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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2918.
Published online 2010 October 23. doi:  10.1107/S1600536810041413
PMCID: PMC3009154

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

Abstract

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 [triangle]).

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Object name is e-66-o2918-scheme1.jpg

Experimental

Crystal data

  • C13H26O4
  • M r = 246.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2918-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.201
  • S = 1.05
  • 6156 reflections
  • 311 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.32 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041413/bt5378Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).

The hydroxy H-atoms were similarly placed (O–H 0.84%A) with Uiso(H) set to 1.5Ueq(O).

One of the axes of the unit cell is extremely long [54.017 (4) Å]; however, the crystal was sufficiently strongly diffracting at low temperature so that the refinement is stable, although it converged at a somewhat high R value.

Figures

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.

Crystal data

C13H26O4F(000) = 1088
Mr = 246.34Dx = 1.149 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2633 reflections
a = 5.8030 (4) Åθ = 2.4–26.3°
b = 54.017 (4) ŵ = 0.08 mm1
c = 9.1018 (6) ÅT = 163 K
β = 92.938 (1)°Prism, colorless
V = 2849.3 (3) Å30.40 × 0.35 × 0.15 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer3242 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
graphiteθmax = 27.1°, θmin = 2.3°
ω scansh = −6→7
14414 measured reflectionsk = −58→69
6156 independent reflectionsl = −10→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
6156 reflections(Δ/σ)max = 0.001
311 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.32 e Å3

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

xyzUiso*/Ueq
O10.2272 (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)
H3−0.34890.20880.36150.036*
O40.1374 (4)0.20487 (4)0.3614 (3)0.0281 (6)
H40.27950.20220.37470.042*
O50.1796 (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)
H7−0.45180.24680.28680.038*
O80.2389 (4)0.25210 (4)0.2915 (3)0.0261 (6)
H80.16820.23870.30260.039*
C10.0843 (5)0.15190 (5)0.4533 (3)0.0167 (7)
H1A0.18310.16350.51240.020*
H1B−0.00090.14150.52200.020*
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−0.31560.13780.30700.025*
H3B−0.31070.15790.17780.025*
C40.0368 (5)0.18620 (6)0.2664 (4)0.0224 (7)
H4A0.15900.17820.21100.027*
H4B−0.07500.19400.19460.027*
C5−0.2576 (5)0.17895 (6)0.4544 (4)0.0208 (7)
H5A−0.34710.16600.50350.025*
H5B−0.17110.18850.53180.025*
C60.0909 (5)0.12001 (5)0.2773 (3)0.0184 (7)
H6A−0.00540.10940.33990.022*
C70.2514 (6)0.10397 (6)0.1932 (4)0.0243 (8)
H7A0.35310.11470.13690.029*
H7B0.15890.09370.12180.029*
C80.4005 (5)0.08698 (6)0.2924 (4)0.0231 (8)
H8A0.48990.09720.36550.028*
H8B0.29880.07590.34690.028*
C90.5668 (6)0.07125 (6)0.2086 (4)0.0270 (8)
H9A0.66750.08230.15340.032*
H9B0.47740.06090.13630.032*
C100.7177 (6)0.05444 (6)0.3086 (4)0.0278 (8)
H10A0.80780.06480.38030.033*
H10B0.61660.04360.36470.033*
C110.8834 (6)0.03837 (6)0.2267 (4)0.0312 (9)
H11A0.79340.02780.15610.037*
H11B0.98340.04920.16950.037*
C121.0346 (6)0.02205 (7)0.3272 (5)0.0397 (10)
H12A0.93450.01130.38510.048*
H12B1.12540.03270.39730.048*
C131.1999 (7)0.00570 (7)0.2452 (5)0.0547 (13)
H13A1.2931−0.00420.31610.082*
H13B1.30150.01610.18880.082*
H13C1.1113−0.00530.17810.082*
C140.0664 (6)0.29187 (6)0.4811 (4)0.0220 (7)
H14A−0.03660.29600.56100.026*
H14B0.18300.27990.52030.026*
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−0.31860.29370.19810.025*
H16B−0.34910.30490.35890.025*
C17−0.2122 (5)0.25857 (5)0.4161 (3)0.0197 (7)
H17A−0.10880.24860.48240.024*
H17B−0.33630.26530.47520.024*
C180.0813 (5)0.27046 (5)0.2361 (4)0.0198 (7)
H18A−0.01560.26340.15380.024*
H18B0.16910.28450.19690.024*
C190.0221 (5)0.33143 (5)0.3746 (4)0.0208 (7)
H19A−0.08800.33650.45000.025*
C200.1590 (6)0.35353 (5)0.3288 (4)0.0241 (8)
H20A0.26480.34820.25290.029*
H20B0.25500.35940.41490.029*
C210.0146 (6)0.37513 (6)0.2682 (4)0.0258 (8)
H21A−0.06940.38260.34920.031*
H21B−0.10160.36880.19420.031*
C220.1565 (6)0.39521 (6)0.1974 (4)0.0243 (8)
H22A0.23390.38780.11340.029*
H22B0.04990.40820.15760.029*
C230.3386 (6)0.40747 (6)0.2992 (4)0.0276 (8)
H23A0.44170.39450.34270.033*
H23B0.26130.41560.38060.033*
C240.4845 (6)0.42659 (6)0.2228 (4)0.0292 (8)
H24A0.56210.41840.14140.035*
H24B0.38160.43960.17930.035*
C250.6657 (6)0.43875 (6)0.3251 (4)0.0333 (9)
H25A0.76750.42570.36900.040*
H25B0.58750.44690.40610.040*
C260.8145 (7)0.45783 (7)0.2509 (5)0.0425 (10)
H26A0.92620.46490.32370.064*
H26B0.71600.47110.20890.064*
H26C0.89690.44980.17240.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0133 (11)0.0229 (11)0.0217 (12)0.0027 (9)0.0007 (9)−0.0051 (10)
O20.0214 (12)0.0264 (12)0.0208 (13)0.0071 (10)−0.0022 (9)−0.0041 (10)
O30.0139 (11)0.0199 (12)0.0389 (15)0.0018 (9)0.0005 (10)0.0019 (11)
O40.0125 (12)0.0232 (12)0.0488 (16)−0.0011 (10)0.0019 (11)−0.0060 (11)
O50.0221 (12)0.0233 (12)0.0279 (14)−0.0045 (10)−0.0058 (10)0.0055 (10)
O60.0183 (11)0.0230 (11)0.0190 (12)−0.0029 (9)−0.0038 (9)−0.0013 (10)
O70.0126 (11)0.0272 (12)0.0363 (15)−0.0046 (10)0.0006 (10)−0.0030 (11)
O80.0164 (12)0.0223 (12)0.0397 (15)0.0025 (9)0.0032 (10)0.0043 (11)
C10.0169 (16)0.0177 (16)0.0155 (17)0.0027 (13)0.0005 (12)−0.0030 (13)
C20.0099 (15)0.0187 (16)0.0185 (17)0.0020 (12)0.0000 (12)−0.0003 (13)
C30.0155 (16)0.0214 (16)0.0268 (19)0.0025 (13)0.0017 (13)−0.0042 (14)
C40.0150 (16)0.0236 (17)0.029 (2)−0.0029 (14)0.0016 (14)−0.0007 (15)
C50.0166 (17)0.0214 (16)0.0245 (19)0.0038 (13)0.0018 (13)0.0008 (14)
C60.0182 (17)0.0201 (16)0.0167 (17)0.0025 (13)−0.0005 (13)−0.0025 (14)
C70.0239 (18)0.0271 (18)0.0220 (19)0.0021 (14)0.0018 (14)−0.0042 (15)
C80.0229 (18)0.0214 (17)0.025 (2)0.0039 (14)0.0027 (14)−0.0019 (14)
C90.0276 (19)0.0283 (18)0.026 (2)0.0039 (15)0.0046 (15)−0.0028 (15)
C100.0253 (19)0.0220 (17)0.036 (2)0.0049 (15)0.0012 (16)−0.0001 (16)
C110.0252 (19)0.0247 (18)0.044 (2)0.0045 (15)0.0056 (17)−0.0003 (17)
C120.028 (2)0.030 (2)0.061 (3)0.0070 (16)0.0023 (19)0.0008 (19)
C130.036 (2)0.042 (2)0.087 (4)0.015 (2)0.015 (2)0.003 (2)
C140.0246 (18)0.0225 (17)0.0186 (18)−0.0003 (14)−0.0010 (14)0.0023 (14)
C150.0129 (15)0.0190 (16)0.0186 (17)−0.0002 (13)−0.0007 (12)0.0028 (13)
C160.0145 (16)0.0221 (17)0.0268 (19)−0.0019 (13)0.0022 (13)0.0014 (14)
C170.0157 (16)0.0213 (16)0.0225 (19)−0.0008 (13)0.0051 (13)0.0022 (14)
C180.0130 (16)0.0189 (16)0.0276 (19)0.0016 (13)0.0030 (13)0.0016 (14)
C190.0203 (17)0.0203 (17)0.0214 (18)−0.0009 (13)−0.0036 (13)−0.0030 (14)
C200.0266 (18)0.0213 (17)0.0244 (19)0.0001 (14)−0.0003 (14)0.0026 (14)
C210.0263 (19)0.0203 (17)0.031 (2)−0.0016 (14)0.0005 (15)0.0009 (15)
C220.0296 (19)0.0197 (17)0.0236 (19)−0.0011 (14)0.0030 (15)0.0017 (14)
C230.033 (2)0.0254 (18)0.025 (2)−0.0035 (15)0.0024 (15)0.0036 (15)
C240.032 (2)0.0276 (19)0.028 (2)0.0004 (16)0.0066 (16)0.0041 (16)
C250.032 (2)0.0304 (19)0.037 (2)−0.0052 (16)0.0015 (17)0.0010 (17)
C260.040 (2)0.034 (2)0.054 (3)−0.0042 (18)0.009 (2)0.0079 (19)

Geometric parameters (Å, °)

O1—C61.418 (4)C11—H11A0.9900
O1—C11.438 (3)C11—H11B0.9900
O2—C61.411 (4)C12—C131.527 (5)
O2—C31.443 (3)C12—H12A0.9900
O3—C51.430 (4)C12—H12B0.9900
O3—H30.8400C13—H13A0.9800
O4—C41.433 (4)C13—H13B0.9800
O4—H40.8400C13—H13C0.9800
O5—C191.417 (4)C14—C151.524 (4)
O5—C141.423 (3)C14—H14A0.9900
O6—C191.423 (4)C14—H14B0.9900
O6—C161.435 (3)C15—C181.529 (4)
O7—C171.431 (4)C15—C171.533 (4)
O7—H70.8400C15—C161.534 (4)
O8—C181.424 (4)C16—H16A0.9900
O8—H80.8400C16—H16B0.9900
C1—C21.520 (4)C17—H17A0.9900
C1—H1A0.9900C17—H17B0.9900
C1—H1B0.9900C18—H18A0.9900
C2—C31.526 (4)C18—H18B0.9900
C2—C51.527 (4)C19—C201.505 (4)
C2—C41.537 (4)C19—H19A1.0000
C3—H3A0.9900C20—C211.523 (4)
C3—H3B0.9900C20—H20A0.9900
C4—H4A0.9900C20—H20B0.9900
C4—H4B0.9900C21—C221.525 (4)
C5—H5A0.9900C21—H21A0.9900
C5—H5B0.9900C21—H21B0.9900
C6—C71.509 (4)C22—C231.521 (4)
C6—H6A1.0000C22—H22A0.9900
C7—C81.525 (4)C22—H22B0.9900
C7—H7A0.9900C23—C241.526 (4)
C7—H7B0.9900C23—H23A0.9900
C8—C91.520 (4)C23—H23B0.9900
C8—H8A0.9900C24—C251.518 (5)
C8—H8B0.9900C24—H24A0.9900
C9—C101.529 (4)C24—H24B0.9900
C9—H9A0.9900C25—C261.524 (5)
C9—H9B0.9900C25—H25A0.9900
C10—C111.519 (4)C25—H25B0.9900
C10—H10A0.9900C26—H26A0.9800
C10—H10B0.9900C26—H26B0.9800
C11—C121.517 (5)C26—H26C0.9800
C6—O1—C1110.9 (2)H13A—C13—H13B109.5
C6—O2—C3110.4 (2)C12—C13—H13C109.5
C5—O3—H3109.5H13A—C13—H13C109.5
C4—O4—H4109.5H13B—C13—H13C109.5
C19—O5—C14112.0 (2)O5—C14—C15111.6 (2)
C19—O6—C16111.3 (2)O5—C14—H14A109.3
C17—O7—H7109.5C15—C14—H14A109.3
C18—O8—H8109.5O5—C14—H14B109.3
O1—C1—C2111.5 (2)C15—C14—H14B109.3
O1—C1—H1A109.3H14A—C14—H14B108.0
C2—C1—H1A109.3C14—C15—C18111.1 (2)
O1—C1—H1B109.3C14—C15—C17107.8 (2)
C2—C1—H1B109.3C18—C15—C17110.0 (2)
H1A—C1—H1B108.0C14—C15—C16107.1 (2)
C1—C2—C3108.1 (2)C18—C15—C16109.2 (3)
C1—C2—C5108.0 (2)C17—C15—C16111.6 (2)
C3—C2—C5110.1 (2)O6—C16—C15110.4 (2)
C1—C2—C4111.1 (2)O6—C16—H16A109.6
C3—C2—C4109.5 (2)C15—C16—H16A109.6
C5—C2—C4110.0 (2)O6—C16—H16B109.6
O2—C3—C2111.2 (2)C15—C16—H16B109.6
O2—C3—H3A109.4H16A—C16—H16B108.1
C2—C3—H3A109.4O7—C17—C15112.3 (2)
O2—C3—H3B109.4O7—C17—H17A109.1
C2—C3—H3B109.4C15—C17—H17A109.1
H3A—C3—H3B108.0O7—C17—H17B109.1
O4—C4—C2110.8 (3)C15—C17—H17B109.1
O4—C4—H4A109.5H17A—C17—H17B107.9
C2—C4—H4A109.5O8—C18—C15112.3 (3)
O4—C4—H4B109.5O8—C18—H18A109.1
C2—C4—H4B109.5C15—C18—H18A109.1
H4A—C4—H4B108.1O8—C18—H18B109.1
O3—C5—C2112.3 (3)C15—C18—H18B109.1
O3—C5—H5A109.1H18A—C18—H18B107.9
C2—C5—H5A109.1O5—C19—O6110.9 (2)
O3—C5—H5B109.1O5—C19—C20107.7 (2)
C2—C5—H5B109.1O6—C19—C20109.3 (3)
H5A—C5—H5B107.9O5—C19—H19A109.6
O2—C6—O1111.2 (2)O6—C19—H19A109.6
O2—C6—C7108.4 (2)C20—C19—H19A109.6
O1—C6—C7108.1 (2)C19—C20—C21114.8 (3)
O2—C6—H6A109.7C19—C20—H20A108.6
O1—C6—H6A109.7C21—C20—H20A108.6
C7—C6—H6A109.7C19—C20—H20B108.6
C6—C7—C8113.0 (3)C21—C20—H20B108.6
C6—C7—H7A109.0H20A—C20—H20B107.5
C8—C7—H7A109.0C20—C21—C22113.5 (3)
C6—C7—H7B109.0C20—C21—H21A108.9
C8—C7—H7B109.0C22—C21—H21A108.9
H7A—C7—H7B107.8C20—C21—H21B108.9
C9—C8—C7113.3 (3)C22—C21—H21B108.9
C9—C8—H8A108.9H21A—C21—H21B107.7
C7—C8—H8A108.9C23—C22—C21115.2 (3)
C9—C8—H8B108.9C23—C22—H22A108.5
C7—C8—H8B108.9C21—C22—H22A108.5
H8A—C8—H8B107.7C23—C22—H22B108.5
C8—C9—C10113.1 (3)C21—C22—H22B108.5
C8—C9—H9A109.0H22A—C22—H22B107.5
C10—C9—H9B109.0C22—C23—C24113.7 (3)
C8—C9—H9A109.0C22—C23—H23A108.8
C10—C9—H9A109.0C24—C23—H23A108.8
H9A—C9—H9B107.8C22—C23—H23B108.8
C11—C10—C9113.9 (3)C24—C23—H23B108.8
C11—C10—H10A108.8H23A—C23—H23B107.7
C9—C10—H10A108.8C25—C24—C23113.4 (3)
C11—C10—H10B108.8C25—C24—H24A108.9
C9—C10—H10B108.8C23—C24—H24A108.9
H10A—C10—H10B107.7C25—C24—H24B108.9
C12—C11—C10113.4 (3)C23—C24—H24B108.9
C12—C11—H11A108.9H24A—C24—H24B107.7
C10—C11—H11A108.9C24—C25—C26114.3 (3)
C12—C11—H11B108.9C24—C25—H25A108.7
C10—C11—H11B108.9C26—C25—H25A108.7
H11A—C11—H11B107.7C24—C25—H25B108.7
C11—C12—C13113.6 (3)C26—C25—H25B108.7
C11—C12—H12A108.9H25A—C25—H25B107.6
C13—C12—H12A108.9C25—C26—H26A109.5
C11—C12—H12B108.9C25—C26—H26B109.5
C13—C12—H12B108.9H26A—C26—H26B109.5
H12A—C12—H12B107.7C25—C26—H26C109.5
C12—C13—H13A109.5H26A—C26—H26C109.5
C12—C13—H13B109.5H26B—C26—H26C109.5
C6—O1—C1—C2−56.8 (3)C19—O5—C14—C1557.2 (3)
O1—C1—C2—C351.2 (3)O5—C14—C15—C1866.1 (3)
O1—C1—C2—C5170.2 (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—C257.9 (3)C19—O6—C16—C15−59.0 (3)
C1—C2—C3—O2−51.7 (3)C14—C15—C16—O653.9 (3)
C5—C2—C3—O2−169.5 (2)C18—C15—C16—O6−66.5 (3)
C4—C2—C3—O269.5 (3)C17—C15—C16—O6171.7 (2)
C1—C2—C4—O4−66.5 (3)C14—C15—C17—O7−167.6 (2)
C3—C2—C4—O4174.1 (2)C18—C15—C17—O7−46.3 (3)
C5—C2—C4—O453.0 (3)C16—C15—C17—O775.1 (3)
C1—C2—C5—O3174.5 (2)C14—C15—C18—O860.5 (3)
C3—C2—C5—O3−67.6 (3)C17—C15—C18—O8−58.8 (3)
C4—C2—C5—O353.1 (3)C16—C15—C18—O8178.4 (2)
C3—O2—C6—O1−62.5 (3)C14—O5—C19—O6−59.6 (3)
C3—O2—C6—C7178.8 (2)C14—O5—C19—C20−179.1 (2)
C1—O1—C6—O262.1 (3)C16—O6—C19—O560.7 (3)
C1—O1—C6—C7−179.0 (2)C16—O6—C19—C20179.3 (2)
O2—C6—C7—C8−174.7 (2)O5—C19—C20—C21−176.5 (3)
O1—C6—C7—C864.6 (3)O6—C19—C20—C2162.9 (3)
C6—C7—C8—C9−178.5 (3)C19—C20—C21—C22−169.5 (3)
C7—C8—C9—C10179.4 (3)C20—C21—C22—C23−60.4 (4)
C8—C9—C10—C11179.4 (3)C21—C22—C23—C24177.3 (3)
C9—C10—C11—C12179.2 (3)C22—C23—C24—C25180.0 (3)
C10—C11—C12—C13179.5 (3)C23—C24—C25—C26179.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O70.841.942.736 (3)159
O4—H4···O3i0.841.822.656 (3)171
O7—H7···O8ii0.841.822.646 (3)167
O8—H8···O40.841.922.701 (3)155

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5378).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2003). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Luo, Y.-M., Liu, X.-M., Yuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1536. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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