7)
H16A	−0.3186	0.2937	0.1981	0.025*
H16B	−0.3491	0.3049	0.3589	0.025*
C17	−0.2122 (5)	0.25857 (5)	0.4161 (3)	0.0197 (7)
H17A	−0.1088	0.2486	0.4824	0.024*
H17B	−0.3363	0.2653	0.4752	0.024*
C18	0.0813 (5)	0.27046 (5)	0.2361 (4)	0.0198 (7)
H18A	−0.0156	0.2634	0.1538	0.024*
H18B	0.1691	0.2845	0.1969	0.024*
C19	0.0221 (5)	0.33143 (5)	0.3746 (4)	0.0208 (7)
H19A	−0.0880	0.3365	0.4500	0.025*
C20	0.1590 (6)	0.35353 (5)	0.3288 (4)	0.0241 (8)
H20A	0.2648	0.3482	0.2529	0.029*
H20B	0.2550	0.3594	0.4149	0.029*
C21	0.0146 (6)	0.37513 (6)	0.2682 (4)	0.0258 (8)
H21A	−0.0694	0.3826	0.3492	0.031*
H21B	−0.1016	0.3688	0.1942	0.031*
C22	0.1565 (6)	0.39521 (6)	0.1974 (4)	0.0243 (8)
H22A	0.2339	0.3878	0.1134	0.029*
H22B	0.0499	0.4082	0.1576	0.029*
C23	0.3386 (6)	0.40747 (6)	0.2992 (4)	0.0276 (8)
H23A	0.4417	0.3945	0.3427	0.033*
H23B	0.2613	0.4156	0.3806	0.033*
C24	0.4845 (6)	0.42659 (6)	0.2228 (4)	0.0292 (8)
H24A	0.5621	0.4184	0.1414	0.035*
H24B	0.3816	0.4396	0.1793	0.035*
C25	0.6657 (6)	0.43875 (6)	0.3251 (4)	0.0333 (9)
H25A	0.7675	0.4257	0.3690	0.040*
H25B	0.5875	0.4469	0.4061	0.040*
C26	0.8145 (7)	0.45783 (7)	0.2509 (5)	0.0425 (10)
H26A	0.9262	0.4649	0.3237	0.064*
H26B	0.7160	0.4711	0.2089	0.064*
H26C	0.8969	0.4498	0.1724	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0133 (11)	0.0229 (11)	0.0217 (12)	0.0027 (9)	0.0007 (9)	−0.0051 (10)
O2	0.0214 (12)	0.0264 (12)	0.0208 (13)	0.0071 (10)	−0.0022 (9)	−0.0041 (10)
O3	0.0139 (11)	0.0199 (12)	0.0389 (15)	0.0018 (9)	0.0005 (10)	0.0019 (11)
O4	0.0125 (12)	0.0232 (12)	0.0488 (16)	−0.0011 (10)	0.0019 (11)	−0.0060 (11)
O5	0.0221 (12)	0.0233 (12)	0.0279 (14)	−0.0045 (10)	−0.0058 (10)	0.0055 (10)
O6	0.0183 (11)	0.0230 (11)	0.0190 (12)	−0.0029 (9)	−0.0038 (9)	−0.0013 (10)
O7	0.0126 (11)	0.0272 (12)	0.0363 (15)	−0.0046 (10)	0.0006 (10)	−0.0030 (11)
O8	0.0164 (12)	0.0223 (12)	0.0397 (15)	0.0025 (9)	0.0032 (10)	0.0043 (11)
C1	0.0169 (16)	0.0177 (16)	0.0155 (17)	0.0027 (13)	0.0005 (12)	−0.0030 (13)
C2	0.0099 (15)	0.0187 (16)	0.0185 (17)	0.0020 (12)	0.0000 (12)	−0.0003 (13)
C3	0.0155 (16)	0.0214 (16)	0.0268 (19)	0.0025 (13)	0.0017 (13)	−0.0042 (14)
C4	0.0150 (16)	0.0236 (17)	0.029 (2)	−0.0029 (14)	0.0016 (14)	−0.0007 (15)
C5	0.0166 (17)	0.0214 (16)	0.0245 (19)	0.0038 (13)	0.0018 (13)	0.0008 (14)
C6	0.0182 (17)	0.0201 (16)	0.0167 (17)	0.0025 (13)	−0.0005 (13)	−0.0025 (14)
C7	0.0239 (18)	0.0271 (18)	0.0220 (19)	0.0021 (14)	0.0018 (14)	−0.0042 (15)
C8	0.0229 (18)	0.0214 (17)	0.025 (2)	0.0039 (14)	0.0027 (14)	−0.0019 (14)
C9	0.0276 (19)	0.0283 (18)	0.026 (2)	0.0039 (15)	0.0046 (15)	−0.0028 (15)
C10	0.0253 (19)	0.0220 (17)	0.036 (2)	0.0049 (15)	0.0012 (16)	−0.0001 (16)
C11	0.0252 (19)	0.0247 (18)	0.044 (2)	0.0045 (15)	0.0056 (17)	−0.0003 (17)
C12	0.028 (2)	0.030 (2)	0.061 (3)	0.0070 (16)	0.0023 (19)	0.0008 (19)
C13	0.036 (2)	0.042 (2)	0.087 (4)	0.015 (2)	0.015 (2)	0.003 (2)
C14	0.0246 (18)	0.0225 (17)	0.0186 (18)	−0.0003 (14)	−0.0010 (14)	0.0023 (14)
C15	0.0129 (15)	0.0190 (16)	0.0186 (17)	−0.0002 (13)	−0.0007 (12)	0.0028 (13)
C16	0.0145 (16)	0.0221 (17)	0.0268 (19)	−0.0019 (13)	0.0022 (13)	0.0014 (14)
C17	0.0157 (16)	0.0213 (16)	0.0225 (19)	−0.0008 (13)	0.0051 (13)	0.0022 (14)
C18	0.0130 (16)	0.0189 (16)	0.0276 (19)	0.0016 (13)	0.0030 (13)	0.0016 (14)
C19	0.0203 (17)	0.0203 (17)	0.0214 (18)	−0.0009 (13)	−0.0036 (13)	−0.0030 (14)
C20	0.0266 (18)	0.0213 (17)	0.0244 (19)	0.0001 (14)	−0.0003 (14)	0.0026 (14)
C21	0.0263 (19)	0.0203 (17)	0.031 (2)	−0.0016 (14)	0.0005 (15)	0.0009 (15)
C22	0.0296 (19)	0.0197 (17)	0.0236 (19)	−0.0011 (14)	0.0030 (15)	0.0017 (14)
C23	0.033 (2)	0.0254 (18)	0.025 (2)	−0.0035 (15)	0.0024 (15)	0.0036 (15)
C24	0.032 (2)	0.0276 (19)	0.028 (2)	0.0004 (16)	0.0066 (16)	0.0041 (16)
C25	0.032 (2)	0.0304 (19)	0.037 (2)	−0.0052 (16)	0.0015 (17)	0.0010 (17)
C26	0.040 (2)	0.034 (2)	0.054 (3)	−0.0042 (18)	0.009 (2)	0.0079 (19)

Geometric parameters (Å, º) top

O1—C6	1.418 (4)	C11—H11A	0.9900
O1—C1	1.438 (3)	C11—H11B	0.9900
O2—C6	1.411 (4)	C12—C13	1.527 (5)
O2—C3	1.443 (3)	C12—H12A	0.9900
O3—C5	1.430 (4)	C12—H12B	0.9900
O3—H3	0.8400	C13—H13A	0.9800
O4—C4	1.433 (4)	C13—H13B	0.9800
O4—H4	0.8400	C13—H13C	0.9800
O5—C19	1.417 (4)	C14—C15	1.524 (4)
O5—C14	1.423 (3)	C14—H14A	0.9900
O6—C19	1.423 (4)	C14—H14B	0.9900
O6—C16	1.435 (3)	C15—C18	1.529 (4)
O7—C17	1.431 (4)	C15—C17	1.533 (4)
O7—H7	0.8400	C15—C16	1.534 (4)
O8—C18	1.424 (4)	C16—H16A	0.9900
O8—H8	0.8400	C16—H16B	0.9900
C1—C2	1.520 (4)	C17—H17A	0.9900
C1—H1A	0.9900	C17—H17B	0.9900
C1—H1B	0.9900	C18—H18A	0.9900
C2—C3	1.526 (4)	C18—H18B	0.9900
C2—C5	1.527 (4)	C19—C20	1.505 (4)
C2—C4	1.537 (4)	C19—H19A	1.0000
C3—H3A	0.9900	C20—C21	1.523 (4)
C3—H3B	0.9900	C20—H20A	0.9900
C4—H4A	0.9900	C20—H20B	0.9900
C4—H4B	0.9900	C21—C22	1.525 (4)
C5—H5A	0.9900	C21—H21A	0.9900
C5—H5B	0.9900	C21—H21B	0.9900
C6—C7	1.509 (4)	C22—C23	1.521 (4)
C6—H6A	1.0000	C22—H22A	0.9900
C7—C8	1.525 (4)	C22—H22B	0.9900
C7—H7A	0.9900	C23—C24	1.526 (4)
C7—H7B	0.9900	C23—H23A	0.9900
C8—C9	1.520 (4)	C23—H23B	0.9900
C8—H8A	0.9900	C24—C25	1.518 (5)
C8—H8B	0.9900	C24—H24A	0.9900
C9—C10	1.529 (4)	C24—H24B	0.9900
C9—H9A	0.9900	C25—C26	1.524 (5)
C9—H9B	0.9900	C25—H25A	0.9900
C10—C11	1.519 (4)	C25—H25B	0.9900
C10—H10A	0.9900	C26—H26A	0.9800
C10—H10B	0.9900	C26—H26B	0.9800
C11—C12	1.517 (5)	C26—H26C	0.9800

C6—O1—C1	110.9 (2)	H13A—C13—H13B	109.5
C6—O2—C3	110.4 (2)	C12—C13—H13C	109.5
C5—O3—H3	109.5	H13A—C13—H13C	109.5
C4—O4—H4	109.5	H13B—C13—H13C	109.5
C19—O5—C14	112.0 (2)	O5—C14—C15	111.6 (2)
C19—O6—C16	111.3 (2)	O5—C14—H14A	109.3
C17—O7—H7	109.5	C15—C14—H14A	109.3
C18—O8—H8	109.5	O5—C14—H14B	109.3
O1—C1—C2	111.5 (2)	C15—C14—H14B	109.3
O1—C1—H1A	109.3	H14A—C14—H14B	108.0
C2—C1—H1A	109.3	C14—C15—C18	111.1 (2)
O1—C1—H1B	109.3	C14—C15—C17	107.8 (2)
C2—C1—H1B	109.3	C18—C15—C17	110.0 (2)
H1A—C1—H1B	108.0	C14—C15—C16	107.1 (2)
C1—C2—C3	108.1 (2)	C18—C15—C16	109.2 (3)
C1—C2—C5	108.0 (2)	C17—C15—C16	111.6 (2)
C3—C2—C5	110.1 (2)	O6—C16—C15	110.4 (2)
C1—C2—C4	111.1 (2)	O6—C16—H16A	109.6
C3—C2—C4	109.5 (2)	C15—C16—H16A	109.6
C5—C2—C4	110.0 (2)	O6—C16—H16B	109.6
O2—C3—C2	111.2 (2)	C15—C16—H16B	109.6
O2—C3—H3A	109.4	H16A—C16—H16B	108.1
C2—C3—H3A	109.4	O7—C17—C15	112.3 (2)
O2—C3—H3B	109.4	O7—C17—H17A	109.1
C2—C3—H3B	109.4	C15—C17—H17A	109.1
H3A—C3—H3B	108.0	O7—C17—H17B	109.1
O4—C4—C2	110.8 (3)	C15—C17—H17B	109.1
O4—C4—H4A	109.5	H17A—C17—H17B	107.9
C2—C4—H4A	109.5	O8—C18—C15	112.3 (3)
O4—C4—H4B	109.5	O8—C18—H18A	109.1
C2—C4—H4B	109.5	C15—C18—H18A	109.1
H4A—C4—H4B	108.1	O8—C18—H18B	109.1
O3—C5—C2	112.3 (3)	C15—C18—H18B	109.1
O3—C5—H5A	109.1	H18A—C18—H18B	107.9
C2—C5—H5A	109.1	O5—C19—O6	110.9 (2)
O3—C5—H5B	109.1	O5—C19—C20	107.7 (2)
C2—C5—H5B	109.1	O6—C19—C20	109.3 (3)
H5A—C5—H5B	107.9	O5—C19—H19A	109.6
O2—C6—O1	111.2 (2)	O6—C19—H19A	109.6
O2—C6—C7	108.4 (2)	C20—C19—H19A	109.6
O1—C6—C7	108.1 (2)	C19—C20—C21	114.8 (3)
O2—C6—H6A	109.7	C19—C20—H20A	108.6
O1—C6—H6A	109.7	C21—C20—H20A	108.6
C7—C6—H6A	109.7	C19—C20—H20B	108.6
C6—C7—C8	113.0 (3)	C21—C20—H20B	108.6
C6—C7—H7A	109.0	H20A—C20—H20B	107.5
C8—C7—H7A	109.0	C20—C21—C22	113.5 (3)
C6—C7—H7B	109.0	C20—C21—H21A	108.9
C8—C7—H7B	109.0	C22—C21—H21A	108.9
H7A—C7—H7B	107.8	C20—C21—H21B	108.9
C9—C8—C7	113.3 (3)	C22—C21—H21B	108.9
C9—C8—H8A	108.9	H21A—C21—H21B	107.7
C7—C8—H8A	108.9	C23—C22—C21	115.2 (3)
C9—C8—H8B	108.9	C23—C22—H22A	108.5
C7—C8—H8B	108.9	C21—C22—H22A	108.5
H8A—C8—H8B	107.7	C23—C22—H22B	108.5
C8—C9—C10	113.1 (3)	C21—C22—H22B	108.5
C8—C9—H9A	109.0	H22A—C22—H22B	107.5
C10—C9—H9B	109.0	C22—C23—C24	113.7 (3)
C8—C9—H9A	109.0	C22—C23—H23A	108.8
C10—C9—H9A	109.0	C24—C23—H23A	108.8
H9A—C9—H9B	107.8	C22—C23—H23B	108.8
C11—C10—C9	113.9 (3)	C24—C23—H23B	108.8
C11—C10—H10A	108.8	H23A—C23—H23B	107.7
C9—C10—H10A	108.8	C25—C24—C23	113.4 (3)
C11—C10—H10B	108.8	C25—C24—H24A	108.9
C9—C10—H10B	108.8	C23—C24—H24A	108.9
H10A—C10—H10B	107.7	C25—C24—H24B	108.9
C12—C11—C10	113.4 (3)	C23—C24—H24B	108.9
C12—C11—H11A	108.9	H24A—C24—H24B	107.7
C10—C11—H11A	108.9	C24—C25—C26	114.3 (3)
C12—C11—H11B	108.9	C24—C25—H25A	108.7
C10—C11—H11B	108.9	C26—C25—H25A	108.7
H11A—C11—H11B	107.7	C24—C25—H25B	108.7
C11—C12—C13	113.6 (3)	C26—C25—H25B	108.7
C11—C12—H12A	108.9	H25A—C25—H25B	107.6
C13—C12—H12A	108.9	C25—C26—H26A	109.5
C11—C12—H12B	108.9	C25—C26—H26B	109.5
C13—C12—H12B	108.9	H26A—C26—H26B	109.5
H12A—C12—H12B	107.7	C25—C26—H26C	109.5
C12—C13—H13A	109.5	H26A—C26—H26C	109.5
C12—C13—H13B	109.5	H26B—C26—H26C	109.5

C6—O1—C1—C2	−56.8 (3)	C19—O5—C14—C15	57.2 (3)
O1—C1—C2—C3	51.2 (3)	O5—C14—C15—C18	66.1 (3)
O1—C1—C2—C5	170.2 (2)	O5—C14—C15—C17	−173.3 (2)
O1—C1—C2—C4	−69.0 (3)	O5—C14—C15—C16	−53.1 (3)
C6—O2—C3—C2	57.9 (3)	C19—O6—C16—C15	−59.0 (3)
C1—C2—C3—O2	−51.7 (3)	C14—C15—C16—O6	53.9 (3)
C5—C2—C3—O2	−169.5 (2)	C18—C15—C16—O6	−66.5 (3)
C4—C2—C3—O2	69.5 (3)	C17—C15—C16—O6	171.7 (2)
C1—C2—C4—O4	−66.5 (3)	C14—C15—C17—O7	−167.6 (2)
C3—C2—C4—O4	174.1 (2)	C18—C15—C17—O7	−46.3 (3)
C5—C2—C4—O4	53.0 (3)	C16—C15—C17—O7	75.1 (3)
C1—C2—C5—O3	174.5 (2)	C14—C15—C18—O8	60.5 (3)
C3—C2—C5—O3	−67.6 (3)	C17—C15—C18—O8	−58.8 (3)
C4—C2—C5—O3	53.1 (3)	C16—C15—C18—O8	178.4 (2)
C3—O2—C6—O1	−62.5 (3)	C14—O5—C19—O6	−59.6 (3)
C3—O2—C6—C7	178.8 (2)	C14—O5—C19—C20	−179.1 (2)
C1—O1—C6—O2	62.1 (3)	C16—O6—C19—O5	60.7 (3)
C1—O1—C6—C7	−179.0 (2)	C16—O6—C19—C20	179.3 (2)
O2—C6—C7—C8	−174.7 (2)	O5—C19—C20—C21	−176.5 (3)
O1—C6—C7—C8	64.6 (3)	O6—C19—C20—C21	62.9 (3)
C6—C7—C8—C9	−178.5 (3)	C19—C20—C21—C22	−169.5 (3)
C7—C8—C9—C10	179.4 (3)	C20—C21—C22—C23	−60.4 (4)
C8—C9—C10—C11	179.4 (3)	C21—C22—C23—C24	177.3 (3)
C9—C10—C11—C12	179.2 (3)	C22—C23—C24—C25	180.0 (3)
C10—C11—C12—C13	179.5 (3)	C23—C24—C25—C26	179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O7	0.84	1.94	2.736 (3)	159
O4—H4···O3ⁱ	0.84	1.82	2.656 (3)	171
O7—H7···O8ⁱⁱ	0.84	1.82	2.646 (3)	167
O8—H8···O4	0.84	1.92	2.701 (3)	155

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₆O₄
M_r	246.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	163
a, b, c (Å)	5.8030 (4), 54.017 (4), 9.1018 (6)
β (°)	92.938 (1)
V (Å³)	2849.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.35 × 0.15

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14414, 6156, 3242
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.201, 1.05
No. of reflections	6156
No. of parameters	311
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.32

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O7	0.84	1.94	2.736 (3)	159
O4—H4···O3ⁱ	0.84	1.82	2.656 (3)	171
O7—H7···O8ⁱⁱ	0.84	1.82	2.646 (3)	167
O8—H8···O4	0.84	1.92	2.701 (3)	155

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Acknowledgements

We thank the S&T Technology Planning Project of Hunan Province (No. 2010 N K3007), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023), the NSF of Hunan Province (09 J J3028), the Key Construction Project of Hunan Province (No. 2000–180) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2003). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Luo, Y.-M., Liu, X.-M., Yuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1536. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar