organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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1,2,3,4,5,6-Hexa-O-acetyl-scyllo-inositol

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bNatural Product Microbes Division, Indian, Institute of Integrative Medicine, Canal Road, Jammu Tawi 180 001, India
*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 6 July 2012; accepted 25 July 2012; online 28 July 2012)

The title mol­ecule, C18H24O12, has crystallographic 2/m symmetry with two acetate group located on a mirror plane. The H—Csp3—O—Csp2 torsion angles characterizing orientation of the acetyl groups with respect to the cyclo­hexane ring are 0.0, 23.9 and −23.9°. The cyclo­hexane ring is in a chair conformation with all substituents in equatorial positions. In the crystal, mol­ecules are connected through C—H⋯O hydrogen bonds into a chain extending along the c axis.

Related literature

For applications of the title compound, see: Kamal & Mathur (1991[Kamal, R. & Mathur, N. (1991). J. Phytol. Res. 4, 213-214.]); Anonymous et al. (2001[Anonymous (2001). The Wealth of India (Raw Materials Series), Vol. VII p. 268. New Delhi: NISCOM.], 2003[Anonymous (2003). The Wealth of India (Raw Materials Series), Vol. IV, pp. 282-284. New Delhi: NISCOM.]). For related structures, see: Abboud et al. (1990[Abboud, K. A., Simonsen, S. H., Voll, R. J. & Younathan, E. S. (1990). Acta Cryst. C46, 2208-2210.]).

[Scheme 1]

Experimental

Crystal data
  • C18H24O12

  • Mr = 432.37

  • Monoclinic, C 2/m

  • a = 12.901 (3) Å

  • b = 14.013 (3) Å

  • c = 5.8572 (12) Å

  • β = 97.33 (2)°

  • V = 1050.2 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.472, Tmax = 1.000

  • 3652 measured reflections

  • 959 independent reflections

  • 626 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.198

  • S = 1.08

  • 959 reflections

  • 77 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1⋯O4i 0.98 2.57 3.393 (4) 141
Symmetry code: (i) x, -y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Parthenium hysterophorus (Asteraceae) is an annual weed. It is commonly known as congress weed, carrot weed, star weed, feverfew etc. A decoction of the root of P. hysterophorus finds use in treatment of dysentery (Anonymous et al., 2001). Histamine (0.35%) is present in the roots of plant (Kamal & Mathur, 1991). The roots contain parthenin, caffeic, chlorogenic, p-hydroxybenzoic, p-anisic, vanilic, salicylic, gentisic, neo-chlorogenic and proto-catechuic acids (Anonymous et al., 2003). Roots of this plant were not that much explored thus making this an interesting field to carry out further studies.

In the title compound (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related structure (Abboud et al., 1990). The twist angles characterizing orientation of the acetyl group with respect to the cyclohexane ring are: H1—C1—O2—C3 = -23.9°, H2—C2—O1—C5 = 0.0°. The cyclohexyl ring is in the chair conformation. Intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains along the c axis..

Related literature top

For applications of the title compound, see: Kamal & Mathur (1991); Anonymous et al. (2001, 2003). For related structures, see: Abboud et al. (1990).

Experimental top

Dried roots (2 kg) of P. hysterophorus was crushed, water extract was prepared and lyophilized. Dry powder (5 g) obtained was treated with pyridine (50 ml) and acetic anhydride (60 ml) and was stirred at room temperature. Progress of the reaction was checked by TLC. After completion of the reaction, mixture was treated dropwise with 1.5 N aqueous HCl (50 ml) and then extracted with ethyl acetate (3x100mL). After usual workup and removal of the solvents the reaction product obtained was 8 g. Chromatographic separation of the products on a silica gel column using chloroform: methanol (99:1 to 80:20) as eluent, gave pure myo-inositol hexaacetate and later fractions gave scyllo-inositol hexaacetate as white crystals m.p. 651–653 K. Single crystal of the compound was grown by slow evaporation technique using methanol /chloroform as the solvent system.

Refinement top

All H atoms (except methyl C6 H) were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.96–0.98 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Structure description top

Parthenium hysterophorus (Asteraceae) is an annual weed. It is commonly known as congress weed, carrot weed, star weed, feverfew etc. A decoction of the root of P. hysterophorus finds use in treatment of dysentery (Anonymous et al., 2001). Histamine (0.35%) is present in the roots of plant (Kamal & Mathur, 1991). The roots contain parthenin, caffeic, chlorogenic, p-hydroxybenzoic, p-anisic, vanilic, salicylic, gentisic, neo-chlorogenic and proto-catechuic acids (Anonymous et al., 2003). Roots of this plant were not that much explored thus making this an interesting field to carry out further studies.

In the title compound (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related structure (Abboud et al., 1990). The twist angles characterizing orientation of the acetyl group with respect to the cyclohexane ring are: H1—C1—O2—C3 = -23.9°, H2—C2—O1—C5 = 0.0°. The cyclohexyl ring is in the chair conformation. Intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains along the c axis..

For applications of the title compound, see: Kamal & Mathur (1991); Anonymous et al. (2001, 2003). For related structures, see: Abboud et al. (1990).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Symmetry operations generating the whole molecule from the asymmetric part are: 1-x, -y, 1-z and x, -y, z.
[Figure 2] Fig. 2. The packing arrangement of molecules viewed down the a axis. For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.
1,2,3,4,5,6-Hexa-O-acetyl-scyllo-inositol top
Crystal data top
C18H24O12F(000) = 456
Mr = 432.37Dx = 1.367 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yCell parameters from 1553 reflections
a = 12.901 (3) Åθ = 3.5–29.1°
b = 14.013 (3) ŵ = 0.12 mm1
c = 5.8572 (12) ÅT = 293 K
β = 97.33 (2)°Block, white
V = 1050.2 (4) Å30.3 × 0.2 × 0.2 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
959 independent reflections
Radiation source: fine-focus sealed tube626 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 16.1049 pixels mm-1θmax = 25.0°, θmin = 3.5°
ω scanh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 1616
Tmin = 0.472, Tmax = 1.000l = 66
3652 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1032P)2P]
where P = (Fo2 + 2Fc2)/3
959 reflections(Δ/σ)max = 0.001
77 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C18H24O12V = 1050.2 (4) Å3
Mr = 432.37Z = 2
Monoclinic, C2/mMo Kα radiation
a = 12.901 (3) ŵ = 0.12 mm1
b = 14.013 (3) ÅT = 293 K
c = 5.8572 (12) Å0.3 × 0.2 × 0.2 mm
β = 97.33 (2)°
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
959 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
626 reflections with I > 2σ(I)
Tmin = 0.472, Tmax = 1.000Rint = 0.081
3652 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.198H-atom parameters constrained
S = 1.08Δρmax = 0.37 e Å3
959 reflectionsΔρmin = 0.30 e Å3
77 parameters
Special details top

Experimental. Absorption correction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3027 (2)0.00000.6341 (4)0.0412 (8)
O20.42280 (15)0.16670 (15)0.6695 (3)0.0448 (7)
O30.3640 (2)0.26466 (17)0.3790 (4)0.0660 (8)
O40.3169 (3)0.00001.0179 (5)0.0722 (12)
C10.4426 (2)0.0905 (2)0.5150 (4)0.0373 (8)
H10.39910.09780.36620.045*
C20.4142 (3)0.00000.6355 (6)0.0376 (10)
H20.44850.00000.79470.045*
C30.3838 (2)0.2500 (2)0.5799 (6)0.0483 (9)
C40.3714 (3)0.3192 (3)0.7664 (6)0.0695 (12)
H4A0.43600.35260.80800.104*
H4B0.35270.28570.89810.104*
H4C0.31740.36410.71360.104*
C50.2635 (4)0.00000.8365 (8)0.0450 (11)
C60.1486 (4)0.00000.7967 (8)0.0566 (13)
H6A0.12570.00000.63420.085*
H6B0.12260.05590.86500.085*0.50
H6C0.12260.05590.86500.085*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0386 (16)0.0466 (18)0.0389 (16)0.0000.0071 (12)0.000
O20.0514 (14)0.0377 (13)0.0449 (12)0.0038 (10)0.0042 (10)0.0055 (9)
O30.0836 (19)0.0463 (15)0.0667 (17)0.0192 (14)0.0036 (13)0.0052 (12)
O40.078 (3)0.095 (3)0.045 (2)0.0000.0124 (17)0.000
C10.0416 (17)0.0317 (16)0.0377 (16)0.0024 (14)0.0020 (13)0.0030 (12)
C20.040 (2)0.034 (2)0.038 (2)0.0000.0020 (16)0.000
C30.0431 (18)0.0376 (19)0.063 (2)0.0026 (15)0.0026 (15)0.0027 (15)
C40.071 (2)0.050 (2)0.086 (3)0.006 (2)0.001 (2)0.0216 (19)
C50.057 (3)0.031 (2)0.049 (3)0.0000.016 (2)0.000
C60.056 (3)0.044 (3)0.076 (3)0.0000.029 (2)0.000
Geometric parameters (Å, º) top
O1—C51.347 (5)C2—H20.9800
O1—C21.438 (5)C3—C41.485 (4)
O2—C31.350 (4)C4—H4A0.9600
O2—C11.443 (3)C4—H4B0.9600
O3—C31.189 (4)C4—H4C0.9600
O4—C51.190 (5)C5—C61.471 (6)
C1—C1i1.514 (5)C6—H6A0.9600
C1—C21.519 (3)C6—H6B0.9600
C1—H10.9800C6—H6C0.9600
C2—C1ii1.519 (3)
C5—O1—C2118.8 (3)O2—C3—C4110.4 (3)
C3—O2—C1118.8 (2)C3—C4—H4A109.5
O2—C1—C1i109.09 (19)C3—C4—H4B109.5
O2—C1—C2104.7 (2)H4A—C4—H4B109.5
C1i—C1—C2110.6 (2)C3—C4—H4C109.5
O2—C1—H1110.8H4A—C4—H4C109.5
C1i—C1—H1110.8H4B—C4—H4C109.5
C2—C1—H1110.8O4—C5—O1123.1 (4)
O1—C2—C1ii107.3 (2)O4—C5—C6126.7 (4)
O1—C2—C1107.3 (2)O1—C5—C6110.1 (4)
C1ii—C2—C1113.3 (3)C5—C6—H6A109.5
O1—C2—H2109.6C5—C6—H6B109.5
C1ii—C2—H2109.6H6A—C6—H6B109.5
C1—C2—H2109.6C5—C6—H6C109.5
O3—C3—O2123.8 (3)H6A—C6—H6C109.5
O3—C3—C4125.8 (3)H6B—C6—H6C109.5
C3—O2—C1—C1i98.2 (3)O2—C1—C2—C1ii172.6 (2)
C3—O2—C1—C2143.4 (3)C1i—C1—C2—C1ii55.2 (4)
C5—O1—C2—C1ii119.0 (2)C1—O2—C3—O30.4 (5)
C5—O1—C2—C1119.0 (2)C1—O2—C3—C4178.8 (2)
O2—C1—C2—O169.1 (3)C2—O1—C5—O40.0
C1i—C1—C2—O1173.5 (2)C2—O1—C5—C6180.0
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O4iii0.982.573.393 (4)141
Symmetry code: (iii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC18H24O12
Mr432.37
Crystal system, space groupMonoclinic, C2/m
Temperature (K)293
a, b, c (Å)12.901 (3), 14.013 (3), 5.8572 (12)
β (°) 97.33 (2)
V3)1050.2 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire3
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.472, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
3652, 959, 626
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.198, 1.08
No. of reflections959
No. of parameters77
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O4i0.982.573.393 (4)141
Symmetry code: (i) x, y, z1.
 

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

First citationAbboud, K. A., Simonsen, S. H., Voll, R. J. & Younathan, E. S. (1990). Acta Cryst. C46, 2208–2210.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationAnonymous (2001). The Wealth of India (Raw Materials Series), Vol. VII p. 268. New Delhi: NISCOM.  Google Scholar
First citationAnonymous (2003). The Wealth of India (Raw Materials Series), Vol. IV, pp. 282-284. New Delhi: NISCOM.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationKamal, R. & Mathur, N. (1991). J. Phytol. Res. 4, 213–214.  Google Scholar
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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